The Best and Worst Trade of the Decade for the New York Yankees

After winning their 27th World Series championship in 2009, one would’ve thought that the ensuing decade would produce another ring for the New York Yankees; it didn’t. While they sported many great teams that won the American League East and went on a run in the AL playoffs, they never made it back to the Fall Classic.

With that said, they have a deep core around the diamond — which stems from crafty trades and player development — which has put them in contention in each of the last three seasons and will do so moving forward. On the other hand, not every trade has been a dandy for general manager Brian Cashman.

Over the next several weeks Baseball Essential will be doing a series on the best and worst trade every team in Major League Baseball has made over the last decade. Here is the best and worst trade the New York Yankees have made since 2010.

The Best Trade the Yankees Have Made Since 2010: Yankees acquire Gleyber Torres, Adam Warren, Billy McKinney, and Rashad Crawford from the Chicago Cubs for Aroldis Chapman (July 25, 2016)

The thinking from both sides in this trade was simple. The Cubs were contending for the World Series and looking to fill a void in the back end of their bullpen. Meanwhile, the Yankees were rebuilding/retooling and had a surplus of relievers, so they figured they’d get value for a soon-to-be free agent.

The Cubs won the World Series, and the Yankees got a top prospect, Gleyber Torres, so both teams got what they were looking for. So how is a trade that helped both teams the best trade of a 10-year span for one of them?

Torres made his big-league debut with the Yankees in 2018 and dazzled across 123 games, posting an .820 OPS and 122 OPS+ while totaling 24 home runs and 77 RBIs on a team that won 100 games. How did he follow it up? Oh, just by posting an .871 OPS and a 128 OPS+ while totaling 38 home runs and 90 RBIs. He also played both middle infield positions interchangeably, as the Yankees were hampered by injuries around the diamond all season.

Torres is a force to be reckoned with in the batter’s box. He swings a power bat, has gradually improved in his two seasons in the big leagues, and has flashed an ability to make highlight reel snags, though, Torres could become more consistent defensively. By the way, he’s 23.

A one-for-one swap of Chapman for Torres probably would’ve been enough for this trade to be the best of the decade for the Yankees. Except, that’s not where this story ends: the Yankees brought back Chapman in free agency on a five-year, $85 million deal.

Yes, they brought back the player they traded before the MLB trade deadline, meaning they essentially stole assets from the Cubs. It also doesn’t hurt that Chapman is one of the best backend relievers in the sport. Yes, he tends to get behind in counts and has Yankees fans holding their breath, but he works back into counts, logs strikeouts at a high rate, and is a force in the late innings.

Across his last 115 regular season appearances (2018-19) Chapman has recorded a 2.33 ERA, a 2.19 FIP, a 1.08 WHIP, and a 187 ERA+ while totaling 178 strikeouts. He also throws that 160 mph or whatever it is fastball; Chapman is as stellar as ever.

McKinney, Warren, and Crawford were either traded or haven’t reached the majors, but it doesn’t matter: the Yankees traded an impending free agent for a franchise player and then re-signed the player they traded. From the Yankees’ perspective, they robbed the Cubs at gunpoint, didn’t get caught, and committed the act again.

The Worst Trade the Yankees Have Made Since 2010: Yankees acquire Giancarlo Stanton from the Miami Marlins for Starlin Castro, Jorge Guzman, and Jose Devers (December 11, 2017)

When this deal went down no one could’ve envisioned it being a regretful transaction to the point where the Yankees would go to extremities to revoke it. Unfortunately for the Yankee faithful, everything that could’ve gone wrong with this trade has gone wrong.

The biggest issue with Stanton in Miami was his health, as he appeared in 150-plus games just twice in his eight years with the Marlins. Some felt that this would make his 13-year, $325 million deal difficult to justify. Even coming off winning the 2017 National League Most Valuable Player Award, one could argue that the Yankees didn’t need Stanton, as they had a well-versed outfield in Aaron Judge, Aaron Hicks, and Brett Gardner and weren’t by any means in need of power (the Yankees were first in MLB in home runs and second in runs in 2017).

With the Yankees at full force, Stanton is manager Aaron Boone‘s designated hitter. Defensively, Stanton has struggled. Part of that could derive from playing in a different ballpark or, more likely, him not having a set position, as he has played both corner outfield positions. Offensively, Stanton has been his potent self. The problem? Injuries.

He played through a hamstring injury in 2018 and missed most of last season due to multiple injuries; the Yankees still had one of the best offenses in baseball with Stanton appearing in just 18 regular season games. In February it came out that Stanton was expected to miss opening day due to a calf injury, meaning he would be off the field for at least a month.

The Yankees don’t need Stanton to have a functional offense. They have Judge, Torres, Gardner, DJ LeMahieu, Gary Sanchez, and Gio Urshela, which is an elite grouping. Stanton is the Yankees’ highest-paid position player.

Now, Guzman and Devers haven’t reached the big leagues, and Castro signed with the Washington Nationals this offseason, so it’s not as if the Marlins fleeced the Yankees in the players they swapped. That’s not the problem, here. The problem is the dollar signs that the Yankees are paying Stanton, a player who they don’t need and has been hampered by injuries.

His salary could’ve been allocated towards a top-end free agent starting pitcher last offseason such as Patrick Corbin or Dallas Keuchel. Imagine one of those two southpaws in a rotation with Gerrit Cole. Another option could’ve been the Yankees sign a second top starter this offseason. Heck, maybe they never need to sign Cole if they get Corbin or Keuchel; their rotation, the Yankees’ 2019 Achilles heel, would’ve been better in the wake of Luis Severino‘s absence.

When healthy, Stanton is one of the game’s most dangerous hitters. But that caveat is beginning to define his career, and he has become an expendable part of New York’s offense; they were in contention without him for 90 percent of last season. This trade isn’t holding back the Yankees’ contender status, rather Stanton’s $25 million average annual salary could’ve been utilized on an area of need. This trade is a blemish on Cashman’s resume.

Stay tuned to Baseball Essential over the next few weeks for more on the best and worst trades made by all 30 MLB clubs over the past 10 years.

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