Ranking the 10 Best Yankees Trades in MLB's Modern Era
For the 34th time in 34 seasons, the New York Yankees will close out 2026 with a winning record. Any team that can do this must be good at doing business.
So, come along with us as we look back at the 10 best trades the Yankees have made in their modern era.
Though the streak of winning seasons started in 1993, we pushed the start line back to 1990 for the sake of including one trade in particular. Overall, the idea was to look for deals that have had a lasting impact on the Yankees, regardless of whether they "won" the deal in a traditional sense.
After beginning with some honorable mentions, we'll count down from No. 10 to No. 1.
Honorable Mentions
1 of 11
The Scott Brosius Trade
Date: November 18, 1997
The Trade: New York Yankees get 3B Scott Brosius (as PTBNL); Oakland Athletics get LHP Kenny Rogers, cash
Brosius came out of nowhere in 1998 to become an All-Star and the eventual World Series MVP, so this trade gets major nostalgia points just on that account. It was mostly downhill from there, but he'll always have that epic tying home run in Game 5 of the 2001 World Series.
The David Justice Trade
Date: June 29, 2000
The Trade: New York Yankees get OF David Justice; Cleveland Indians get RHP Jake Westbrook, OF Ricky Ledee, RHP Zach Day
This was the year in which Justice shrugged off an apparent decline to slam 41 home runs, including 20 in 78 games as a Yankee. He was also the ALCS MVP in 2000, largely by way of a go-ahead home run in the decisive sixth game.
The Juan Soto Trade
Date: December 7, 2023
The Trade: New York Yankees get LF Juan Soto, CF Trent Grisham; San Diego Padres get RHP Michael King, C Kyle Higashioka, RHP Jhony Brito, RHP Randy Vásquez, RHP Drew Thorpe
Soto was only a Yankee for one season, and his decision to accept a $765 million contract with the Mets has made him a heel for many Yankees fans. Even so, his 2024 season is arguably the best of a future Hall of Fame career, and he literally put the Yankees in their first World Series in 15 years with his homer in ALCS Game 5.
10. The Didi Gregorius Trade
2 of 11
Date: December 5, 2014
The Trade: New York Yankees get SS Didi Gregorius; Arizona Diamondbacks get LHP Robbie Ray, INF Domingo Leyba; Detroit Tigers get RHP Shane Greene
The Legacy
Since this was 12 years ago, here's a little reminder about who Gregorius was meant to replace at shortstop when he arrived in New York: Derek Jeter.
A tall order if there ever was one, and the jury was out on whether Gregorius would ever live up to his former billing as a top prospect. His first three seasons in the bigs had yielded an 88 OPS+ and just 2.8 rWAR in 191 games.
Five seasons later, Gregorius had averaged a 102 OPS+ and 3.0 rWAR as a Yankee before departing as a free agent.
That's more of a "good" shortstop than a great one, but the experience did prove that the Yankees were onto something when they tabbed Gregorius as Jeter's heir. We'd also be remiss if we didn't mention the 2017 playoffs, when he homered three times and had an .845 OPS in the Yankees' run to Game 7 of the ALCS.
Through Gregorius played his last major league game in 2022, he didn't officially retire from baseball until this past March.
9. The Curtis Granderson Trade
3 of 11
Date: December 8, 2009
The Trade: New York Yankees get CF Curtis Granderson; Arizona Diamondbacks get RHP Ian Kennedy, RHP Edwin Jackson; Detroit Tigers get RHP Max Scherzer, CF Austin Jackson, LHP Phil Coke, LHP Daniel Schlereth
The Legacy
The Yankees didn't get the best end of this trade. It was in Detroit that Scherzer blossomed as a future Hall of Famer, and Jackson was a 5-WAR center fielder for a couple years there.
The Yankees nonetheless had the right idea when they acquired the "Grandy Man." He had a classic Yankee Stadium swing from the left side of the plate, which always had the potential to unlock more power.
Which is exactly what happened. Granderson clubbed 108 home runs between 2010 and 2012, the fourth-most of any hitter in the league after José Bautista, Miguel Cabrera and Albert Pujols.
This was the beginning of a stretch of years in which the Yankees' playoff returns diminished following the 2009 World Series, but Granderson did his part to keep the flame lit. Specifically in 2010 and 2011, he had a 1.042 OPS in 14 total playoff games.
His last season with the Yankees was in 2013, when injuries limited him to 61 games and just seven home runs. Yet even though he ended up leaving for the Mets and throwing shade at Yankees fans, he should be (and seemingly is) fondly remembered in the Bronx.
8. The Gleyber Torres Trade
4 of 11
Date: July 25, 2016
The Trade: New York Yankees get SS Gleyber Torres, RHP Adam Warren, OF Billy McKinney, OF Rashad Crawford; Chicago Cubs get LHP Aroldis Chapman
The Legacy
It must have hurt the Yankees to watch Chapman go on to win the World Series with the Cubs, but it was ultimately no harm, no foul. The Yankees re-signed him as a free agent that winter.
Then in 2018, Torres arrived.
Rather, he landed like a meteor with the work he did at shortstop in 2018 and in 2019. He slammed 62 home runs across those two seasons, the most all-time for a middle infielder in the first two years of his big league career. Torres was also a driving force for the Yankees in the 2019 playoffs, hitting .324 with three home runs and 10 RBI in the run-up to Game 7 of the ALCS.
It's unfortunate that the rest of Torres' Yankees career never lived up to those first two seasons, specifically in the power department. He hit just 76 long balls in his last five years with the Yankees, just 14 more than in his first two alone.
Even so, Torres was ultimately one of the better infielders in the American League between 2018 and 2024, with 15.9 rWAR that ranked 17th among his peers.
7. The Nick Swisher Trade
5 of 11
Date: November 13, 2008
The Trade: New York Yankees get RF Nick Swisher, RHP Kanekoa Texeira; Chicago White Sox get INF Wilson Betemit, RHP Jeff Marquez, RHP Jhonny Núñez
The Legacy
The 2008-09 offseason was the one in which the Yankees dominated free agency, spending hundreds of millions of dollars on CC Sabathia, Mark Teixeira and A.J. Burnett.
The Swisher trade, by contrast, kind of snuck in through the back door. After a successful run with the Oakland A's, he was coming off a down year with the Chicago White Sox at the precise moment when he should have been in his prime.
"We did our due diligence and we're hoping '06 and '07 are more representative of Nick Swisher," Yankees GM Brian Cashman said at the time. "That was a risk we were willing to take on."
Cashman was right. Swisher hit 105 home runs in four seasons as a Yankee, with a sturdy 124 OPS+ to boot. Some Yankees fans might remember that he tended to go cold in the playoffs, but let's do him the solid of remembering his homer in Game 3 of the 2009 World Series, which was ultimately a winning cause.
Swisher should also be fondly remembered for bringing an element of fun to the Yankees that felt alien, yet welcome. Even now, it feels amazing that they ever let someone with that much personality wear pinstripes.
6. The Giancarlo Stanton Trade
6 of 11
Date: December 11, 2017
The Trade: New York Yankees get RF Giancarlo Stanton; Miami Marlins get SS Starlin Castro, INF José Devers, RHP Jorge Guzmán
The Legacy
Consider this proof that a trade can be both a disappointment and an unequivocal win.
True, the Yankees acquired Stanton (and the remainder of his $325 million contract) when he was fresh off winning the NL MVP after a 59-homer season. And true, they have never gotten anything like that from him. His best season as a Yankee saw him post 4.4 rWAR in 2018, with injuries otherwise limiting him to an average of 76 games per season since then.
Among Yankees, though, only Aaron Judge (329) has hit more home runs than Stanton (189) since 2018. Stanton has also owned October in this span, clubbing 18 playoff homers to Judge's 13.
Still another point in Stanton's favor is that he absolutely tortured the Boston Red Sox in his early days with the Yankees. Between 2018 and 2022, he posted a .931 OPS with 14 home runs and 43 RBI in 55 games against Boston.
On top of all this, the Stanton trade never amounted to more than salary relief for Miami. The Marlins have gotten a total of 2.4 rWAR from the deal, and nobody involved has played for them since 2024.
5. The David Cone Trade
7 of 11
Date: July 28, 1995
The Trade: New York Yankees get RHP David Cone; Toronto Blue Jays get RHP Marty Janzen, RHP Mike Gordon, RHP Jason Jarvis
The Legacy
Let's get one thing straight about the inclusion of the Cone trade in this discussion: it wasn't necessarily assured to start a long-term partnership.
Cone was a pending free agent when the Yankees got him in 1995, and he ended up re-signing as a free agent not once, not twice, but thrice. That's how a half-year rental trade turned into six years in pinstripes for Cone.
Yet even if this valuable context, it's missing the forest for the trees. What matters is that Cone was instrumental in the Yankees' return to glory in the 1990s, and not just because he was one of the best pitchers in the league (i.e., 18.6 rWAR, 142 ERA+) between 1996 and 1999.
He further enhanced his icon status by pitching a perfect game in 1999 and by working as a steady hand with the Yankees' World Series winners in 1996, 1998, 1999 and 2000. All told, they won eight of the 12 games he appeared in.
After his initial retirement in 2001, Cone first worked as a YES Network analyst in 2002 and has been with the broadcast crew consistently since 2011.
4. The Tino Martinez Trade
8 of 11
Date: December 7, 1995
The Trade: New York Yankees get 1B Tino Martinez, RHP Jeff Nelson, RHP Jim Mecir; Seattle Mariners get LHP Sterling Hitchcock, 3B Russ Davis
The Legacy
That 1995 season was the one in which Don Mattingly had finally had enough after 14 years without a World Series ring. Once he retired, the Yankees needed a new first baseman.
Enter Martinez, who was fresh off helping the Seattle Mariners deny Mattingly and the Yankees in the 1995 ALDS. That year had established the lefty swinger as a capable slugger, as he had cranked 31 home runs in only 141 games.
That was pretty much the same Martinez that the Yankees ended up enjoying through the 2001 season. He hit 175 home runs in six seasons, with a peak of 44 in a 1997 season that saw him finish second in the AL MVP voting.
Nothing wrong with that. Nothing wrong with four World Series titles either. Even if Martinez wasn't the most consistent October contributor, he did have that game-tying homer in Game 4 of the 2001 World Series.
Don't worry, Jeff Nelson. We haven't forgotten about you. As he also won four rings as a key setup man for Mariano Rivera, how could anyone ever do so?
3. The Roger Clemens Trade
9 of 11
Date: February 18, 1999
The Trade: New York Yankees get RHP Roger Clemens; Toronto Blue Jays get LHP David Wells, LHP Graeme Lloyd, INF Homer Bush
The Legacy
The Yankees had to give up a very good pitcher to do this deal. Wells finished third in the AL Cy Young Award voting in 1998, and would do so again in 2000.
Even at the time, though, the mood in New York was one of giddiness. The Yankees had tried to sign Clemens in 1996, when he was merely a three-time Cy Young Award winner. By the time they got him, he'd added two more to his collection.
If anyone wants to get technical, it was only courtesy of a contract extension that Clemens eventually won his sixth Cy Young Award in 2001. He also had to re-sign as a free agent to come back for the 2003 season.
All the same, he posted 19.7 rWAR across those five initial seasons in New York, all while averaging over 200 innings per season. The Yankees also won 11 of his 17 playoff starts, highlighted by a 15-strikeout one-hitter in 2000 that has the highest Game Score of any postseason start in history.
For Clemens, specifically, it might have been his first two seasons with the Yankees alone that made it all worth it. Before those, he had zero World Series rings. After those, he had two.
2. The Paul O'Neill Trade
10 of 11
Date: November 3, 1992
The Trade: New York Yankees get RF Paul O'Neill, 1B Joe De Berry; Cincinnati Reds get OF Roberto Kelly
The Legacy
When the Yankees acquired O'Neill in 1992, he was already an All-Star and a World Series champion. More than that, he was a sure thing in a way that Kelly was not.
"We were looking for left-handed bats because I didn't think we had enough," said then-Yankees GM Gene Michael, who also added that trading the younger Kelly was "gambling."
Here's how it all worked out:
- Roberto Kelly, 1993-2000: 6.9 rWAR
- Paul O'Neill, 1993-2001: 26.7 rWAR
O'Neill had his best years as a Yankee, notably making four All-Star teams and winning the AL batting title with a .359 average in the strike-shortened 1994 season. Of course, he also added four more World Series rings to his collection.
O'Neill had his No. 21 retired by the Yankees in 2022, and is currently in his 24th season as an analyst for the YES Network. It's not easy to become a Yankees institution, but the former Red has done so.
1. The Alex Rodriguez Trade
11 of 11
Date: February 16, 2004
The Trade: New York Yankees get SS Alex Rodriguez; Texas Rangers get 2B Alfonso Soriano, PTBNL (INF Joaquin Arias)
The Legacy
The legacy of this trade is… complicated, to say the least. Rodriguez spent 12 years with the Yankees, a he was some kind of lightning rod for seemingly all 4,380 days.
The Yankees ultimately saved $40 million on the $275 million contract that Rodriguez signed upon opting out and becoming a free agent in 2007, due to his his second PED-related controversy. The chilly relationship with Derek Jeter was weird, too, and we probably shouldn't get into the tabloid stuff.
And yet, A-Rod is seventh on the Yankees' all-time home run list and 10th among their all-time hitters in rWAR. Without him, they also don't win the World Series in 2009, in which case they'd currently be on a 25-year championship drought.
A-Rod's peak as a Yankees was certainly between 2004 and 2007, when he won two MVPs and averaged 43 home runs and 7.7 rWAR per season. By comparison, the Rangers got a total of 3.7 rWAR out of Soriano in two seasons.
Love him? Hate him? That's up to you. What's for sure is that if Brian Cashman ever gets a chance to do this trade over again, the smart thing would be to do exactly what he did in February of 2004.
Stats courtesy of Baseball Reference, FanGraphs and Baseball Savant.
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