Top 5 richest Yankees contracts in history: Record-breaking MLB deals, and massive contracts revealed

The New York Yankees have always spent big to win big. Over the years, the team has handed out some of the largest contracts in MLB history. These deals show how serious the Yankees are about star power and championships. From home run kings to ace pitchers, here are the richest Yankees contracts ever.

Aaron Judge’s $360 million deal changed Yankees history

Aaron Judge signed a nine-year, $360 million contract with the Yankees in December 2022. The deal runs from 2023 through 2031 and pays him $40 million per year. That made it the biggest contract in Yankees history. Judge earned it after breaking the American League home run record in 2022. Aaron Judge continues to serve as Yankees captain and remains the face of the franchise heading into the 2025 season.

Gerrit Cole’s $324 million contract leads Yankees pitching deals

Gerrit Cole agreed to a nine-year, $324 million contract in December 2019. At the time, it was the largest deal ever for a pitcher. The contract runs through 2028. Cole won the Cy Young Award in 2023. In 2024, he dealt with an elbow injury but returned later in the season, and the Yankees have confirmed he remains their top starter going forward.

Giancarlo Stanton’s $325 million massive contract came through a trade

Giancarlo Stanton joined the Yankees in 2017 after a trade with the Miami Marlins. His original deal was 13 years, $325 million. While Miami pays part of it, the Yankees are still responsible for more than $300 million overall. Stanton remains under contract through 2027. He continues to be known for his raw power, even as injuries have limited his playing time in recent seasons.

Alex Rodriguez received two record-breaking Yankees contracts

Alex Rodriguez signed two huge contracts with the Yankees. The first was 10 years for $252 million. The second was 10 years for $275 million, signed in 2007. By the time he retired in 2017, the Yankees had paid him over $300 million. Alex Rodriguez played a key role in the 2009 World Series win, making these deals historic despite later controversies.

Carlos Rodón’s $162 million contract remains important for the Yankees

Carlos Rodon inked six years, $162 million in 2022. That’s $27 million a year mostly till 2028. Right after Judge’s deal, Yanks grabbed this ace starter. Rodon brings high strikeouts but some injury bumps. Still rounds out the top five nicely.Also Read: Freddie Freeman And Chelsea Freeman Combined Net Worth In 2025: MLB Star Earnings, Business Work, And Their Life Together