Most Expensive Contract Extensions in MLB History
MLB’s largest contract extensions showcase the massive value teams place on their star players. These deals ensure superstars remain key pieces of their franchises while reshaping rosters and payrolls. As the sport evolves, these extensions set the benchmark for future negotiations and expectations.
Below are 15 of the most expensive contract extensions in MLB history.
Mookie Betts – Los Angeles Dodgers
Credit: flickr
$365 million over 12 years (2020) The Dodgers locked in Mookie Betts with a record-breaking extension after acquiring him from the Red Sox. Known for his exceptional all-around game, Betts has been a cornerstone in Los Angeles’ pursuit of championships. The deal includes a hefty signing bonus and ensures the team remains competitive with Betts leading the charge.
Mike Trout – Los Angeles Angels
Credit: Wikimedia Commons
$360 million over 10 years (2019) Mike Trout’s extension with the Angels elevated the total value of his contract to $426.5 million over 12 years. As one of MLB’s greatest players, Trout has consistently excelled at the plate and in the field. This historic deal cemented his legacy and underscored the Angels’ commitment to building around him.
Aaron Judge – New York Yankees
Credit: Wikimedia Commons
$360 million over 9 years (2022) Aaron Judge’s extension came after a record-setting season where he hit 62 home runs, breaking the American League single-season record. The Yankees recognized his power and leadership, making him the face of the franchise. Judge’s deal also made him the highest-paid position player by annual average value at the time.
Francisco Lindor – New York Mets
Credit: Wikimedia Commons
$341 million over 10 years (2021) Francisco Lindor’s extension followed a trade to the Mets, who made him their long-term centerpiece. His elite defense at shortstop, combined with his consistent offensive contributions, justified this massive deal. Lindor has become a leader for a Mets team determined to compete at the highest level.
Fernando Tatis Jr. – San Diego Padres
Credit: Wikimedia Commons
$340 million over 14 years (2021) Fernando Tatis Jr.’s contract extension signaled the Padres’ confidence in their young superstar. At just 22 years old, Tatis had already displayed incredible talent at the plate and in the field. The deal also highlighted a trend toward locking up young talent early to secure their prime years.
Bryce Harper – Philadelphia Phillies
Credit: flickr
$330 million over 13 years (2019) The Phillies made a long-term commitment to Bryce Harper with this franchise-altering deal. Known for his power and ability to get on base, Harper became the team’s focal point. The contract structure includes no opt-outs, emphasizing Harper’s desire to remain with Philadelphia and lead them to sustained success.
Corey Seager – Texas Rangers
Credit: Wikimedia Commons
$325 million over 10 years (2021) The Rangers made a bold statement by signing Corey Seager during their aggressive rebuild. His ability to hit for both power and average, coupled with his postseason success, made him a prized addition. Seager’s leadership and consistency have helped Texas return to playoff contention.
Giancarlo Stanton – Miami Marlins
Credit: Wikimedia Commons
$325 million over 13 years (2014) At the time, Giancarlo Stanton’s extension with the Marlins was the largest contract in sports history. His prodigious power and MVP-caliber performances defined his tenure in Miami. Although Stanton was later traded to the Yankees, his contract marked a turning point in MLB’s era of mega-deals.
Manny Machado – San Diego Padres
Credit: Wikimedia Commons
$300 million over 10 years (2019) Manny Machado’s extension with the Padres solidified their commitment to building a championship-caliber roster. A dynamic third baseman with a powerful bat, Machado’s deal reflected his value as both a player and leader. His presence, alongside other stars, has elevated the Padres’ status as perennial contenders.
Nolan Arenado – Colorado Rockies
Credit: Wikimedia Commons
$260 million over 8 years (2019) Nolan Arenado’s extension was a testament to his incredible consistency at third base. Renowned for his elite defense and offensive production, Arenado became the face of the Rockies franchise. Although he was later traded to the Cardinals, this deal highlighted his standing as one of the league’s best players.
Alex Rodriguez – Texas Rangers
Credit: Wikimedia Commons
$252 million over 10 years (2001) Alex Rodriguez’s groundbreaking deal with the Rangers redefined MLB contracts. At the time, it was the largest contract in sports history and showcased his unparalleled talent as a shortstop. Although the Rangers struggled during his tenure, A-Rod’s deal remains one of the most iconic in baseball history.
Trea Turner – Philadelphia Phillies
Credit: Wikimedia Commons
$300 million over 11 years (2022) Trea Turner’s extension came after his rise as one of MLB’s top shortstops. Known for his speed, power, and defensive prowess, Turner became a cornerstone of the Phillies’ championship aspirations. His ability to deliver in high-pressure situations has made him a critical part of their long-term plans.
Xander Bogaerts – San Diego Padres
Credit: Wikimedia Commons
$280 million over 11 years (2022) Xander Bogaerts joined the Padres as part of their ambitious spending spree. His consistent offensive production, coupled with his leadership qualities, made him a perfect fit for a team chasing championship glory. The deal also underscored the escalating market value for elite shortstops.
Gerrit Cole – New York Yankees
Credit: Wikimedia Commons
$324 million over 9 years (2019) Gerrit Cole’s extension made him the highest-paid pitcher in MLB history. Known for his dominance on the mound and ability to perform in big games, Cole has anchored the Yankees’ rotation since signing. The deal highlights the value of top-tier pitching in today’s game.
Stephen Strasburg – Washington Nationals
Credit: Wikimedia Commons
$245 million over 7 years (2019) After leading the Nationals to their first World Series title and earning MVP honors, Stephen Strasburg signed this lucrative extension. His postseason brilliance and electric pitching secured his legacy in Washington. The contract reflected the team’s commitment to retaining their championship core.