Yankees: 3 worst trades Brian Cashman has made in the last five years

The Yankees pick up Giancarlo Stanton

Brian Cashman knew he had to take a risk after losing to the Astros in seven games in the 2017 ALCS. That risk would include taking on Giancarlo Stanton, whose biggest concern was his contract.

The Marlins were unloading multiple players that offseason, trading Marcell Ozuna and Christian Yelich in separate deals. The Yankees were able to add Stanton (and cash) for Starlin Castro and a pair of minor leaguers.

Stanton had a good 2018 season, which saw him hit 38 home runs with 100 RBI in 158 games. The 2019 season did not fare well for Stanton, as he struggled with injuries and only had 59 at-bats during the regular season.

It is not how badly Stanton has played during his time in New York that has been the problem. The problem is the lucrative contract he signed after the 2014 season. The 13-year, $325 million extension was the biggest contract given to any athlete at that time. The deal runs through the 2027 season with a club option for the 2028 season.

Stanton is locked into the Yankees payroll for many years to come, as no other team will be willing to take on his contract.

For what Stanton can potentially do on the field, the trade was fine. Stanton can be a very productive ballplayer when he is healthy. Cashman figured that the positives would outweigh the contract. So far it hasn’t.