30 biggest free agent contracts in New York Yankees history

11. DJ LeMahieu: Six Years, $90 Million

The jury's out on this one until the Yankees get a clean bill of health on LeMahieu's toe, but when he re-signed after the 2020 season, he went from one of the biggest bargains in Brian Cashman's recent history to a mid-tier question mark.

When LeMahieu's been healthy and available, he's delivered consistently and brought a much-needed gap-to-gap element to this home run happy team.

His season with the juiced ball in 2019 was ridiculously fruitful (26 bombs, .893 OPS, 136 OPS+), but his 2020 was somehow even stupider (1.011 OPS, 178 OPS+, .364 average in 50 games).

Don't let the uncertainty fool you, though; LeMahieu still registered 3.8 WAR last year despite being dragged down significantly during his final month of action, where he couldn't pivot or strike the ball with any pop.