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Biggest Free Agent Contracts in MLB History

By Guest - 2023-12-27 20:39:31
Biggest Free Agent Contracts in MLB History

December 12, 1998, was the day in which Kevin Brown became the first free agent player in MLB history to sign a $100 deal when he agreed to a 7-year / $105 million deal with the Los Angeles Dodgers. Not only does that seem like ancient history, but the financial value of the contract pales in comparison to the deal that Shohei Ohtani just inked this past week. 

The question now becomes, who will be Major League Baseball’s first billion-dollar player?

1. Shohei Ohtani - Los Angeles Dodgers 10 years / $700 million

In just six years, the man known as “Showtime” has captured two American League MVP awards, three All-Star appearances, two Silver Slugger awards, and the Rookie of the Year. Oh, and in case you didn’t know, Shohei Ohtani has been one of the best pitchers and batters in all of MLB over the past three years. 

Obviously underpaid for his talents, it was inevitable that he would become the league’s (not to mention all team sports) highest-paid player of all time. Unfortunately for Los Angeles Angels fans, it would be their counterpart to the north who would sweep in and offer Ohtani the record-setting deal. 

2. Aaron Judge - New York Yankees 9 years / $360 million 

Imagine turning down $213.5 million. That’s exactly what Aaron Judge did when he turned down a $213.5 million extension from the Bronx Bombers prior to the start of the 2022 season. 

By betting on himself, Judge turned that deal into one worth $147 million more after capturing the American League MVP and breaking Yankees Hall of Famer Roger Marris’ AL home run record by belting 62 homers. Although the San Francisco Giants had been said to put a $400 million deal on the plate, Judge remained faithful to the team that drafted him in 2013. 

3. Bryce Harper - Philadelphia Phillies 13 years / $330 million

As the first overall selection in the 2010 MLB Draft, Bryce Harper was saddled with huge expectations by the Washington Nationals and their fans, and from 2011 through 2018 he lived up to them. 

A multiple-time All-Star and a National League MVP, Harper proved to be one of the best in the game. After seven seasons in the nation’s capital, Harper became the most sought-after free agent of 2019. While the Nationals presented the right fielder with multiple options, they paled in comparison to the rumored $45 million per year deal offered by the Los Angeles Dodgers and the massive deal he eventually agreed to with the Phillies. 

4. Corey Seager - Texas Rangers 10 years / $325 million

After earning a World Series Championship, World Series MVP, multiple All-Stars, and SilverSlugger Awards during his six seasons with the Los Angeles Dodgers, shortstop Corey Seager did it all again in 2023 as a member of the Texas Rangers. 

Just as UK Casinos offer deposit bonuses, as part of Seager’s decade-long deal, with the Rangers he received a signing bonus of $5 million. It wouldn't take long for Seager to prove his worth as he would earn back-to-back All-Star honors in his first two seasons in the Lone Star State. 

5. Gerrit Cole - New York Yankees 9 years / $324 million

It’s not that Gerrit Cole was a nobody when he was pitching for the Pittsburgh Pirates from 2013 through 2017 as he did earn an All-Star nod in 2015, it is that he hadn’t yet developed into one of the league’s most dominant pitchers just yet. 

Upon his arrival in Houston as part of a five-player deal, Cole evolved into an elite-level pitcher, one that would be rewarded with a massive deal offered by the Yankees during the 2019 offseason. Cole’s deal eclipsed the seven-year / $245 million deal signed by Washington Nationals pitcher Stephen Strasburg

6. Trea Turner - Philadelphia Phillies 11 years / $300 million

Trea Turner’s team success would come a few years before his individual recognition as one of the best shortstops in the game. Despite playing with a broken finger for most of the season, Turner would help the Washington Nationals to their first World Series title in 2019. 

After two seasons with the Los Angeles Dodgers, Turner would leave Tinseltown for a chance to help the Phillies return to the World Series after the team fell short of the championship in 2022. Armed with a massive contract, Turner posted his worst batting percentages since his rookie season. 

7. Manny Machado - San Diego Padres 10 years / $300 million

It was just a few years ago that Manny Machado’s $300 million contract was an earth-shattering deal. Playing the first seven years of his career with the Baltimore Orioles, the multi-talented infielder found himself traded to the Los Angeles Dodgers midway through the 2018 season. 

On February 21, 2019, Machado would ink the biggest free agent contract in team sports history when the four-time All-Star (he has earned two more since) signed with the San Diego Padres. Proving to be worth the money that the Padres invested in him, Machado finished among the top three in National League MVP voting in three of his first four seasons with the team. 

8. Xander Bogaerts - San Diego Padres 11 years / $280 million 

With two World Series rings, four All-Star appearances, and five Silver Slugger awards to his credit during his decade with the Boston Red Sox, Xander Bogaerts was one of the bigger names on the 2022 MLB free agent list. 

Undrafted as a teenager from San Nicolaas, Aruba, Bogaerts is the only player in MLB history to launch one out-of-the-park in four different countries, hitting homers in Canada, Mexico, the United Kingdom, and the United States. 

9 & 10. Alex Rodriguez - New York Yankees 10 years / $275 million

He may have been one of the greatest players in the history of the game, but the man known simply as “A-Rod” was also known for some questionable decision-making moments off the field. After playing his first seven seasons with the Seattle Mariners, a team he debuted for at the age of 18, Rodriguez would sign an incredible 10-year / $252 million free agent deal with the Texas Rangers. 

Three seasons later, Rodriguez would find himself traded to the Yankees. After just four years in New York, Rodriguez announced his intention to opt out of his contract, but just a few weeks later he would sign a second massive deal for $275 million. In 2009, Rodriguez would fill the one void that had been missing on his Hall-of-Fame resume, helping the Yankees win their 27th World Series title and his first.

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