5 best and worst Yankees moves made by Brian Cashman, from acing Gerrit Cole signing to Sonny Gray debacle originally appeared on The Sporting News . Add The Sporting News as a Preferred Source by clicking here .
Over the past decade, the New York Yankees have had the luxury of one of the best players in baseball in Aaron Judge, but have still not been able to break their World Series drought.
General manager Brian Cashman has been on the job for almost three decades, producing an incredible amount of consistent success while also falling short of a championship too often. In recent years, Cashman has been tasked with building a team around Judge, which has not produced the level of dominance that many fans expect.
Cashman is not afraid to make bold moves, which leads to both high-profile hits and misses. In some cases, he has nailed acquisitions to build a championship-caliber team, and in others, he's missed badly in wasted opportunities.
Here's a look at the best and worst moves by Cashman since Aaron Judge's rookie season in 2017.
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Gerrit Cole was the best free agent available following the 2019 season, and it was clear his preference was to sign with the Yankees. Still, Cashman landing the ace on a nine-year, $324 million deal instantly filled New York's biggest hole and gave Judge a co-star in the rotation.
In six years with the Yankees, Cole has pitched to a 3.19 ERA while winning his first Cy Young award in 2023 and breaking the team's strikeout record in 2022. He was the ace of a team that made a World Series run in 2024 and has also provided a veteran presence for the rest of the pitching staff.
The Yankees are not known much for their drafting and developing, but the emergence of Cam Schlittler and Ben Rice might have extended the team's window. The Yankees drafted Schlittler in the seventh round of the 2022 draft, and Rice in the 12th round of the 2021 draft, and they ended up being the team's two best players in 2026.
Schlittler is the heavy favorite to win the AL Cy Young award, giving the Yankees another ace to go along with their impressive veteran rotation. Rice, meanwhile, led the team with 41 home runs and became one of the few homegrown Yankees players to reach that milestone.
There is an argument that trading for Juan Soto was one of Cashman's best moves, but Soto signing with the New York Mets after his lone Yankees season dampened that deal a bit. Instead, Cashman's pivot after losing Soto was less obvious but perhaps more impressive, even if it hasn't yet led to a return to the World Series.
The biggest name the team added after the 2024 season was Max Fried, who signed an eight-year, $218 million deal to head to New York. Fried was stellar in 2025, pitching to a 2.86 ERA while leading the league in wins as Cole missed the entire season. and despite dealing with injuries in 2026, he still had a 2.80 ERA in 20 games.
Most notable, Fried was dominant in two playoff starts against the Boston Red Sox , which is always key for the Yankees.
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Bellinger was also part of the pivot after losing Soto, directly replacing the superstar in the outfield next to Judge. However, there is a legitimate argument that Bellinger is a better fit than Soto next to Judge even if Soto is the better player overall, as his first two years with the Yankees has shown.
Bellinger took over in left field and immediately steadied the position, which the team hadn't properly filled since Brett Gardner left. The veteran should win a gold glove for his excellent defense in 2026, and his swing is perfect for the short porch in Yankee stadium.
To acquire Bellinger, Cashman traded the Chicago Cubs just Cody Poteet before the 2025 season, then he signed Bellinger to a five-year deal in 2026. Overall, Bellinger proved to be a perfect fit for the Yankees.
In the post-Mariano Rivera world, the Yankees closer spot has changed quite often. Pitchers like Aroldis Chapman and Clay Holmes filled in admirably but had enough lowlights to make Yankees fans lament missing the all-time saves leader.
Therefore, acquiring David Bednar at the 2025 trade deadline proved to be wise. Bednar kept up his closer dominance from his time with the Pittsburgh Pirates , supplanting Devin Williams as the Yankees closer ahead of the 2025 playoffs and keeping it for all of 2026. In 1.5 seasons with New York, Bednar had a 2.45 ERA and 45 saves as one of the more reliable relievers in the league to anchor what has been a more inconsistent bullpen overall.
MORE: Full Yankees playoff history with Aaron Judge
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Cashman's first attempt at bolstering the Judge-led Yankees didn't go as expected. At the 2017 trade deadline, New York acquired Sonny Gray, a then-young starting pitcher with team control to match New York's roster, instead of landing Justin Verlander, who was months away from a career renaissance with the Houston Astros .
Gray was fine in his first few months with the team, pitching to a 3.72 ERA after the trade deadline in 2017, but he had one of his worst seasons in 2018. Gray produced a 4.90 ERA in 2018, struggling mightily at home, while he and the organization never got on the same page regarding his pitch style. To make matters worse, Verlander went on to torment the Yankees in the playoffs three times as an Astros ace.
The Yankees had to trade Gray following the 2018 season, getting virtually nothing back in return.
With Gray struggling in 2018, the Yankees traded for Happ to bolster its rotation, and Happ pitched well down the stretch before producing a poor playoff start. When Happ reached free agency, though, Cashman brought back the lefty on a deal that aged poorly right away.
The Yankees signed Happ to a two-year, $34 million deal after the 2018 season, but Happ then pitched to a 4.91 ERA in 2019. New York won 103 games that season, but when the playoffs came around, they were a starter short when they faced the Astros, and he even gave up a walk-off home run in Game 2 of the ALCS to Carlos Correa.
Happ rebounded well in the shortened 2020 season, but the team didn't trust him much after his rough 2019.
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The Yankees had a tough start to the 2021 season, leading to Cashman having a very busy trade deadline. The biggest deal was a trade for Joey Gallo, who was having an All-Star season with the Texas Rangers , as the Yankees wanted to add some lefty power.
Instead, Gallo's production plummeted. After totaling an .833 OPS in Texas over seven seasons, Gallo had a .660 OPS with the Yankees that spanned a calendar year, leading to the Yankees dumping him at the 2022 trade deadline. The lefty slugger both lost some of his power and had more issues defensively, turning strengths into weaknesses.
At the start of the 2022 season, the Yankees wanted to add some competitiveness, so they acquired former AL MVP Josh Donaldson from the Minnesota Twins in a deal that included fan favorite Gio Urshela and Gary Sanchez. However, Donaldson ended up being closer to retirement than his prime, proving to be a bigger distraction than asset.
Donaldson went from an .827 OPS in 2021 to a .682 OPS in 2022, and provided the team more lowlights than highlights both on and off the field. By the end of the 2023 season, the Yankees waived Donaldson, who went on to finish his career for the Milwaukee Brewers before retiring in the offseason.
The Yankees had a historically strong start to the 2022 season, but needed reinforcements when the trade deadline came around. While Cashman was busy acquiring players, most of them fizzled through injuries with Frankie Montas being the biggest bust of an acquisition.
Montas had a great 1.5 years with the A's in 2021 and the first half of 2022, leading to the Yankees believing he was the missing piece. Instead, Montas' lengthy injury history continued in New York, as he pitched to a 6.35 ERA to end the 2022 season while trying to pitch through an arm injury. He then missed almost the entirety of the 2023 season, returning to record four outs in the final game of the year, before leaving in free agency.
