Yankees: Riskiest Contracts on the Payroll Right Now

Yankees GM Brian Cashman has a lot of money tied up right now in risky deals.

We’ve seen a number of bad contracts on the Yankees’ payroll over the years, with Jacoby Ellsbury’s deal still making us twitch after six years. But fans might overlook the fact that New York has some current (and still active) risky deals, despite the team performing admirably over the last three seasons and adding Gerrit Cole a few months back.

General manager Brian Cashman has used the organization’s deep pockets over the years, but he’s been forced to scale back as of late (with the exception of Cole and one other player on this list), leaving a lot of his work to be done on the trade market. He’s done a great job on that front, but these three contracts should still concern Yankee fans to an extent.

Yankees’ riskiest contracts: Aaron Hicks

Can Aaron Hicks justify his seven-year contract with the New York Yankees?

Speaking of Cashman’s wizardry on the trade market, he acquired Aaron Hicks from the Minnesota Twins in exchange for catcher John Ryan Murphy in November of 2015. While Hicks has shown flashes of greatness with his defense and powerful bat, he’s still slashing just .242/.341/.433 in the Bronx and has dealt with numerous injuries, including an elbow issue that required Tommy John surgery this offseason. He played in just 88 games back in 2017, 59 contests this past year, and will likely miss part of 2020 (whenever baseball returns) in his recovery from TJ, which makes the seven-year, $70 million extension he signed before the 2019 season even more puzzling. Hicks is tied to New York through 2025 (his age-35 season). It could certainly end up working out, but giving him an average of $10 million per season for that long when he’s been unable to stay on the field and be consistent is the definition of risky.

Yankees’ riskiest contracts: Giancarlo Stanton

Giancarlo Stanton can’t help but weigh down the Yankees’ payroll.

No, the Yankees didn’t have to give up much in the trade for Giancarlo Stanton — prospects Jorge Guzman and Jose Devers, along with Starlin Castro, went to Miami — but they did acquire (at the time) the largest contract in North American sports. The Marlins signed Stanton to a 13-year, $325 million deal before the 2015 season, which has since been eclipsed by Bryce Harper ($330 million) and Mike Trout ($426.5 million). Stanton will be making anywhere between $25 million and $32 million per year throughout the life of his deal, tying him to New York through the 2027 season (and he’s got a $10 million buyout or $25 million team option for 2028). He has an opt-out clause coming up, but it’d be senseless for him to exercise it. That means Stanton will be in the Bronx through his age-37 season, and that can’t have fans feeling comfortable, given his injury history. Before coming to the Yankees, he dealt with knee issues, which kept him out of significant portions of four seasons. While his inaugural year with New York was tremendous, he was limited to just 23 total games in 2019, and started off the 2020 season battling injuries that prevented him from participating in spring training. In short, nobody has any idea how this deal is going to pan out.