Will The Yankees Regret Another Long-Term Contract?

With the recent signing of Gerrit Cole to a massive nine-year contract, will the Yankees have another long-term contract they will soon regret?

On December 18, 2019 the Yankees signed Gerrit Cole to the fourth largest contract in baseball history. It lasts nine years and is worth a Yankee record $324 million. After a little over a week to digest the deal, I’m beginning to have doubts about my initial take.

Cole earns the highest average salary in baseball history at $36 million dollars per year, surpassing Mike Trout’s $35.5 million. At the time of Trout’s contract, he had already won the Rookie of the Year, six silver sluggers and two MVP’s while also finishing second four times. He validated the record contract by immediately winning his third MVP in 2019.

Yes, the 6’4’’ righty has been a top three pitcher over the past two years. Yes, he has led baseball in strikeouts over that period. However that doesn’t take away from the fact that two seasons is a very small sample size. The last time the Yankees had a knee jerk reaction to a hurler’s sudden stardom came nearly 15 years to the day of the Cole signing.

On December 20, 2004 the Yankees inked Carl Pavano to a four-year deal worth $39.5 million following a career season with the Marlins. Pavano would go on to win just nine games, losing eight while posting a 5.00 ERA during three seasons in the Bronx.

No position player outside of Trout is worth $324 million, let alone a pitcher who to this point is just a three-time all-star and 2019 Cy Young finalist. Worse yet, Cole will be playing in just 20 percent of the team’s games over the next nine seasons. And that’s only if he can stay healthy, something few starting pitchers are able to accomplish today.

As a fan I could honestly care less about Hal’s money. While the signing has risk from an investment standpoint, I am more concerned with its impact on the Yankees’ ability to extend their homegrown talent – Judge, Sánchez, Torres and Severino. And with Cole’s contract on the books for the next nine seasons, it is going to be extremely challenging to find cap space for all four, especially if they continue to perform at such high levels.

In modern baseball successful long-term deals rarely work out. The success rate is even lower for pitchers. With the exception of Max Scherzer and our old friend CC Sabathia, six of the eight largest pitching deals have failed to provide any significant return on investment. And the jury is very much still out on the two biggest deals.

Tied for number ten we have Jon Lester and our very own Masahiro Tanaka coming in at six and seven years respectively, each totaling $155 million. Lester has been incredibly inconsistent with the Cubs over the first five seasons. With the exception of his 2016 (19-4, 2.44 ERA) and 2018 (18-6, 3.32) campaigns the 35-year-old southpaw has been incredibly mediocre, posting a combined 37-30 record with a 4.01 ERA. Masahiro Tanaka has averaged just 12.5 wins and 7 losses with a 3.75 ERA during his six years in pinstripes.

Coming in just ahead of CC Sabathia, we have Felix Hernandez at eighth. King Felix signed a seven year $175 million deal with Seattle back in 2013 and over those seven seasons he went a combined 84-60 with a 4.14 ERA, never even sniffing the playoffs.

At seventh we have the surefire Hall of Famer Justin Verlander. The veteran inked a seven year $180 million contract with the Tigers in 2013. With only 49 wins, 41 losses and cumulative 3.65 ERA during the first four years of the deal he was traded in 2017 and found a new lease on life in Houston.

The sixth largest pitching contract of all-time belongs to the silent assassin, Zack Grienke. After signing a six-year $206.5 million contract with Arizona in 2016, Zack would last just three and a half seasons before the team decided to clear cap space prior to the 2019 season trading away Paul Goldschmidt to the Cardinals and Grienke to the Astros. He would go on to pitch to a 55-29 record with a 3.40 ERA during his time in the desert. But with the early exit, the D-Backs are now paying 53 of the remaining 77 million dollars for him to pitch for the Astros.

Sliding in at fourth ahead of Scherzer we have Clayton Kershaw who agreed to a seven year $215 million deal in 2016. Despite being arguably the greatest regular season pitcher to ever toe the slab, the southpaw hasn’t just been bad in the postseason; he’s been a liability. In 32 appearances in October, Kershaw is 9-11 with a 4.43 ERA including his most recent failure in game five of last years NLCS giving up back-to-back homers to Anthony Rendon and Juan Soto, virtually handing Washington their first World Series appearance.

The third richest pitcher ever, David Price signed a seven year $217 million contract with the Boston Red Sox back in 2016. Since joining the Sox, Price’s career ERA has increased from 3.09 to 3.84. He also missed much of the 2017 and 2019 seasons with lingering injuries. When healthy, he has shown flashes of greatness in Boston, but that’s only about 50 percent of the time and certainly not worth anywhere near $200 million.

Stephen Strasburg and Cole top the list as the two biggest pitching contracts in baseball history. My view on the Cole contract has already been documented. As for Strasburg, the 2019 World Series MVP certainly earned his payday (seven years, $245 million) pitching to a 1.99 ERA over 36.1 postseason innings including five of the teams 12 playoff victories. Of course, there is still a ton of risk, but I’m sure Mike Rizzo feels much more comfortable with his investment than Brian Cashman right about now.

Giving a pitcher a long-term deal is a roll of the dice. And given that Cole’s contract is two years longer than any pitcher in baseball history, it’s inevitable that he will suffer injury or setback over the next nine years. Will the acquisition of Cole cost the Yankees the second coming of the Core Four? Only time will tell.

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