But as it turned out, Trout wasn't actually the top earner in global sports. Quietly, over in Spain, Lionel Messi was playing under a contract with FC Barcelona that dwarfed Trout's in every way. In January 2021, the Spanish newspaper El Mundo leaked the details of Messi's four-year deal, revealing a staggering $674 million package. The revelation sent shockwaves through the sports world. Messi's average annual salary during that period was an unprecedented $168.5 million. So in reality, Messi, not Trout, held the crown for the richest sports contract of all time up to that point.

That record stood until December 9, 2023, when Shohei Ohtani signed a 10-year, $700 million contract with the Los Angeles Dodgers. It was the largest total contract in professional sports history, at least by headline value. And that record was broken just two years later by Juan Soto!

Interestingly, neither Messi nor Ohtani holds the record for highest average annual salary. That distinction belongs to Cristiano Ronaldo and Karim Benzema, in a statistical tie. Both soccer superstars signed contracts with Saudi Arabian clubs that average out to $214.5 million per year. Cristiano's 2.5-year, $536 million deal with Al-Nassr and Karim's 2-year, $436 million deal with Al-Ittihad include base salaries and massive commercial incentives. When adjusted for term length, each contract averages exactly $214,534,727 per year—the highest in history.

So, who else makes the list of the most lucrative contracts ever handed out in professional sports? The rankings below are based on total contract value at the time the deals were signed, regardless of whether the full amount was ultimately paid or if the player is still with the original team.

In total, this list includes 43 contracts signed by 42 different athletes (with Alex Rodriguez appearing twice). The majority come from Major League Baseball, which accounts for 26 of the 43 entries. The rest are spread across American football (8 contracts), basketball (4 contracts), soccer (5 contracts), boxing (1 contract), and Formula 1 (1 contract).

As of June 2025, 25 of these contracts are still active, while 18 have either expired, been terminated, or the player has retired.

The Largest Sports Contracts Of All Time

The following amounts are ranked in order of overall contract value.

#1: Juan Soto, New York Mets – 15 years, $765 million

In late 2024, Juan Soto signed a 15-year, $765 million deal with the New York Mets. The massive extension locks in the 26-year-old superstar through his age-40 season and resets the ceiling for long-term baseball contracts. Known for his elite plate discipline and postseason performance, Soto's deal shattered the previous record set by Shohei Ohtani just two years earlier.

#2: Shohei Ohtani, LA Dodgers, 10 years, $700 million

Shohei Ohtani made history on December 9, 2023, by signing a 10-year, $700 million contract with the Los Angeles Dodgers, becoming the highest-paid athlete in baseball history.

The deal surpasses Mike Trout's 12-year, $426 million contract with the Angels, which was previously the largest in baseball history. Ohtani's average annual salary of $70 million will nearly double the roughly $42.3 million he earned with the Angels.

Ohtani's unique skillset as a dominant pitcher and hitter made him a highly sought-after free agent. He was heavily pursued by several teams, including the Angels, Mets, and Yankees, but ultimately chose the Dodgers.

#3: Kylian Mbappé, Paris Saint-Germain – 3 years, $681 million

In 2022, Kylian Mbappé signed a groundbreaking three-year contract extension with Paris Saint-Germain, valued at approximately $681 million. The deal included a $180 million signing bonus and a substantial annual salary, making it one of the most lucrative contracts in sports history. Mbappé's decision to stay with PSG, despite interest from other top European clubs, underscored his commitment to the team's ambitious project.

#4: Lionel Messi, FC Barcelona – 4 years, $674 million

In 2017, Lionel Messi signed a four-year contract with FC Barcelona worth an astounding $674 million, a figure that made it the most lucrative sports contract in history up to that point. The deal, leaked to the Spanish newspaper El Mundo, sent shockwaves through the sports world, sparking debates about financial disparity and the future of professional football.

The contract included a fixed salary, image rights, and a series of performance-based bonuses. On an annual basis, Lionel earned $168.5 million.

#5: Neymar, Paris Saint-Germain – 6 years, $595 million

In August 2017, Neymar made headlines by transferring from FC Barcelona to Paris Saint-Germain for a record-breaking $263 million transfer fee. He then signed a six-year contract with PSG, which, including wages and bonuses, amounted to approximately $595 million. This move not only set a new benchmark for player transfers but also significantly impacted the football economy, leading to increased scrutiny over financial regulations in the sport.

#6: Cristiano Ronaldo, Al-Nassr – 2.5 years, $536 million

In December 2022, Cristiano Ronaldo surprised the football world by signing a 2.5-year contract with Saudi Arabian club Al Nassr, worth a staggering $536 million. This deal cemented his position as the world's highest-paid athlete and marked a significant turning point in his illustrious career.

The contract details are fascinating. While the reported base salary is $75 million per year, the total value is inflated by lucrative bonuses and commercial deals, potentially reaching $200 million annually. This astronomical sum reflects Ronaldo's enduring global brand value and the Saudi Arabian league's ambition to attract top talent.

#7: Patrick Mahomes, Kansas City Chiefs – 10 years, $503 million

Patrick Mahomes won the NFL MVP award in 2018. The following season, he won both the Super Bowl AND Super Bowl MVP. Perhaps not surprisingly, those accomplishments made the Kansas City Chiefs EXTREMELY eager to lock their 24-year-old star QB up long term. Initial predictions assumed his extension would top $250 million. That prediction ended up being true, but it was also off by an incredible amount. On July 6, 2020, it was announced that Patrick signed a 10-year, $503 million deal with the Chiefs. It is the first professional sports contract to crack the half-billion mark.

The 10-year extension includes $477 million in guarantee mechanisms, plus the ability for Mahomes to get out of the contract if those mechanisms aren't exercised.

The contract also has a $140 million injury guarantee. So if he had a career-ending injury on day one of his first season, he would still earn $140 million.

Fun Fact: Alex Rodriguez has TWO record contracts on the list below. The first record contract A-Rod set came in 2000 when he signed a 10-year, $252 million deal with the Texas Rangers. One of Alex's Ranger teammates at the time was Patrick Mahomes Sr, a pitcher. Patrick Jr would have been around six years old at the time. Imagine telling that six-year-old (and his father) that in almost exactly 20 years, you'll sign a contract TWICE as valuable as A-Rod's…

#8: Vladimir Guerrero Jr., Toronto Blue Jays – 14 years, $500 million

On April 2, 2025, Vladimir Guerrero Jr. signed a jaw-dropping 14-year, $500 million contract extension with the Toronto Blue Jays, making it the largest contract in baseball history by net present value. The deal locks in the All-Star slugger through his age-39 season and solidifies his place as the long-term face of the franchise. Guerrero had already established himself as one of the game's premier power hitters and a perennial MVP candidate, and this extension reflects Toronto's confidence in building their future around him. While the total value of Shohei Ohtani's Dodgers deal is technically higher, much of that money is deferred, making Vlad's contract arguably the richest in real dollar terms.

#9: Karim Benzema, Al-Ittihad Club – 2 years, $436 million

As we mentioned previously, Karim's contract, which he signed in June 2023, was a 2-year, $436 million contract with Saudi soccer club Al-Ittihad. On a per-year average salary basis, he earns $214,534,727, exactly the same amount earned by Cristiano Ronaldo in terms of average annual salary. And that amount is the highest average annual salary earned by any athlete in history.

#10: Mike Trout, Los Angeles Angels – 12 years, $430 million

Since becoming a full-time major leaguer in 2012, Trout has made seven All-Star teams and won two AL MVP awards. However, it hasn't translated to much team success. The Angels have made the playoffs just once in that span, getting swept during the 2014 postseason. Trout will have to lead the Angels on multiple deep playoff runs to truly make this a worthwhile deal. It's probably not fair to put so much weight on one player's shoulders, but then again, no one's ever made this much money before.

#11 (tie): Canelo Alvarez, DAZN – 5 years, $365 million

Trout may hold the record for most overall money, but Alvarez blows him out of the water when it comes to annual salary. The boxer signed a five-year, 11-fight deal last October with the streaming service DAZN. The contract will pay him a whopping $73 million per year, with each fight being worth about $33.18 million.

#11: Mookie Betts, LA Dodgers – 12 years, $365 million

Betts, a former MVP, signed this extension in 2020, solidifying his role as a cornerstone for the Dodgers' future.

#12: Aaron Judge, NY Yankees – 9 years, $360 million

Judge's contract, signed in December 2022, followed his record-breaking 62-home run season, the highest in American League history."

#13: Manny Machado, San Diego Padres – 11 years, $350 million

Remember when Machado had the biggest deal of the 2019 MLB offseason? Seems like so long ago. The Padres have struggled mightily in relative anonymity for the past decade, so signing a star like Machado is a huge deal. There's a catch, though: Machado can opt out after five seasons. If he doesn't like the state of the team at that point, the Padres will lose him for nothing. As of 2025, Machado has not exercised his opt-out clause, remaining with the Padres.

#14: Francisco Lindor, NY Mets – 10 years, $341 million

#15: Fernando Tatis Jr., San Diego Padres – 14 years, $340 million

#16 (tie): Max Verstappen, Red Bull Racing – 6 years, $330 million

#16: (tie) Bryce Harper, Philadelphia Phillies – 13 years, $330 million

After Harper signed his deal, it was only a matter of time before his buddy Trout got a major extension, too. Harper's free agency saga dragged out for nearly the entire offseason; he signed just about a month before Opening Day. Eventually, he left Washington to join an NL East rival. The Phillies made back-to-back World Series appearances in 2008 and 2009, but haven't had a winning record since 2011. Harper is expected to immediately help turn the team's fortunes around.

#17: (tie): Yoshinobu Yamamoto, LA Dodgers – 12 years, $325 million

#17 (tie) Corey Seager, Texas Rangers – 10 years, $325 million

#17: (tie) Giancarlo Stanton, Miami Marlins – 13 years, $325 million

This is the largest contract on this list that wasn't signed within the past year. Stanton re-signed with the Marlins on this massive deal but was dealt to the Yankees just two seasons later. That means the Bronx Bombers are picking up the majority of the tab on Stanton. However, if Stanton doesn't opt out of his contract after the 2020 season, the Yankees will receive $30 million in salary cap relief from the Marlins.

#18: Gerrit Cole, New York Yankees – 9 years, $324 million

The three-time All-Star pitcher played for four seasons for the Pirates from 2013-2017, then two seasons with the Houston Astros from 2018-2019. Ahead of the 2020 season, Gerrit signed a 9-year, $324 million monster contract with the Yankees.

#19: Rafael Devers, Boston Red Sox – 10 years, $313.5 million

The Red Sox locked up their franchise third baseman in January 2023 with a 10-year, $313.5 million extension. At just 26 years old at the time, Devers was rewarded for his consistent offensive production and became one of the highest-paid infielders in league history.

#20: Jayson Tatum, Boston Celtics – 5 years, $314 million

In 2025, Jayson Tatum signed the richest contract in NBA history, a five-year, $314 million supermax extension with the Boston Celtics. The deal came after multiple All-Star appearances and deep playoff runs, cementing Tatum as the face of the franchise well into the next decade.

#21: Jaylen Brown, Boston Celtics – 5 years, $303.7 million

Before Tatum broke the record, it was Brown who briefly held the title for the NBA's richest contract. In 2023, the Celtics signed him to a five-year, $303.7 million supermax extension, reflecting his rise to elite two-way status and the league's skyrocketing salary cap.

#22: Trea Turner, Philadelphia Phillies – 11 years, $300 million

The Phillies continued their big-spending approach by inking All-Star shortstop Trea Turner to an 11-year, $300 million contract in December 2022. Known for his elite speed, defense, and contact hitting, Turner's deal reunites him with Bryce Harper and pushes Philadelphia's payroll into the stratosphere.

#23: Bobby Witt Jr., Kansas City Royals – 11 years, $288.7 million

In February 2024, the Royals stunned the baseball world by signing 23-year-old Bobby Witt Jr. to an 11-year, $288.7 million extension—the largest deal in franchise history by far. Witt, already one of the most exciting young players in the game, signaled Kansas City's desire to build a long-term contender.

#24: Xander Bogaerts, San Diego Padres – 11 years, $280 million

The Padres made another massive free agency splash in December 2022, signing veteran shortstop Xander Bogaerts to an 11-year, $280 million deal. The former Red Sox star brought championship pedigree and offensive consistency to a star-studded San Diego roster.

#25: Alex Rodriguez, New York Yankees – 10 years, $275 million

A-Rod opted out of his existing deal in 2007 to sign a 10-year, $275 million extension with the New York Yankees. The end of Rodriguez's career was marred by injury and scandal. And throughout his stay, he was a polarizing figure in New York, especially playing next to hometown hero Derek Jeter. But Rodriguez did collect his only World Series ring during this contract, helping the Yankees beat the Phillies in 2009. It's the franchise's last World Series victory.

#26: (tie) Joe Burrow, Cincinnati Bengals – 5 years, $275 million

In September 2023, Joe Burrow became the highest-paid player in NFL history (briefly) when he signed a five-year, $275 million extension with the Bengals. The deal included $219 million guaranteed and cemented Burrow as Cincinnati's long-term franchise quarterback.

#26 (tie): Trevor Lawrence, Jacksonville Jaguars – 5 years, $275 million

Just months after Burrow's deal, Trevor Lawrence signed a matching five-year, $275 million extension with the Jaguars in 2024. The former No. 1 pick had led Jacksonville to back-to-back playoff appearances, earning the massive commitment from the franchise.

#27: Nikola Jokić, Denver Nuggets – 5 years, $264 million

Fresh off winning back-to-back MVP awards, Jokić signed a five-year, $264 million supermax extension with the Nuggets in 2022. It was the richest deal in NBA history at the time and underscored Denver's commitment to its Serbian superstar.

#28: Justin Herbert, LA Chargers – 5 years, $262.5 million

In July 2023, the Chargers secured their franchise QB with a five-year, $262.5 million extension. The deal briefly made Herbert the highest-paid player in the NFL until Burrow and Lawrence leapfrogged him shortly after.

#29: Nolan Arenado, Colorado Rockies – 8 years, $260 million

In February 2019, Nolan Arenado signed an eight-year, $260 million extension with the Colorado Rockies, briefly making him the highest-paid position player in MLB history by average annual value. The deal included full no-trade protection and an opt-out clause after the 2021 season. Despite the long-term commitment, the relationship between Arenado and the Rockies quickly soured, largely due to front office turmoil and a lack of postseason ambition.

Just two years into the contract, the Rockies traded Arenado to the St. Louis Cardinals ahead of the 2021 season—along with $50 million in cash—to offload salary. With the Cardinals, Arenado has remained one of the league's elite third basemen, adding multiple Gold Gloves and All-Star appearances to his résumé. While the contract was originally signed with Colorado, most of its value has ultimately been paid by St. Louis.

#30: Josh Allen, Buffalo Bills – 6 years, $258 million

In August 2021, Allen became the first quarterback in the loaded 2018 draft class to cash in, signing a six-year, $258 million extension with the Bills. It marked Buffalo's biggest contract ever and positioned Allen as the centerpiece of their championship aspirations.

#31: Jalen Hurts, Philadelphia Eagles – 5 years, $255 million

In April 2023, the Eagles rewarded Hurts with a five-year, $255 million deal following his breakout 2022 season and Super Bowl appearance. For a brief moment, he held the NFL's record for highest average annual salary before being surpassed by Herbert and Burrow.

#32: Alex Rodriguez, Texas Rangers – 10 years, $252 million

Rodriguez is the only player to appear twice on this list. This deal in 2000 set the bar for massive MLB contracts. He ultimately only spent three years with the Rangers, winning the AL MVP award in 2003 but failing to make the playoffs during his tenure with the team. The Rangers traded Rodriguez to the Yankees before the 2004 season. Four years later, he signed a new (at the time) record-setting deal to stay in New York.  

#33: Miguel Cabrera, Detroit Tigers – 8 years, $247 million

Cabrera's contract is a bit different than some of the others on this list in that it kicked in after he was past his prime. In 2014, the Tigers offered their star first baseman an eight-year extension starting in 2016. Cabrera was 33 when the deal began, and he'll be in his forties when it ends. Injury is also a risk – Cabrera spent most of 2017 playing with two herniated discs in his back, and played just 38 games last season due to hamstring and biceps injuries.

#34: Anthony Rendon, Los Angeles Angels – 7 years, $245 million

#35: Stephen Strasburg, Washington Nationals – 7 years, $245 million

#36: Russell Wilson, Denver Broncos – 5 years, $242.6 million

Acquired in a blockbuster trade from Seattle, Russell Wilson signed a five-year, $242.6 million extension with the Denver Broncos in 2022. The deal was intended to kickstart a new era in Denver, though early results were rocky.

#37: Albert Pujols, Los Angeles Angels – 10 years, $240 million

In 11 seasons with the St. Louis Cardinals, Pujols made nine All-Star teams and won three MVP awards. He also led the league in runs scored five times, slugging and on-base percentage three times each, home runs twice, and batting average once. Since signing this deal with the Angels in 2012, Pujols has made just one All-Star team, in 2015. And the only statistical categories he's led the league in? Grounding into double plays, which he's done twice (in 2014 and 2017). Pujols also hasn't hit higher than .285 since joining the Angels. He's still a future Hall of Famer, but it'll be largely based on what he did before signing this contract.

#38: Robinson Cano, Seattle Mariners – 10 years, $240 million

Before the 2014 season, Cano signed this deal with the Mariners. He turned down a seven-year, $175 million contract to stay with the Yankees. Cano did make three All-Star appearances in five seasons with the Mariners, but he was suspended 80 games last year for the use of performance-enhancing drugs. The Mariners traded him to the Mets this offseason. Cano promptly hit a home run in his first at-bat with his new team.

Read more: The Largest Contracts In Professional Sports History

But Odom's life off the court has often been defined by instability, addiction, and financial and personal turmoil. And in recent months, his name has resurfaced not because of a comeback, but because of a court-ordered eviction and an awkward appearance at a controversial crypto dinner hosted by Donald Trump.

So what happened to one of the most versatile forwards of his era?

Trouble Before the Spotlight

When trying to dissect the fall of Lamar Odom, some will point to his upbringing. It wasn't the best. He was raised by his grandmother after his mother passed away from colon cancer when he was just 12 years old. His father was a heroin addict and wasn't a consistent presence in his life until Odom started making millions in the NBA.

Initially, he planned to play college basketball at UNLV, even enrolling in summer classes in 1997. But the school released him after questions arose about his unusually high ACT score (22 out of 36). During his brief time at UNLV, Odom was arrested for soliciting a prostitute in an undercover Las Vegas PD operation. It was later discovered that he accepted payments totaling $5,600 from a booster, further complicating his eligibility.

He transferred to the University of Rhode Island, sat out the 1997–98 season, and then delivered a standout performance during the 1998–99 season. Odom helped the Rams win the Atlantic 10 championship and hit a buzzer-beating game-winner in the tournament final.

Early NBA Success and Red Flags

Odom declared for the 1999 NBA Draft and was taken fourth overall by the Los Angeles Clippers. He signed a three-year deal worth $7.88 million and earned First-Team All-Rookie honors. But by his second season, warning signs emerged. He was suspended for his second drug-related offense in just eight months, later admitting to marijuana use. His performance dipped. He played only 29 games that season and just 49 the next. The Clippers declined to re-sign him.

He found new life with the Miami Heat during the 2003–04 season, posting a career-best 17.1 points and 9.7 rebounds per game. But his biggest value came as a trade chip. In the summer of 2004, he was packaged with Caron Butler and Brian Grant and sent to the Los Angeles Lakers in exchange for Shaquille O'Neal.

Championship Glory and Reality TV Fame

Life was good back in Los Angeles. Odom played out the six-year, $65 million contract he had signed with the Heat, then signed a four-year, $33 million extension with the Lakers in 2009. That same year, he married reality television star Khloé Kardashian and became a fixture on "Keeping Up With the Kardashians." The couple also starred in their own spinoff, "Khloé & Lamar."

By the end of the 2010–11 season, Odom was a two-time NBA champion, a Sixth Man of the Year winner, and a crossover celebrity. But just as his fame reached new heights, his personal and professional life began to spiral.

The Beginning of the End

Odom suffered a string of personal tragedies and setbacks. A cousin he was extremely close to passed away. Days later, he was involved in a car accident that killed a teenager. His grief and emotional state seemed to affect his play. In December 2011, the Lakers traded him to the Dallas Mavericks.

His time in Dallas was a fiasco. He played terribly when he was with the team and even spent some time in the D-League (which he was very unhappy about). After an angry confrontation with Mavericks owner Mark Cuban, who questioned his commitment, he was placed on the inactive list in April 2012.

Dallas traded him to the Clippers, where he played all 82 games of the 2012-13 season, but not well enough to be brought back the following year. His next stop was in a league in Spain during the 2014 season, but an injury cut it short. The Knicks brought him in for part of the 2014 season, but he never actually played in a game.

In total, Lamar earned $115 million during his NBA career from salary alone. Today, we estimate his net worth sits at $20 million, although admittedly, this can be a hard number to nail down when drugs are involved.

More Trouble

His professional decline mirrored his personal one. In August 2013, he was arrested for drunk driving. Rumors of drug abuse swirled in tabloids and online. His marriage became strained. In December 2013, Khloé Kardashian filed for divorce after months of public speculation. Their split wasn't finalized until July 2015.

On October 13, 2015, Odom was found unconscious at the Love Ranch, a legal brothel in Crystal, Nevada. At around 3:15 pm, someone from the establishment called 911, saying he was unconscious and had some strange mucus coming out of his nose and mouth. He couldn't be airlifted to the hospital due to his height, but was eventually transported to the Desert View Hospital, where he was placed on life support. He had suffered a near-fatal overdose, experiencing 12 strokes and six heart attacks while in a coma.

Many feared he wouldn't survive. But after months of hospitalization and a long rehab process, he gradually recovered. Remarkably, he began speaking publicly about his struggles, releasing a memoir, giving interviews, and vowing to stay sober. He even launched Odom Wellness Treatment Centers, a network of rehab facilities aimed at helping others battling addiction.

For a while, it seemed like a true redemption arc was unfolding. He appeared on reality TV again, dabbled in boxing, and spoke candidly about his regrets and lessons learned. But the underlying instability—financial, emotional, and reputational – never seemed far behind.

Back in the Headlines

In May 2025, Odom made headlines again, first for attending a high-profile cryptocurrency dinner hosted by Donald Trump in Virginia. The dinner, designed to reward top investors in Trump's $TRUMP meme coin, was met with vocal protests. As Odom arrived, demonstrators heckled him, yelling "Hypocrite!" and waving signs accusing attendees of corruption. Odom posted a video from the event, seemingly unfazed, and used the opportunity to promote his own meme coin project. It was another puzzling chapter in his unpredictable post-basketball career.

I'm just about to pass through security and officially walk into the Trump Gala.
Honestly… I'm fired up.

Think about it—what meme coin has ever done this?$ODOM isn't just a token, it's taking the stage at a presidential gala tonight!

By the way, Bitcoin is smashing through… pic.twitter.com/7eI5SezPLh

— LAMAR ODOM (@LamarOdom) May 22, 2025

Then, just last week, headlines surfaced claiming that Lamar was ordered to vacate a Studio City mansion after allegedly failing to pay $45,000 in rent. According to court documents, Odom entered a $15,000-per-month rental agreement in late 2024 but failed to make payments for January through March. A judge ordered him to vacate the property after he didn't respond to legal notices.

The Ongoing Paradox of Lamar Odom

At 45, Lamar Odom remains one of the most compelling, conflicted figures to emerge from the NBA in recent decades. His story contains nearly every extreme: poverty and wealth, obscurity and superstardom, devotion and betrayal, triumph and near death. He once stood at the pinnacle of professional sports and pop culture, and now finds himself navigating meme coins, evictions, and occasional public embarrassment. His legacy, like his life, remains a work in progress, a reminder that talent can take you far, but healing is a much harder journey.

Read more: NBA Stardom, A Kardashian Marriage, Brothel Overdoses, Meme Coins and Evictions: The Continually Bizarre Life Lamar Odom

That kind of financial security doesn't exist in football, where contracts are often non-guaranteed and riddled with performance clauses. Even the NBA, where contracts are guaranteed, doesn't quite stack up in career earnings for most players due to shorter average career lengths. Yes, there are exceptions. LeBron James, Kevin Durant, and Stephen Curry will all retire with massive earnings. But in terms of consistent long-term wealth accumulation, baseball is king.

And the numbers back it up. Over the past two decades, we've watched MLB players sign a series of jaw-dropping megadeals: $252 million, $275 million, $330 million, $426.5 million, $500 million, $700 million, and now a record-setting $765 million. Thanks to a combination of talent, timing, and leverage, baseball's biggest stars have turned their careers into generational fortunes. Below, we've compiled the updated leaderboard of the highest career earnings in baseball history. It is an entirely different world from the list we published in 2014, which, frankly, looks quaint by today's standards.

The Rise of the Mega-Contract

It all started with Alex Rodriguez. In 2000, A-Rod signed a 10-year, $252 million deal with the Texas Rangers. At the time, it was the largest contract in the history of professional sports. Just seven years later, he shattered his own record by inking a new 10-year, $275 million deal with the Yankees. These contracts, combined with lucrative endorsement deals and playoff bonuses, helped Rodriguez retire with over $455 million in career earnings.

But baseball didn't stop there. The following decade saw a wave of billion-dollar spending sprees. The Phillies gave Bryce Harper $330 million. The Angels gave Mike Trout $426.5 million. The Padres gave Manny Machado $350 million. The Yankees gave Aaron Judge $360 million. And then came Shohei Ohtani, who signed a 10-year, $700 million contract with the Dodgers in December 2023, although most of the money is deferred until well into the 2040s.

That record didn't last long. In December 2024, Juan Soto signed a 15-year, $765 million contract with the New York Mets. It instantly set a new high-water mark not just for baseball, but for all professional sports globally. When you zoom out and look at career earnings, using guaranteed salaries only and excluding endorsements or bonuses, the game's biggest earners are already in a league of their own.

Top 25 Highest Career Earnings in MLB History

All figures reflect base MLB salary only. Endorsements, bonuses, and deferred interest are not included.

1. Alex Rodriguez – $455.2 million (1994 to 2016)
2. Justin Verlander – $419.2 million (2005 to present)
3. Miguel Cabrera – $400.4 million (2003 to 2023)
4. Max Scherzer – $366.6 million (2008 to present)
5. Albert Pujols – $346.5 million (2001 to 2022)
6. Zack Greinke – $338.5 million (2004 to present)
7. Stephen Strasburg – $320.5 million (2010 to present)
8. Mike Trout – $319.3 million (2011 to present)
9. Clayton Kershaw – $307.2 million (2008 to present)
10. David Price – $271.0 million (2008 to 2022)
11. Bryce Harper – $256.8 million (2012 to present)
12. Manny Machado – $253.5 million (2012 to present)
13. Robinson Canó – $248.7 million (2005 to 2022)
14. Aaron Judge – $236.0 million (2016 to present)
15. Gerrit Cole – $230.1 million (2013 to present)
16. Jon Lester – $198.0 million (2006 to 2021)
17. CC Sabathia – $193.0 million (2001 to 2019)
18. Chris Sale – $182.5 million (2010 to present)
19. Anthony Rendon – $180.0 million (2013 to present)
20. Jason Heyward – $179.5 million (2010 to present)
21. Joey Votto – $175.0 million (2007 to 2023)
22. Yu Darvish – $173.0 million (2012 to present)
23. Nolan Arenado – $170.0 million (2013 to present)
24. Carlos Correa – $168.0 million (2015 to present)
25. Troy Tulowitzki – $164.0 million (2006 to 2019)

Looking Ahead: The $500M, $700M, and $765M Club

There's a new class of players on deck poised to eclipse the current leaders. Shohei Ohtani's $700 million contract is technically the largest in history, though only $2 million per year will be paid during the contract term. Most of his earnings won't count toward his career total for decades. Juan Soto, on the other hand, is earning his $765 million in real time. If he plays through the full deal, he will end his career as the first baseball player to actually take home more than $700 million in guaranteed MLB salary.

And then there's Vladimir Guerrero Jr., who signed a 14-year, $500 million extension with the Blue Jays in 2025. If all goes according to plan, he could be the third member of this ultra-exclusive club.

One thing is clear. Baseball's financial ceiling is nowhere near its peak, and the next generation is already cashing in.

Read more: The Highest Career Earnings In Baseball History

Ray Ozzie is an American entrepreneur, software entrepreneur, and programmer who has a net worth of $650 million. Ray Ozzie is best known for developing Lotus Notes, serving as Chief Software Architect at Microsoft after Bill Gates, and playing a pivotal role in shaping the modern computing landscape. A visionary technologist with a deep understanding of collaboration and communication software, Ozzie has consistently been at the forefront of innovations that transformed how people work and share information. His work on Lotus Notes in the 1980s helped define groupware and enterprise communication. Decades later, his push for cloud computing and seamless integration across platforms influenced major shifts at Microsoft and beyond.

Ozzie's career spans several of the most influential software companies in history, and his quiet, thoughtful leadership style has earned him respect as a builder and strategist. Whether pioneering distributed computing in the early PC era or advocating for Microsoft's transition to the cloud, Ozzie's contributions have had a lasting impact on enterprise software and internet-based collaboration. Even after his formal roles at tech giants ended, he remained active through advisory roles and new ventures like Talko, continuing to shape the tools that enable communication in the digital age, and Blues Wireless, a company focused on simplifying Internet of Things (IoT) connectivity for real-world applications.

Early Life and Education

Raymond Ozzie was born on November 20, 1955, in Chicago, Illinois. He showed an early interest in computing and programming, eventually attending the University of Illinois at Urbana-Champaign, which housed the influential PLATO computer system. PLATO (Programmed Logic for Automatic Teaching Operations) introduced Ozzie to online collaboration and interactive computing, concepts that would influence his later work.

He graduated in 1979 with a degree in computer science and began his career in software development during a period of rapid innovation in personal and business computing.

Lotus Notes and Iris Associates

In the early 1980s, Ozzie worked at Data General and Software Arts, but his breakthrough came when he founded Iris Associates in 1984. There, he led the development of Lotus Notes, a pioneering software platform for messaging, collaboration, and document sharing within enterprises. It was one of the first major groupware products to integrate email, databases, and workflows across distributed networks.

Lotus Development Corporation, founded by Mitch Kapor, licensed and then acquired Iris Associates. Released in 1989, Lotus Notes became one of the most important enterprise software products of its time. It helped define a new category of business software and cemented Ozzie's reputation as a leading innovator in collaboration technology.

Role at Microsoft

After IBM acquired Lotus in 1995, Ozzie remained in the software industry but largely outside the spotlight until 2005, when Bill Gates recruited him to Microsoft as Chief Technical Officer, eventually elevating him to Chief Software Architect in 2006, the same title Gates held before stepping down from day-to-day operations.

At Microsoft, Ozzie was instrumental in shifting the company's focus from desktop-bound software to cloud-based services. His 2005 internal memo, titled "The Internet Services Disruption," argued that Microsoft was at risk of falling behind if it failed to embrace cloud computing and software as a service (SaaS). The memo helped spark initiatives like Windows Azure and Office 365, laying the foundation for Microsoft's future dominance in enterprise cloud services.

Ozzie also spearheaded the development of Live Mesh, an early effort at cloud synchronization and device interoperability. Although Live Mesh was eventually absorbed into other Microsoft services, it showcased Ozzie's forward-thinking approach to connected computing.

He stepped down as Chief Software Architect in 2010, concluding his formal tenure at Microsoft, though his strategic imprint on the company remained long after his departure.

Post-Microsoft Ventures

After leaving Microsoft, Ozzie launched Talko, a startup focused on rethinking voice communication for mobile teams. The app combined walkie-talkie-style messaging, conference calling, and collaboration tools. In 2015, Microsoft acquired Talko, integrating its technology into Skype and other communication products.

In 2019, Ozzie founded Blues Wireless, an Internet of Things (IoT) startup focused on simplifying the process of embedding wireless connectivity into physical products. The company's core product is the Notecard, a $49 plug-in module that provides instant cellular connectivity using built-in AT&T service. Developers can embed it into devices without requiring users to configure Wi-Fi or manage subscriptions.

Blues Wireless drew inspiration from Ozzie's experience with Safecast, a nonprofit that built open-source air quality and radiation monitors in the wake of the 2011 Fukushima disaster. That work highlighted the need for low-cost, easily deployable sensors that could share environmental data across networks.

Blues released its first consumer-facing product, the Airnote, in 2021. A solar-powered, cellular-connected air quality monitor, Airnote gathers environmental data and feeds it into Safecast's global public database. The project exemplifies Ozzie's long-standing commitment to enabling better information-sharing through technology, not just among people, but between machines and systems working in service of people.

Backed by investors including Sequoia Capital, AT&T, and Bill Gates, Blues Wireless continues to focus on making IoT connectivity more accessible and scalable, particularly for developers and enterprises looking to monitor real-world systems like energy infrastructure, logistics, and environmental health.

Personal Life & Real Estate

Not much is known about Ray's personal life other than that his wife is named Dawna. In 1995, Dawn and Ray paid $2.7 million for a historic 11,000-square-foot waterfront mansion in Manchester-by-the-Sea, Massachusetts. After acquiring the property, which dates to 1932, they performed a full restoration to its original glory. The restoration included re-adding the entire third floor and chimneys, which were removed decades earlier. Today, this property is worth at least $10 million, but perhaps much more.

Legacy and Influence

Ray Ozzie is widely recognized as one of the foundational figures in enterprise software. His work on Lotus Notes shaped decades of groupware and internal communication tools, while his leadership at Microsoft helped steer the company toward cloud computing at a time when such a pivot was critical for its long-term survival.

Though never as publicly visible as figures like Bill Gates or Steve Jobs, Ozzie's influence is deeply embedded in the infrastructure of modern business software. His emphasis on collaboration, synchronization, and distributed systems has informed the design of countless applications and platforms.

Read more: Ray Ozzie Net Worth

Bizzy Bone is an American rapper who has a net worth of $2 million. Bizzy Bone, born Bryon Anthony McCane, was raised in Columbus, Ohio. His early life was marked by severe trauma. At age four, he was abducted by his mother's boyfriend and held captive for over two years before being rescued. This experience, along with subsequent reports of abuse and molestation, deeply influenced his life and lyrical themes. At age 13, he moved to Cleveland to live with his sisters and their father. It was there he met Layzie Bone, Krayzie Bone, Wish Bone, and Flesh-n-Bone, forming the foundation of what would become Bone Thugs-n-Harmony.

The Peak of Bone Thugs' Success

Bizzy Bone emerged as the youngest and most emotionally raw member of Bone Thugs-n-Harmony. His high-pitched voice, rapid delivery, and spiritual lyrics became trademarks of the group's sound. During their peak in the mid-1990s, Bone Thugs released a string of hits including "Thuggish Ruggish Bone," "1st of tha Month," and the Grammy-winning "Tha Crossroads." Their albums "Creepin on ah Come Up" and "E. 1999 Eternal" went multi-platinum and established them as one of the most distinctive hip-hop acts of the decade.

Solo Career and Artistic Independence

Bizzy launched his solo career in 1998 with the release of "Heaven'z Movie," which debuted at #3 on the Billboard 200 and was later certified Gold. He followed this with a string of releases including "The Gift" (2001), which peaked at #2 on the Billboard Independent Albums chart, "Alpha and Omega" (2004), and "A Song for You" (2008). His solo work often explored spiritual themes, personal redemption, conspiracy theories, and the lingering effects of childhood trauma.

Despite limited promotion for many of his albums, Bizzy developed a loyal underground following. He continued to release independent projects such as "The Greatest Rapper Alive" and "Crossroads: 2010," and collaborated with Layzie Bone on the "Bone Brothers" series.

Television Appearance and Advocacy

In 2002, Bizzy appeared on "America's Most Wanted," hosted by John Walsh, where he spoke candidly about his abduction and abuse. He also performed a song titled "A.M.W." on the program, thanking Walsh and encouraging other survivors of child abuse to speak out. The episode was widely praised for its honesty and vulnerability, offering fans deeper insight into his personal struggles.

Legacy and Personal Life

Bizzy Bone has been an intermittent but essential figure in Bone Thugs reunions, joining his groupmates for tours, albums, and occasional flare-ups. Known for his unpredictability and emotional candor, he remains one of the most compelling and controversial members of the group. His contribution to melodic rap and vulnerability in hip-hop has influenced a generation of artists.

Read more: Bizzy Bone Net Worth

Brielle Biermann is an American reality television star, social media influencer, and entrepreneur who has a net worth of $500 thousand. Brielle Biermann is best known for her appearances on Bravo's "The Real Housewives of Atlanta" and its spinoff "Don't Be Tardy."

Brielle the daughter of Kim Zolciak and Daniel Toce. She and her sister, Ariana Biermann, were adopted by Kim's husband, Kroy Biermann.

Brielle grew up in front of the cameras and became a breakout personality thanks to her fashion-forward image, candid personality, and growing online presence. She later launched a successful career as an influencer, developing a loyal following through beauty partnerships, sponsored content, and public appearances. Brielle has remained a staple of Bravo culture while navigating public scrutiny, personal reinvention, and family turmoil, particularly surrounding her parents' highly publicized financial and legal troubles. Her journey reflects the challenges of fame at a young age and the struggle to define oneself outside of a reality TV legacy.

Early Life and Rise to Fame

Brielle was introduced to television audiences as a child when her mother joined the cast of "The Real Housewives of Atlanta." Her role expanded significantly with the launch of "Don't Be Tardy," where viewers watched her grow from a teenager into adulthood. As the show chronicled everything from prom to plastic surgery to her complicated relationship with her mother's husband, Kroy Biermann, Brielle became a key figure in Bravo's extended universe.

Off-screen, she built a brand around her image, capitalizing on her fame to pursue a career as a beauty influencer. With hundreds of thousands of followers across social media platforms, Brielle landed deals with makeup, fashion, and lifestyle brands, while also attracting attention for her striking resemblance to her mother and her evolving appearance.

Career and Business Ventures

Brielle has pursued various ventures tied to her public image, including launching a cosmetics line with Kim and participating in influencer campaigns. Her Instagram feed, often featuring designer outfits, luxury destinations, and behind-the-scenes glimpses into her family life, became central to her income. She has also expressed interest in entering the fashion and beauty space with her own brands, though several plans have stalled due to shifting family and financial dynamics.

Despite periodic criticism and public scrutiny, Brielle has remained open about cosmetic enhancements and life in the public eye, frequently defending her choices and speaking out about mental health, self-image, and growing up on camera.

Family, Relationships, and Public Scrutiny

As the daughter of Kim Zolciak and the adopted daughter of Kroy Biermann, Brielle has often found herself entangled in the drama of her parents' relationship. Kroy formally adopted Brielle after marrying Kim, and for many years, the family projected a united front on television. However, in recent years, Brielle has watched from the sidelines as Kim and Kroy's marriage deteriorated amid financial struggles, allegations of gambling, and foreclosure threats.

While she has stayed quieter than her sister Ariana about the fallout, Brielle has reportedly dealt with her own financial and emotional strain. Through it all, she has continued to show support for her siblings and mother, though her relationship with Kroy appears to have grown distant.

Life After "Don't Be Tardy"

As her family's Bravo shows ended and her parents' legal battles escalated, Brielle began to step back from the spotlight and refocus her public image. She remains a prominent figure on social media and has hinted at future television and business projects. Known for her loyalty to her inner circle and her desire to regain financial control, Brielle is entering a new phase marked by maturity, independence, and the search for long-term stability.

was born in Atlanta, Georgia in February 1997. She is the daughter of Kim Zolciak-Biermann and the adopted daughter of Kroy Biermann. Brielle Biermann starred on the reality TV series The Real Housewives of Atlanta from 2008 to 2009. From 2012 to 2017 she starred on the reality TV series Don't Be Tardy. Brielle Biermann has also appeared on episodes of the TV series Watch What Happens: Live, The Doctors, E! News Life, and Celebrity Page. She is also a model who walked for Michael Kuluva at New York Fashion Week in 2013. She has been romantically involved with minor league pitcher Michael Kopech of the Boston Red Sox. It was reported that Brielle Biermann earned $10 thousand for each episode of Don't Be Tardy for a total salary of $120 thousand.

Read more: Brielle Biermann Net Worth

Ariana Biermann is an American reality TV personality, influencer, and entrepreneur who has a net worth of $500 thousand. Ariana Biermann rose to fame on Bravo's "Don't Be Tardy," the family spinoff of "The Real Housewives of Atlanta." Ariana is the daughter of Kim Zolciak and Daniel Toce. She and her sister, Brielle Biermann, were adopted by Kim's husband, Kroy Biermann.

In June 2025, Ariana alleged that Kim and Kroy had spent the entirety of her early brand earnings. Her story is featured on the Bravo series "Next Gen NYC," which follows the lives of children of reality TV stars as they attempt to establish their own identities. Ariana's journey is defined by a search for independence, accountability, and personal reinvention after growing up in the spotlight.

Early Life and Influencer Career

Raised in Atlanta, Ariana became a familiar face on Bravo at a young age. Her breakout came through "Don't Be Tardy," where she appeared alongside her mother, stepfather Kroy Biermann, and sister Brielle. By the time she was in her mid-teens, Ariana had amassed a sizable social media following and began monetizing it through sponsored content and brand deals. She has described earning significant income through Instagram, doing multiple paid posts each week and securing partnerships based on her Bravo-driven visibility.

Allegations of Financial Mismanagement

Years after beginning her influencer career, Ariana claimed that she never received any of the money she had earned. On "Next Gen NYC," she alleged that Kim and Kroy spent her earnings without her knowledge or consent. She stated she had no idea how much money she made or how it was used, expressing frustration over the lack of transparency. The claims added to the public narrative surrounding her parents' legal and financial troubles, which included divorce filings, accusations of gambling losses, and the foreclosure of their Georgia home.

Personal Life and Relationship with Hudson McLeroy

Ariana has been in a long-term relationship with Hudson McLeroy, whom she met in high school. The two were raised in Atlanta and eventually relocated together to New York City to begin a new chapter. Hudson comes from a high-profile family as the son of Zach McLeroy, the billionaire founder of the Zaxby's restaurant chain. Hudson is an investor and artist, and he appears with Ariana on "Next Gen NYC." Their relationship has included extensive travel, shared milestones, and public displays of affection, with Ariana frequently describing Hudson as her best friend and soulmate. Despite family tension, the couple has remained a central part of each other's lives.

Legal Issues and Rebuilding

Ariana's path has not been without personal setbacks. She was arrested in a DUI case involving a minor accident and later entered a plea deal for reckless driving and possession of drug-related items. She received probation, a fine, and community service as part of her sentence. Rather than derail her ambitions, the incident became part of her broader story of growth and accountability.

Through her work on television and social media, Ariana continues to share her journey of recovery, self-discovery, and empowerment. She is focused on financial independence, emotional boundaries, and building a career defined by her own choices rather than her family legacy.

Read more: Ariana Biermann Net Worth

Krayzie Bone is an American rapper, producer, and entrepreneur who has a net worth of $4 million. Krayzie Bone, born Anthony Henderson, is an American rapper, producer, and entrepreneur known for his rapid-fire delivery, melodic hooks, and introspective lyricism. As a founding member of the Grammy Award-winning group Bone Thugs-n-Harmony, he helped define a new sound in 1990s hip-hop that fused harmony with street storytelling. In addition to his work with the group, Krayzie Bone has built a successful solo career and launched several ventures in business and philanthropy. His influence continues to resonate through multiple generations of hip-hop fans and artists.

Early Life and Formation of Bone Thugs-n-Harmony

Born and raised in Cleveland, Ohio, Krayzie Bone grew up in a religious household and gravitated toward music at an early age. In the early 1990s, he joined childhood friends Layzie Bone, Bizzy Bone, Wish Bone, and Flesh-n-Bone to form the group B.O.N.E. Enterpri$e. The group was later renamed Bone Thugs-n-Harmony after being discovered by N.W.A. rapper and Ruthless Records founder Eazy-E. Their breakthrough EP, "Creepin on ah Come Up," introduced their signature blend of melodic harmonies and rapid-fire rhymes. It was followed by the seminal full-length album "E. 1999 Eternal," which featured the chart-topping single "Tha Crossroads." The track won a Grammy Award and became a defining anthem of mid-90s rap.

Solo Career and Musical Success

In 1999, Krayzie Bone released his debut solo album, "Thug Mentality 1999," a double-disc project that included collaborations with Mariah Carey, Snoop Dogg, Fat Joe, Big Pun, and others. The album was certified platinum and demonstrated his ability to thrive outside of the group format. He followed it with "Thug on da Line," "Gemini: Good vs. Evil," and "Chasing the Devil: Temptation," among other releases. His solo work often explores themes of faith, survival, struggle, and social commentary.

One of his most high-profile collaborations came in 2006 when he appeared on Chamillionaire's hit single "Ridin'." The track reached No. 1 on the Billboard Hot 100 and earned the duo a Grammy Award for Best Rap Performance by a Duo or Group.

Entrepreneurship and Community Work

Krayzie Bone founded ThugLine Records, later renamed The Life Entertainment, as a platform to mentor and promote emerging artists. He also launched TL Apparel, a clothing line reflecting his personal brand and musical roots. In addition to his music industry ventures, he created the Spread the Love Foundation to promote music education and cultural equity in underrepresented communities.

In his hometown of Cleveland, he spearheaded the Harmony District initiative, a planned mixed-use development project in the Glenville neighborhood that includes residential and commercial space, intended to revitalize the local economy and create opportunities for Black entrepreneurs.

Personal Life and Health Challenges

Krayzie Bone is married to Andrea Henderson and has five children. In 2023, he was hospitalized with complications from sarcoidosis, a rare inflammatory disease he had battled privately for years. After emergency surgery and a prolonged recovery, he announced that he had regained his health and was grateful for the support he received during the ordeal.

Legacy and Recent Projects

Krayzie Bone remains an active force in hip-hop. In 2025, all five original members of Bone Thugs-n-Harmony reunited for the single "Aww S–t" and launched a national tour. He also began hosting a radio program titled "The Kray List," sharing music, stories, and interviews. With decades of influence behind him, Krayzie Bone is celebrated not only as a pioneer of melodic rap but also as an artist committed to community empowerment and creative evolution.

Read more: Krayzie Bone Net Worth

Gates also predicted that his current $160 billion net worth would be worth around $200 billion by 2045. So, in other words, Bill is committing to give away around $200 billion over the next twenty years.

But keep in mind- this future $200 billion is on top of the billions Bill has already given away or set aside for his foundation…

Where the First $100 Billion Went

Since launching the Bill & Melinda Gates Foundation in 2000, Gates has already donated roughly $60 billion of his personal wealth to the foundation. His longtime friend and fellow billionaire Warren Buffett has contributed an additional $43 billion, bringing the foundation's total endowment to well over $100 billion. That funding has already been deployed across more than 100 countries to tackle global challenges ranging from infectious diseases to extreme poverty and education inequality.

A major focus has been global health. The foundation has contributed billions toward eradicating diseases like malaria, tuberculosis, HIV/AIDS, and polio. It helped launch Gavi, the Vaccine Alliance, which has vaccinated more than 1 billion children since its inception and is credited with saving an estimated 17 million lives. The foundation has also provided extensive support to the Global Fund, the World Health Organization, and pandemic preparedness initiatives, including early COVID-19 vaccine development.

In the United States, Gates has poured billions into education reform, including public school systems, charter school networks, and education technology tools. The foundation committed $1.7 billion to support U.S. education in 2021 alone, including efforts to help schools recover from COVID-19-related learning loss. Another $200 million has been earmarked to improve public school curricula and access nationwide.

The Path Ahead

Looking ahead, Gates has made clear that Africa will be the primary focus of his final philanthropic push. In his 2025 speech, he outlined three long-term priorities: ending preventable deaths of mothers and children, eliminating deadly infectious diseases, and lifting millions out of poverty. He also encouraged African innovators to embrace artificial intelligence to revolutionize healthcare, noting that the continent skipped over traditional banking models and could now leapfrog legacy healthcare systems as well.

He cited examples like Rwanda, which has begun using AI-enabled ultrasound technology to identify high-risk pregnancies in remote areas. "Africa has a chance to build its next-generation health systems with AI already in the foundation," Gates said.

A Fortune Still Growing

The paradox of ultra-wealthy philanthropy is that even massive donations often fail to reduce a billionaire's net worth, because investment returns outpace their rate of giving. That's been true for Gates as well. In 2010, the year he co-founded the Giving Pledge, Gates had a net worth of $54 billion. By 2025, despite giving away tens of billions, his wealth had grown to $160 billion.

That dynamic is one reason why Gates is now aggressively accelerating his giving. He's made it clear he does not want to die with vast wealth still in his name. As he wrote in a recent blog post:

"People will say a lot of things about me when I die, but I am determined that 'he died rich' will not be one of them."

With $100 billion already donated or pledged, and another $200 billion potentially still to be given away over the next two decades, Bill Gates is on track to become the most generous philanthropist in history — and one whose giving may continue to shape the global landscape long after his foundation shuts its doors.

Read more: Bill Gates Pledges To Donate His Entire Remaining Fortune (Which He Predicts Will Grow To $200 Billion) To African-Focused Charities By 2045

While many artists scrambled to keep up with the evolving music industry, Chamillionaire embraced reinvention. He began making strategic investments in early-stage tech companies, long before it was trendy for celebrities to do so. In 2015, he became the first rapper to be named entrepreneur-in-residence at Upfront Ventures, one of Los Angeles's top venture capital firms. The title marked a significant shift: Chamillionaire was not just investing in startups, he was helping shape them from the inside out.

Over the past decade, Chamillionaire has built a second career that rivals, and in many ways surpasses, his success in music. He has invested in companies like Maker Studios, Ring, Lyft, and Cruise Automation, all of which were acquired for massive sums. He has also championed diversity in tech and launched pitch competitions to support underrepresented founders. It is a remarkable evolution for an artist once best known for a viral hit about avoiding the police. Chamillionaire did not just ride the wave of success; he learned how to build new ones.

Early Life and Musical Breakthrough

Chamillionaire was born Hakeem Seriki on November 28, 1979, in Houston, Texas. From the outset, he approached his music career with hustle and business savvy. Alongside Paul Wall, he convinced popular Houston DJ Michael "5000" Watts to let them freestyle on an intro to his show. Watts was so impressed that he included the freestyle on a mixtape, leading to increased visibility for the duo.

They formed The Color Changin' Click and released the independent album "Get Ya Mind Correct" in 2002. The project sold over 150,000 copies, a remarkable number for a local act with no major label support. Chamillionaire and Paul Wall quickly became key figures in Houston's influential mixtape circuit.

Mainstream Success

In 2005, Chamillionaire released his debut solo album, "The Sound of Revenge." It debuted at number 10 on the Billboard 200 and featured the hit singles "Turn It Up" and "Ridin'." The latter became a cultural phenomenon, earning platinum certification and wide acclaim. It was even parodied by "Weird Al" Yankovic in "White & Nerdy," bringing Chamillionaire a new level of pop recognition.

His second album, "Ultimate Victory," was released in 2007. It stood out in the rap landscape for its complete absence of profanity. While it did not match the chart success of his debut, it demonstrated a commitment to originality and message-driven content. Around this time, he also released multiple volumes of his "Mixtape Messiah" series and a trio of EPs titled "Ammunition," "Elevate," and "Reignfall."

Early Business Moves

Even during his rise in music, Chamillionaire showed signs of being a natural entrepreneur. In 2003, he invested in Fly Rydes, a Houston-based auto customization business. He partnered with Big Ernest and used his growing celebrity to drive awareness for the shop, tapping into Texas's vibrant car culture.

He also launched Chamillitary Entertainment in 2004, signing himself and a small roster of other artists, including Lil Ken and Troy Henry. The label released over 20 projects, providing a platform for independent music at a time when major labels were struggling to adapt to digital disruption.

His portfolio grew to include a modeling company called Masterpiece Mind Frame, created to help individuals develop structured plans for success. He also founded a luxury tour bus company, offering high-end features such as WiFi, surround sound, and full showers.

Tech Investments and the Maker Studios Payday

Chamillionaire's most notable business success came through tech. In 2009, he met venture capitalist Mark Suster and began attending events in the Silicon Valley and Los Angeles startup scenes. That same year, he became an early investor in Maker Studios, a digital video network built around YouTube creators. In 2014, Disney acquired Maker for an initial $500 million. After performance-based earn-outs, the final price landed at around $675 million, delivering a major win for early backers like Chamillionaire.

He also co-launched the Global Innovation Tournament at Stanford University as part of the school's Entrepreneurial Thought Leaders Series, encouraging students to develop creative business solutions to real-world problems.

Upfront Ventures and the VC World

In 2015, Chamillionaire formally joined Upfront Ventures as entrepreneur-in-residence. It was the first time a rapper had ever been given that title by a major venture capital firm. His role involved mentoring startup founders, advising on branding and marketing strategy, and helping evaluate investment opportunities in consumer tech.

Through this role and on his own, he invested in companies like Ring, which was acquired by Amazon in 2018 for over $1 billion, and Cruise Automation, which General Motors purchased in 2016 for a reported $1 billion. He also made early-stage investments in Lyft and Dropbox.

Supporting Minority Founders

Chamillionaire has used his platform to advocate for greater inclusion in tech and venture capital. In 2019, he launched a pitch competition for Black and female founders, offering a $25,000 investment of his own money. The competition expanded with support from figures like E-40 and Daymond John and became a recurring initiative aimed at closing the opportunity gap in startup funding.

He has spoken frequently about the challenges minority entrepreneurs face and the need for more diverse voices in the VC world. Rather than simply invest from the sidelines, he has positioned himself as a connector and mentor within the ecosystem.

Chamillionaire Today

Chamillionaire may no longer be in regular rotation on the radio, but his influence continues to grow in the business world. He remains active as an investor, advisor, and mentor, with a focus on consumer tech and emerging talent. His net worth is 50 chamillion dollars, the result of disciplined investing and entrepreneurial focus.

He once rapped, "I'm up earlier than a mother, chasing mine 'cause I'm a hustler." That line was not just a catchy lyric — it was a mission statement. Chamillionaire's transformation from chart-topping rapper to respected tech investor is one of the most successful and unlikely second acts in hip-hop history.

Read more: How Chamillionaire Went From Ridin' Dirty To Silicon Valley Power Player