When a superstar athlete in MLB signs a mega-deal, the numbers are usually met with shock. It’s important to remember one thing, though. Unlike other leagues, every penny of that contract is guaranteed. When Mike Trout signed with the Anaheim Angels for $426.5 million at 27 years old, he was set for life. Trout isn’t the only superstar to sign for hundreds of millions, however. These are all the MLB stars who have signed on the dotted line for at least $200 million.
Mike Trout – $426.5 Million
Mike Trout was already in the middle of one mega contract in 2019 when the Anaheim Angels offered him 10 more years and $360 million more dollars. The extension meant that the total length of Trout’s 12-year deal with the Halos was worth $426.5 million.
Is Trout worth all that money? In the world of baseball, he absolutely is. Still in his prime, the Angels made sure to lock up their valuable three-time AL Most Valuable Player.
Mookie Betts – $392 Million
In July 2020, Boston Red Sox fans looked on in shock as the Los Angeles Dodgers inked superstar outfielder Mookie Betts to a 12-year contract extension worth $365 million. Betts, who was traded to LA from Boston in the offseason, gets the deal added to his current contract.
Since Betts is set to earn $27 million in 2020, the total length and value of his contract is 13-years and $392 million, the second richest contract in MLB history. Not bad for a 27-year-old former MVP.
Bryce Harper – $330 MIllion
Not many superstars in MLB hit the free-agent market at 26 years old, but NL MVP Bryce Harper did in 2019. The former Washington National wanted to set the market price and sign the biggest contract of all time.
At the end of his free-agent road, his choices were to sign with the Phillies or the Giants. He chose Philadelphia, stating it was where he and his wife wanted to raise their kids. Before Trout signed his mega-extension, Harper’s 13-year, $330 million contract set the MLB bar.
Giancarlo Stanton – $325 Million
The first truly regrettable contract on this list belongs to Giancarlo Stanton. A former NL MVP and one of the most powerful hitters of his generation, the big man’s talent isn’t the problem. It’s his ability to stay healthy.
As a Marlin, Stanton lost a lot of games due to injuries. When the Yankees traded for him and his current contract, they must have believed they could manage the wear-and-tear on his body. In 2019, his second in the Bronx, Stanton only appeared in 18 games.
Gerrit Cole – $324 Million
The hottest player on the free-agent market after the 2019 season ended was Gerrit Cole. The bidding war that followed turned him into the highest-paid pitcher of all-time. And what was the winning offer? A $324 million contract from the Yankees with an annual average salary of $36 million.
Cole began his career in 2013 with the Pittsburgh Pirates, where he became an instant star. After a few seasons, the struggling team flipped him to the Houston Astros where he played in his first World Series.
Manny Machado – $300 Million
The San Diego Padres came out of the shadows in 2018 to offer Manny Machado a $300 million contract. Sports analysts had ticketed the power-hitting infielder to go to the high-spending Los Angeles Dodgers when the deal with the more frugal Southern California team was announced.
The ten-year pact was the largest ever given by the Padres, and it would be fair to wonder how long he’ll stay in brown in yellow if the team doesn’t start winning soon.
Alex Rodriguez – $275 Million
This is just the first of two appearances for Alex Rodriguez on this list. After opting out of one $200+ million contract, he signed a monster $275 million deal to stay with the Yankees in 2007. It was hailed at the time as a bargain but ended up being filled with controversy.
In the following years, Rodriguez’s career became marred by steroid allegations and his connection to Biogenesis. In 2016 he retired, and while he should get into the Hall of Fame, his past transgressions have made his chances seem murky at best.
Nolan Arenado – $260 Million
The Colorado Rockies knew they had a superstar in Nolan Arenado when they added $234 million to his current contract. The total $260 million deal assured the slugger would be staying in the Mile High City for a long time.
As of 2019, however, the marriage between the player and the team has not looked good. Arenado openly expressed frustration that the Rockies were not adding more talent to try and win, leading Colorado to explore trading him. As of this writing, no trade has been made.
Alex Rodriguez – $252 Million
In 2000, Alex Rodriguez signed what, by many, is considered the first mega-deal in MLB history. Choosing to go from Seattle to Texas, Rodriguez inked a 10-year, $252 million deal. Unfortunately, the deal proved too rich for the Rangers, who traded him to the Yankees just a few years later.
Of course, with the Yankees, Rodriguez didn’t play through his entire contract. Seven years into the deal he opted out to sign for more money in a contract that has already been discussed on this list.
Miguel Cabrera – $248 Million
Miguel Cabrera was an aging superstar two years away from free agency when the Detroit Tigers handed him a $248 million contract extension. The move came on the heels of the team losing another superstar in Prince Fielder.
Unfortunately, just as soon as Cabrera signed on the dotted line, his performance on the field cratered. His bat lost its power and his ability to stay healthy was lost. All in all, this was one of the worst big-money deals ever handed out by a team.
Stephen Strasburg – $245 Million
Stephen Strasburg was a key player in the Washington Nationals’ 2019 rise to become World Series champions. He was magical for the team that struggled at the beginning of the year only to get hot just as the postseason arrived.
Strasburg was rewarded by the team with a $245 million contract in the offseason. Now 31 years old, it is likely that the deal will mean Strasburg plays his entire career for one team.
Anthony Rendon – $245 Million
Anthony Rendon became an NL MVP candidate in 2019 after leading the league in runs batted in while swatting 34 homers. A late bloomer in his career, Rendon hit the free-agent market at 29 years old and cashed in with the Anaheim Angels.
The Southern California team inked Rendon to a seven-year, $245 million contract. The deal came just a few days after Strasburg’s deal — a deal that closed the door on Rendon returning to Washington.
Albert Pujols – $240 Million
Albert Pujols was 32 years old when he signed his monster $240 million deal with the Anaheim Angels. The Halos thought they were getting an ageless star. What they actually got was a player with a weight problem and a declining skill set.
Since joining Anaheim, Pujols’ batting average has dropped .50 points, and while he can still knock in 100 runs a season, he can’t run the bases like he used to. The good news is that Pujos’ contract ends after the 2021 season.
Robinson Cano – $240 Million
Robinson Cano is the rare case where the New York Yankees didn’t get their man. Cano started his career with the Yankees in 2005, and after the 2013 season, the team hoped to retain him and offered him a seven-year, $175 million contract.
Cano held out for more money, and eventually signed with the Seattle Mariners for ten years and $240 million. Seattle held on to Cano until 2019 when they successfully traded the back end of his contract to the New York Mets.
Joey Votto – $225 Million
The Cincinnati Reds rarely hand out big money contracts, so when they inked franchise star Joey Votto to his $225 million deal it came as a surprise. Votto, of course, has been worth every penny.
Now 36 years old, Votto isn’t the hitter he used to be, but that doesn’t seem to bother Reds’ fans. His contract will officially end in 2023, although there is an option for 2024 if he has a surprise late-career resurgence.
David Price – $217 Million
David Price has moved around a lot during his MLB career. He came up with the Tampa Bay Rays, was traded to the Detroit Tigers, and then was traded to the Toronto Blue Jays. And all of this came before he signed his $217 million contract with the Boston Red Sox in 2016.
It didn’t take long, however, for the Red Sox to have buyer’s remorse. Looking to offload his albatross of a contract, the team traded him, along with superstar Mookie Betts, to the Los Angeles Dodgers.
Clayton Kershaw – $215 Million
In no way, shape, or form do the Los Angeles Dodgers regret giving NL MVP and three-time Cy Young Award winner Clayton Kershaw his $215 million deal. In retrospect, it even looks like a bargain!
In more recent years, Kershaw has been hampered by back injuries, and his playoff inefficiencies have become a thing of legend, but still, it’s hard to deny that he has been worth every dollar for the perennial World Series contender.
Christian Yelich – $215 Million
The most recent member of the $200 million club is Christian Yelich. A standout player for the Miami Marlins, when the team turned their attention toward rebuilding, he was traded to the Milwaukee Brewers.
In Milwaukee, Yelich became a superstar and was named the National League’s Most Valuable Player in 2018. Two years later, on March 6, 2020, the Brewers awarded Yelich with a $215 million contract, making him the unquestioned face of the franchise.
Prince Fielder – $214 Million
A mere two years after signing Prince Fielder to a $214 million contract, the Detroit Tigers traded him and $30 million dollars to the Texas Rangers for Ian Kinsler. The move worked out for Detroit, but not for Texas.
Fielder played for the Rangers for three seasons but spent most of his time on the injured list. At the end of the 2016 season, at just 32 years old, Fielder was forced to retire with a back injury.
Max Scherzer – $210 Million
After a five-year career in Detroit, Max Scherzer took his talents to Washington D.C. and signed a $210 million contract in 2015. The deal made him the highest-paid player on the team at the time.
Scherzer has been more than worth the money. Since joining the Nationals, he has thrown multiple no-hitters, won two Cy Young Awards, and helped the team win its first-ever World Series championship.
Zack Greinke – $206.5 Million
The Arizona Diamondback sent shockwaves through the baseball world when they signed Zack Greinke to a $206.5 million contract in 2015. The deal sent a message that the team was ready to compete for a World Series. Unfortunately, the move may have been premature.
On July 31st, 2019, the team traded Greinke and his big-money deal to the Houston Astros, who rode the big-armed pitcher to their second World Series appearance in three seasons.