5 worst contracts in modern New York Yankees history

4. DJ LeMahieu

One of my favorite players! The Yankees’ Team MVP from 2019-2020! Someone who was clearly hurt by the disappearance of the rocket balls in 2021, and can theoretically remain a valuable player as he ages!

Still, it’s hard not to put a player on this list who signed a six-year, $90 million contract, but will apparently be converted to a roving utility infielder and lose his starting job in Year 2.

Now that Rob Manfred has admitted he’s been using (at least!) two different baseballs the past several years in both showcase events and “boring” games (which the Yankees rarely play), LeMahieu’s 2021 regression is a bit more explainable. Factor in the core muscle surgery he had to repair a sports hernia that knocked him out of the Wild Card Game, and you’ve got one reason for hope that things can change for the duration of the deal, even if Manfred doesn’t touch the baseballs ever again.

That said, LeMahieu, now 33, is coming off a season where he ranked 12th percentile in barrel percentage and in the 32nd percentile in expected slugging. He still hit the ball moderately hard, but he hit it on the ground far too often, resulting in an overload of double plays even when he was at his theoretical best.

You can’t rule out his contributions moving forward, but when Hal Steinbrenner points to LeMahieu’s deal as a retrospective reason he stayed out of the shortstop market this offseason, all while picking him up and moving him all around the diamond (first base?) in a desperate attempt to justify the investment, you can’t help but trend the contract towards the “mistake” column.