New York Yankees: 3 Worst trades Brian Cashman made over five years

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The New York Yankees have made their share of good and bad trades over the past several years. Which of those were Brian Cashman’s worst?

Every general manager has had their share of very successful trades and very unsuccessful trades. Packages of prospects are often included in deals that may never see the major leagues. Some players make the successful transition to the Bronx. Others ultimately fail.

These are the three worst trades made by Brian Cashman over the last five years.

The Yankees acquire Brandon Drury

Following the 2017 season, Brian Cashman was facing an interesting situation. Chase Headley was being traded back to San Diego, leaving a hole at third base. The Yankees would address that hole on the eve of spring training, acquiring Brandon Drury from the Arizona Diamondbacks in a three-team trade.

The deal would cost the Yankees a pair of minor leaguers, with Nick Solak going to Arizona and Taylor Widener going to Tampa Bay.

The Yankees seemed like they were getting a bargain in the trade. Drury was coming off a solid season with the Diamondbacks, which saw him hit .267 with 13 home runs and 63 RBI. He was unable to find that success in the Bronx, though, after experiencing severe migraines early into the 2018 season before being placed on the injured list.

Drury’s replacement, Miguel Andujar, was able to find extreme success with the Yankees, especially at the plate. Defensively he may have been a step back from Drury, but he showed improvement in the field. At the plate, he produced enough that once Drury was healthy to return, he was optioned to Scranton/Wilkes-Barre.

Drury would only play in 18 games with the Yankees before being traded with Billy McKinney to the Blue Jays in exchange for J.A. Happ that July.

Adding Drury was very similar to the Didi Gregorius trade in 2014. Drury would be brought in as a young player with many years of team control to fill a hole in the infield. Drury just didn’t work out. Once Andujar took over in his remarkable rookie season, which saw him finish second in AL Rookie of the Year voting, it was over for Drury.

MINNEAPOLIS, MN – SEPTEMBER 11: Sonny Gray #55 of the New York Yankees delivers a pitch against the Minnesota Twins during the first inning of the game on September 11, 2018 at Target Field in Minneapolis, Minnesota. (Photo by Hannah Foslien/Getty Images) /

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.

NEW YORK, NEW YORK – OCTOBER 05: Giancarlo Stanton #27 of the New York Yankees hits a sacrifice fly to score Aaron Judge #99 in the third inning of game two of the American League Division Series at Yankee Stadium on October 05, 2019 in New York City. (Photo by Elsa/Getty Images) /

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.

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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.

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

The Yankees acquire Brandon Drury

The Yankees add Sonny Gray

The Yankees pick up Giancarlo Stanton

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