Ranking the Yankees’ Top 5 Offseason Trades Since 2000

4. Didi Gregorius

In December of 2014, the Yankees made a three-way deal with the Cincinnati Reds and the Arizona Diamondbacks to acquire Didi Gregorius. His job was to replace a just-retired Derek Jeter at shortstop, a daunting task for any player. Gregorius took it pretty well and was solid in his prime, at least offensively. He registered 130+ hits in four of his five seasons with New York and provided stability at an important position during some rough years for the Bombers.

In his best two seasons, 2017 and 2018, the sweet-swinging lefty put up a combined 53 home runs, 173 RBI, an OPS of .812, and a brWAR of 9.4. He was also integral in October, driving in 16 runs in 28 career postseason games (all with New York). He also hit three memorable home runs in the 2017 postseason, cementing himself as one of the Yankees’ most clutch playoff performers of the 2010s.

3. Curtis Granderson

Dealt on December 8, 2009, from the Detroit Tigers in exchange for Austin Jackson and Phil Coke, Curtis Granderson had a fine four-year tenure with the Yankees. Over those four seasons, he accumulated a brWAR of 14.9, smacking 115 home runs, including 41 and 43 in 2011 and 2012, respectively. He was also voted to the All-Star team in both of those years, even finishing fourth in AL MVP voting in 2011.

Granderson wasn’t just a center fielder with a left-handed swing that was tailor-made for the short porch in right field; he was a fan favorite over his short but sweet tenure in the Bronx. While Coke and Jackson both spent some time in the big leagues, this was still a swindle of a deal for Cashman simply due to how productive Granderson was as a Yankee.

2. Giancarlo Stanton

This trade may not be a popular choice among Yankees fans looking at Giancarlo Stanton‘s egregious amount of time spent on the injured list in his career in the Bronx, but his impact on the team in the postseason is what gets him here. One could argue that without Stanton, the Yankees might not have even made the World Series this past fall. In 41 career postseason games, the slugger has hit 18 home runs and driven in 40 runs, complemented by a .994 OPS. That pace over 162 games? 71 home runs.

But that doesn’t mean he hasn’t been impactful in the regular season. He’s hit 162 home runs for New York in the regular season, though he’s only reached 100 RBI once since 2017. Even with the argument that Stanton hasn’t lived up to expectations in pinstripes, this was still a steal of a trade because of the return package sent to the Miami Marlins. Starlin Castro, the premier piece of the deal, put up two okay seasons with the Marlins before joining the Washington Nationals in 2020, and was out of the majors entirely after 2021. The other two prospects sent in the deal, Jorge Guzman and Jose Devers, have a combined career brWAR of -0.6.

1. Alex Rodríguez

There isn’t much to say about this one, perhaps one of the biggest blockbusters in recent memory. Even if Alex Rodríguez had chosen to leave the Yankees after the four remaining years left on the deal he signed with the Texas Rangers, this trade would still be worth it a thousand times over. From 2004 to 2007, A-Rod put up video game-esque numbers. Accumulating a brWAR of 30.9 at third base, he put up 173 homers and 513 RBI, along with a .303/.403/.573 slash line, winning two AL MVPs along the way.

Despite all the ensuing controversy that plagued Rodríguez’s career in New York, his impact on the roster was undeniable. Without him, they more than likely would not have won the 2009 World Series, and the entire look of the team for over a decade would be unrecognizable. Despite losing the beloved Alfonso Soriano, this was one of the best deals in MLB history simply due to the insane level of production that Rodríguez gave at the peak of his career.