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15 most expensive contracts in MLB history and how they turned out

By Michael Fisher

Mike Trout, Los Angeles Angels. (Photo by Jayne Kamin-Oncea/Getty Images)
Mike Trout, Los Angeles Angels. (Photo by Jayne Kamin-Oncea/Getty Images) /
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Gerrit Cole, New York Yankees, AL Cy Young Award power rankings
NEW YORK, NEW YORK – JUNE 14: Gerrit Cole #45 of the New York Yankees reacts after a double play to end the top of the sixth inning of the game against the Tampa Bay Rays at Yankee Stadium on June 14, 2022 in New York City. (Photo by Dustin Satloff/Getty Images) /

10. MLB contracts: Gerrit Cole, NYY – $324M/9 years

Gerrit Cole, the lone pitcher on our list of the most expensive MLB contracts, signed his current 9-year, $324M contract with the Yankees after losing the World Series with Houston in 2019.

The 32-year-old has impressed during his three seasons in pinstripes, being named to two All-Star teams and being mentioned for the Cy Young each season, finishing as high as second in voting in 2021.

The 6-foot-4 righty has so far done what the Yankees signed him for. He has stayed healthy and helped win games. He has a 36-19 record and led the majors with 257 strikeouts in 200.2 innings last season.

Being in New York, where it’s World Series or bust every year, Cole has mostly performed well in the postseason. He was solid in his first playoffs with the Yankees in 2020, pitching to a 2-0 record with a 2.95 ERA and 30 strikeouts in 18.1 innings.

After a rough two-inning start in the 2021 Wild Card, he bounced back in the 2022 postseason with a 2-1 record, a 2.95 ERA and 23 strikeouts in 18.1 innings.

But without winning a World Series, Cole will never cement his legacy with the Yankees and won’t be regarded as having lived up to the contract.

Cole can opt out following the 2024 season, so we might not even have a chance to see how this deal plays out.

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