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

The Yankees add Sonny Gray

Just like the Drury trade, this was a trade that did not involve the Yankees overpaying for a player initially. Sonny Gray was an All-Star pitcher who had several successful campaigns as a starter.

But his time in the Bronx was an absolute nightmare.

Gray was acquired at the trade deadline in 2017 for Dustin Fowler, James Kaprielian, and Jorge Mateo and was expected to be the number three starter for the Yankees as they made their push for the playoffs in what was supposed to be a rebuilding season.

In the first two months in the Bronx, Gray finished with a 4-7 record over 11 starts with a 3.72 ERA. It was not terrible, but it was not what the Yankees initially traded for, given his recent history of injuries.

The 2018 season was a year to forget for Gray as he struggled to an 11-9 record with a 4.90 ERA. His home/road splits were significant. On the road, hitters only hit .226 against Gray. At Yankee Stadium, that average skyrocketed to .318. His struggles forced the team to add Happ and Lance Lynn midseason.

Gray was traded to the Reds before the 2019 season, where he able to find success and was named an All-Star for the second time in his career.

In 2019, Gray ripped the Yankees for making him throw more sliders, which he was not comfortable throwing. Undoubtedly, this makes a pitcher less confident with himself and can affect his statistics.

At the time, the Gray trade seemed like a good risk to take. In the end, it did not work out at all.