Brian Cashman’s Lost Years: A Look Back at a Decade of Moves PART 2

By Patrick Gunn

Brian Cashman’s last 10 years of moves have not propelled the Yankees to a title. But he has had his successes on the trade market - and his failures. His trades have brought more success than his free-agent signings (which you can read more about here), and Cashman has made moves that surprised and others that worked in theory but not in practice. These are the trades Cashman has made in the offseason to decent results.

Again, this piece is getting long, so I'll have more on his trade deadline highs and lows soon.

2015: Yankees acquire Nathan Eovaldi, Garrett Jones, and Domingo Germán from the Marlins for Martín Prado and David Phelps

Result: This deal was one of good intentions but mediocre results. Prado had a fantastic stint with the Yankees after his 2014 trade and finished his career with four decent years in Miami, and Phelps was a decent reliever-starting swingman who got even better after leaving New York. Jones did not hit in his only year in New York, but this deal was about one player: Eovaldi. The Yankees saw his 100 mph heater and solid splitter and decided to take a chance that they could improve his command if he stayed healthy. And, in the second half of 2015, the Yankees had an improving pitcher:

56.1 IP in 9 starts, 3.67 ERA, 20.7 K%, 9.5 BB%, just 2 home runs allowed

Nothing incredible, but still a solid stretch. Then, in 2016 he regressed and then he needed Tommy John. He left in free agency to sign a two-year deal with the Rays, and the rest is history. Eovaldi did become a solid starting pitcher and an excellent postseason performer, just not in New York. If he stays in the Bronx and pitches like he did in Boston and now with Texas, this trade looks completely different. He just didn’t stay healthy here.

Germán has played the most games for New York out of any players in this deal and he’s been a mixed bag. His highs are perfection on the mound (literally) and his lows are…what led him to miss an entire season because of a domestic violence situation. He’s a fine middle-innings reliever and replacement starter, but the domestic violence case and the end to his tenure outweigh his positives.

2015: Acquired Didi Gregorius in three-team trade for Shane Greene.

Result: Decent win for Cashman here. Gregorius struggled at first as Derek Jeter’s replacement but he ended up with three-consecutive 20 home run seasons and played solid defense in New York while being an upstanding citizen. His metrics and numbers feel lower than I remembered from his time in NY (102 OPS+, .446 SLG) and he always struggled to get on base. Regardless, he’s one of the last solid left-handed power hitters the Yankees have acquired during this stretch, which may say more about the Yankees being unable to add quality left-handed power hitters. Greene has had an up-and-down career, with an All-Star season in 2019 along with some poor years around that. He even briefly returned to the Yankees last year - for one game - but this trade is a positive, even if the numbers for Didi are not anything overwhelming.

2015: Reliever deals - Acquired Justin Wilson, Chasen Shreve, and David Carpenter for Francisco Cervelli and Manny Banuelos

Ah, Cervelli and Banuelos. It appeared Cervelli would become the Yankees’ next starter at one point, but then came injuries and a steroid suspension. He ended up becoming a solid and beloved backstop in Pittsburgh. And Banuelos, one of the killer B’s, just never stayed healthy enough to make it to the show but did come back last season for a decent and brief stint.

As for the relievers the Yankees’ got in return, a mixed bag. Wilson ended up pitching great during this season, one of the Yankees' top back-end options in 2015. Shreve got off to a great start before allowing too many home runs. He’s had a decent career as a journeyman since. Carpenter, unfortunately, got hurt early and has barely played in the bigs since 2015.

2016: Yankees acquire Luis Cessa and Chad Green from the Tigers for Justin Wilson

A classic Cashman value move. He was turning one great season from Wilson into two solid relievers. Cessa struggled to stay healthy and consistent, but his last two-and-a-half years he served as a decent contributor. But the real winner from this deal is Green, who at his best was one of the best relievers in baseball running off his high fastball and ringing up strikeouts (11.6 K/9 as a Yankee). He gave up too many home runs at times, but getting him for Wilson is an absolute win.

2016: Yankees Aroldis Chapman for Rookie Davis, Eric Jagielo, Caleb Cotham, and Tony Renda.

Result: This trade still feels gross nearly eight years later. Make no mistake, the Red made this move as a dump-off: they had to nix a trade with the Dodgers because of his domestic violence allegations, so they sold him off. Yes, none of the four players the Yankees traded made an impact in Cincinnati (Davis briefly pitched in the majors, and Jagielo was a higher prospect who struggled to hit after the trade). And yes, Chapman pitched well enough after his suspension to get the Yankees Gleyber Torres at the deadline. Still, the Yankees should be ashamed they took on Chapman after nearly no one else would take him on.

2016: Yankees acquire Aaron Hicks from the Twins for John Ryan Murphy

Result: Good trade, but it stinks Hicks’ Yankees tenure ended the way it did. Hicks never found his top-prospect form in Minnesota, so the Yankees took a chance on him. Given that Ryan Murphy barely played for the Twins, the deal is a win, but people forget Hicks’ solid 2017-2020:

.247 BA, .362 OBP, .457 SLG, 120 OPS+. 2.5 average bWAR

Nothing remarkable, but he reliably got on base, played solid defense, and hit some big home runs; his performance in their 2019 regular season comeback against the Twins still sits in my head. He earned that extension from the Yankees, but injuries led to poor play and a release. Thankfully, Hicks bounced back with the Orioles this year. Maybe that change of scenery will help Hicks regain form. Hicks left a positive impact as a role player in New York even with a poor final chapter.

2016: Yankees acquire Starlin Castro from the Cubs for Adam Warren and Brendan Ryan

Result: The Cubs wanted to move on from longtime stalwart Castro to make way for their younger, all-star infield. They took on pitching depth and gave the Yankees a new second baseman in Castro. His overall numbers don’t give him much credit (just a 3.2 bWAR, 99 OPS) but he was an all-star in 2017. He didn’t make as many of the mental lapses in the field at second base as he made at shortstop in Chicago. After this point, Castro had dark moments, but he was a fine stopgap second baseman in New York.

2017: Yankees Acquire Albert Abreu and Jorge Guzmán for Brian McCann

Result: This is mostly a salary dump move to make way for Gary Sánchez. Whatever you think of him, Abreu has at least had his moments in New York and has been a fine innings-eater despite his lows. Still, you wonder if the Yankees could have gotten more for McCann even after a mediocre stint in the Bronx.

2018: Yankees Acquire Giancarlo Stanton from the Marlins for Starlin Castro, Jorge Guzmán, and Jose Devers

Result: The Stantonian trade, one that defined this offseason and the years that have come after. This is the move many Yankees fans see as a reason for their struggles, that they never should have added this massive contract for a player with this injury history, and his performance has justified their anger. And my first thought more than five years later: I still make this trade 10/10 times. The Bombers gave up shockingly little for Stanton, Castro had a lower War in two healthy seasons in Miami than Stantons’ 2018 season. Guzmán and Devers barely played for the Marlins. Stanton has had at least one all-start season, some solid postseason moments (11 home runs and a .635 slugging), and a positive clubhouse impact.

And look, this deal was obviously a salary dump for them; they wanted to rebuild following Derek Jeter and the company’s purchase of the team and had to off Stanton. Still, the Yankees should be willing to take some risks like this. He entered his age-29 season in 2018, still in his prime. The Yankees as a franchise should be able to take on big contracts like this and also pay the Bryce Harpers, the Shohei Ohtanis, and the Juan Sotos of the world. If anything, the failure of the Yankees is not just that they’ve brought Stanton itself, it’s that they haven’t gone after any other big-named bats in free agency. And Stanton still has the time to make up this value. Right now, the outcome of the trade has been far from ideal, but Cashman did not tank his career trading for Stanton.

2019: Acquired James Paxton from the Mariners for Justus Sheffield, Erik Swanson, and Dom Thompson-Williams

Results: Another high-risk but solid idea from Cashman that got blown up by injuries. Paxton had an inconsistent first season in New York but was able to make a still career-high 29 starts and pitch to a 3.82 ERA while striking out a lot of batters (29.4% of batters to be exact). Then he didn’t look right in 2020 and only made five poor starts before ending his season with a back injury and has barely played since this deal. Again, Cashman and the Yankees had the right idea bringing in a pitcher who can strike out lineups for days and be dominant when healthy, he just did not stay healthy.

On the return side, Sheffield was the centerpiece and he’s now in Atlanta’s system. He had a decent 2020, but hasn’t found his command. He’s only 27 years old, so there’s still a chance he find that top prospect form. The best player to come out of this trade may be Swanson, who’s had a 2.60 ERA over the last three seasons with the Mariners and Blue Jays while striking out 29.4% of batters faced while walking just 6.7% of those hitters. He did struggle in his first two years in Seattle but has had a solid last three seasons. You give the Yankees’ bullpen enough credit to survive over the last three years, but this trade goes as mixed bag.

2019: Acquired Mike Tauchman from the Rockies for Phillip Diehl

Result: A key face of the 2019 next-man-up, savages in the box Yankees. He had a 128 OPS+ that season in 87 games in a year when they needed the outfield help. Afterward, Tauchman didn’t reach that high, but they were able to turn that into Wandy Peralta and they gave up Diehl, who didn’t pitch well in Colorado. He left the majors for the Korean league in 2022 where he posted a solid year and that carried over into a good 2023 for the Cubs in the U.S. Maybe there’s more in the tank for Tauchman.

2021: Acquired Jameson Taillon from the Pirates for Miguel Yajure, Roansy Contreras, Maikol Escotto, and Canaan Smith

Result: Cashman really likes taking swings on former top prospects with histories of injuries, huh? Taillon did stay healthy in New York, thankfully, and had two around-average seasons. No, he never consistently pitched like the ace the Pirates hoped they had, but he was able to give the Bombers consistent innings for the last two seasons. And he did help the Yankees make the playoffs in a close 2021 race with a great start against the Rays on the last day of the season. And it feels too soon to judge the prospects in this deal, but Yajure is in the Giants’ system and the other players have barely played.

2021: Sent Adam Ottavino and Frank German to the Red Sox

Result: Apologies for forgetting to discuss Ottavino in my last piece. He had a solid 2019 where he may have overachieved given his walk rate (14.1%) and the Yankees didn’t trust him in the playoffs, but still hard to argue with a 1.90 ERA and a 3.44 FIP. His 2020 went worse, but much of his 5.89 ERA came from one awful outing where he allowed six runs and two walks to the Blue Jays in their minor league stadium without retiring a batter. That’s half the runs he allowed all season in a shortened year. His 3.52 FIP was nearly identical to 2020 with better walk and strikeout percentages. Regardless, the Yankees wanted to drop his contract and sent him in a salary dump to rival Boston. He had a poor year with the BoSox but has been solid in Queens. I think the Yankees gave up on Ottavino too early even with his control issues.

2022: Goodbye Sánchez and 2019 Next-Men Up Crew: Yankees Acquire Josh Donaldson, Isaiah Kiner-Falefa, Ben Rortvedt, Jose Trevino, and Justin Lange for Sánchez, Gio Urshela, Luke Voit, Albert Abreu, and Robby Ahlstrom

Result: Oof. The Yankees and Sánchez needed a split after several ugly years with the Yankees failing to put their once blue-chip player in a position to thrive. Also, the Yankees wanted to improve their defense across the field, not just at catcher. That meant keeping Anthony Rizzo and sending off former savage in the box Luke Voit. Also, they took a chance on Donaldson’s high exit velocities, IKF’s ability to play shortstop, and Trevino’s defense in a myriad of deals, including a goodbye to the well-liked Urshela.

This worked poorly for New York. The Twins may not have gotten much from Urshela and Sánchez at the plate, but they were positive locker room fixtures, and getting rid Donaldson’s salary helped them sign Carlos Correa. As for the Yankees, Donaldson regressed hard in his late 30s, and he became more of a nuisance from the racist comments towards Tim Anderson and untimely mental lapses. IKF is a good person who did not deserve the vitriol Yankees fans have directed towards him, but he did not hit nor field well to play that much at shortstop last season. He served as a solid utility player in 2023 considering the circumstances, but not good enough for the Yankees to resign him next season considering his lack of power. Rortvedt missed nearly all of 2022 with injuries and has hit at the minors but seems more like a backup catcher. Trevino did surprisingly make the 2022 All-Star team thanks to a solid offensive first half, and the pitchers and players generally like him. Regardless, his bat has returned to Earth with a well-below-average OPS and he should not have played through injuries this season. They only gave up Abreu to get Trevino, so it’s a good move, but the Bombers overexposed him. These deals philosophically were questionable from the start and represented poor allocations of resources that led to this year’s collapse.

That's Cashman's offseason moves. I think Cashman made some good swings with Eovaldi, Stanton, and Paxton, and has some good value moves. Regardless, the lack of impact left-handed bats is glaring and he could have focused on healthier starters over the oft-injured but intriguing talents. And his 2022 swing backfired hard. What do you think of these moves? And what players did I miss that deserve more of a conversation?