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Brian Cashman’s Lost Years: A Look Back at a Decade of Moves PART 3:

By Patrick Gunn

November 12, 2023


Hello, it’s been a minute since I continued this series. Given that Brian Cashman had an, er, loud week, there’s no better time to look back on his moves. I’ve already delved into his major free-agent decisions and his offseason trades, so let’s look at his deadline moves. Cashman has swung between nothing deadlines and taking some of his biggest swings as a General Manager. Let’s take a look back at Cashman’s career at the deadline.

2014: Acquired Stephen Drew from the Red Sox for Kelly Johnson; acquired Martín Prado from the Diamondbacks for Pete O’Brien

Results: Mostly small moves in a mediocre season. Drew had his moments as a utility player in NYC, with some pop but nothing incredible but neither did Johnson. And Prado ended up being a stud for the second half in New York, particularly in September, and helped them land Eovaldi.

2015: Nada

The Yankees could have used some help in a wild card push but decided to fold, just trading Dustin Ackley for a few minor-league pitchers. They did enough to make the playoffs, but you wonder if a larger push would’ve helped New York win the division.

2016: Waving the White Flag: Yankees Trade Away Aroldis Chapman to the Cubs, Andrew Miller to the now-named Guardians, and Carlos Beltrán to the Rangers for Gleyber Torres, Adam Warren, Billy McKinney, Rashad Crawford, Clint Frazier, Sheffield, Ben Heller, J.P. Feyereisen, Dillon Tate, Swanson, and Nick Green

Results: The only time the Yankees have sold at a deadline in recent memory. The 2016 season was a wash, so the Yankees dealt three vets for prospects.

(Briefly: I also forgot to mention the Miller signing, which I regret because Miller might be one of Cashman’s best signings. He brought in an elite reliever at a fair deal and he pitched like an elite reliever.)

So, did the Yankees win all of these moves? Hard to say yes. Torres is the biggest win here, and despite struggles in 2020 (which can be forgiven because of the COVID year) and 2021, Torres has been a steady contributor as a second baseman. His defensive lapses can be frustrating, but Torres is still an above-average second baseman.

Aside from Torres, Warren’s second stint in New York went well. He bounced back from a poor 2016 in Chicago and pitched great in 2017 (2.35 ERA, 3.03 FIP) and it’s a shame they traded him in 2018 to avoid a roster crunch but also he hasn’t pitched too well after that. Tate ended up going to Baltimore in 2018 for Britton, and Swanson never got a chance in New York but also didn’t see himself apart in the Yankees’ system.

The real question marks come from Clint Frazier and the Cleveland portion of the deal. Sheffield ended up being a centerpiece in the Paxton trade, and Heller and Feyereisen never got a real shot in New York. Frazier became a polarizing figure, too odd for the Yankees’ more conservative franchise but also rarely given a full runway to perform. He had rough injury luck, his concussion in 2018 that came in Spring Training and affected his season, and then the 2021 season looming large. Frazier had moments, but his “legendary bat speed” never consistently showed up, along with mediocre at best defense. He was an odd fit in the Yankees’ system and injuries didn’t help.

What to make about this deadline? Prospects in baseball are unfortunately fickle, it’s hard to know when a player in baseball will succeed regardless of their pedigree. Torres is a good example: forcing him at shortstop put him in a poor position, but moving him back to second may have saved his career. Frazier, meanwhile, just was a poor system fit. These moves were billed as trades that could set the Yankees up for the future when in reality, only one player is still here and performing.

2017: Back in the New York Groove: the Yankees Acquire Sonny Gray from the A’s, Todd Frazier, David Robertson, and Tommy Kahnle from the White Sox for Dustin Fowler, James Kaprielian, Jorge Matteo, Tyler Clippard, Ian Clarkin, Blake Rutherford, and Tito Polo

Result: Home run - for 2017 at least. I’ll start with the unambiguous positive: the Yankees gave away a struggling Clippard and two solid prospects who never broke out in the majors for three great contributors for this season. Frazier’s homecoming was not a rousing success, but he gave the Yankees solid at-bats and a positive clubhouse voice (and an iconic meme). Robertson’s second stint in New York went about as well as his first, which is exceptional: a reliable high-leverage reliever with a lot of strikeouts and fist bumps. His 2018 (3.23 ERA) was less than his 2017 post-deadline (1.03), but a positive move nonetheless. And Kahnle had a down 2018 but a stellar 2017 and 2019 more than makeup for that, although it’s a shame he ended this stint injured.

Now Gray did pitch solidly in 2017. A 3.72 is decent, albeit the 4.87 FIP, and high walk and home run rates were poor. And he had a decent start against Houston in the ALCS (five innings, two runs, one earned, two walks, four strikeouts). Then, 2018 happened. Gray has opened up on the fact that the Yankees forced him to throw too many sliders. He actually had decent results with that pitch, but he lost the feel for his four-seam fastball (batters hit .342 with a whopping .531 slugging and .420 xWOBA off the pitch) and lost his command. I wonder how Gray would’ve pitched with Matt Blake instead of Larry Rothschild as pitching coach. Gray didn’t work in New York and was traded in a salary dump move to the Reds and he’s returned to his solid form since. At least the Yankees prospects didn’t play all that well in Oakland (Matteo has been a solid contributor in Baltimore and Kaprilian has had moments but struggled to stay healthy).

2018: Plugging some holes: Yankees Acquire Luke Voit Lance Lynn, J.A. Happ, and Zack Britton (formerly Zach Britton) in deals, send out Giovanny Gallegos, Chasen Shreve, Luis Rijo, Tyler Austin, Adam Warren, Caleb Frare, Brandon Drury, Billy McKinney, Dillon Tate, Cody Carroll, Josh Rodgers

Result: Many highs and lows amongst this group. Happ may have overachieved in 2018 but still threw to a 2.69 ERA in 11 starts after the deadline before struggling against Boston in the playoffs. Drury won a Silver Slugger last season as a utility player for the Reds and Padres, but he took a few years to fully find his form and he didn’t get the time to grow in New York. Remember Lance Lynn being a Yankee? He had his moments - including a 7.1 inning, Nine strikeout start against his future team, the White Sox - but did not shine the way he did afterward in Texas and Chicago (although he did have a 2.17 FIP thanks to a high strikeout rate, so maybe he was better than the 4.14 ERA suggests) and eventually got moved to the bullpen. Britton - injured much of the first half of the season - approached his All-Star Form with New York and, despite a high walk rate (10.4%), he got outs (2.88 ERA). They did give up Dillon Tate in this deal, who has been decent in Baltimore (3.97 ERA, 4.03 FIP, 108 ERA+) in four seasons, but that deal feels like a win.

The player with the loudest impact on New York was Voit, the savage in the box. He mashed 14 home runs in 39 games down the stretch and helped jolt their lineup in a season in which Aaron Judge missed time early in the year. Of course, Voit provided more of a punch in 2019 and especially in 2020, but then he got injured in 2021 and the Yankees decided to go with another first baseman they acquired in a deadline deal. Shreve threw decently in the second half of 2018 but only made three appearances for the Cardinals in 2019 after being designated for assignment and optioned to Triple-A before a brief call-up and release. Gallegos, though, has shined in St. Louis, throwing to a 3.13 ERA with a 3.20 FIP since the deal. In terms of value, Voit has a higher bWAR from his New York stint than Gallegos (7.1 for Voit vs. 4.5 for Gallegos and counting), so this deal feels like a rare win-win.

2019: Yankees Acquire Edwin Encarnación from the Mariners in June for Juan Then; acquire 20-year-old Alfredo Garcia from the Rockies for Joe Harvey

Result: An infamously quiet deadline. Cashman could not get a deal done around the deadline but the one big name he brought in did help. Encarnación’s stint in the Bronx was brief - he joined the long list of players who missed time this season when he broke his wrist - but still hit 13 home runs in 44 games, good for a .531 slugging percentage, a .856 OPS, and a 123 OPS+. Still, the Yankees needed some reinforcements after a season of injuries plus a thin rotation. I wonder if the Yankees make it back to the Fall Classic if they added Marcus Stroman or Zack Greinke or even Robbie Ray and 2019 Zack Wheeler (that’s if the Mets were willing to make a trade with the Yankees).

2020: COVID season, Yankees Acquire Addison Russ for David Hale

Result: Not much to say here. The Yankees had another bout with injuries this season and that put them behind the eight-ball in a 60-game season. Russ never made it to the majors with the Yankees and retired in 2022, but he did have a high strikeout rate in the minors (11.6 K/9), so you can see where Cashman was thinking. The Phillies added Hale during their disastrous bullpen season, and he pitched in six decent games for the Fightins. New York certainly could have been more active this deadline rather than waiting for their stars to come back healthy.

2021: Going for it: Yankees Acquire Joey Gallo, Andrew Heaney, Clay Holmes, Anthony Rizzo, Joely Rodríguez for CF Kevin Alcántara, SS Diego Castillo, RHP Luis Cessa, SS Ezequiel Duran, 2B Trevor Hauver, RHP Janson Junk, RHP Glenn Otto, SS Hoy Park, RHP Elvis Peguero, 2B Josh Smith, RHP Alexander Vizcaino, LHP Justin Wilson

Result: The Yankees struggled in the first half of 2021 despite having a healthy Judge, Stanton, and Cole. So, the Yankees took some swings to improve the lefty-righty lineup balance in their lineup and bolster their pitching depth. And these players did help the Yankees reach the playoffs in 2021, albeit for just one game. Cashman may have reached too far in acquiring Heaney; they were not that desperate for starting pitching and the flyer on the struggling southpaw did not pay off (he did win a ring with the Rangers this year, though). Rodríguez had one of the most successful runs of his career in New York as a lefty specialist with a 2.84 ERA in 21 games. And what can you say about Holmes, a reliever struggling with his command in Pittsburgh turning into a legitimate back-of-the-bullpen arm who’s still (mostly) dealing in New York. He is a testament to the best of what the Yankees can do for players.

Rizzo had a great first weekend in 2021 before getting injured and hitting okay down the stretch. He then had a great first half in 2022 leading to a 30+ home run season before dealing with injuries. Then he hit excellently again in the first two months of 2023 before, well, that unfortunate collision. Cashman had the right idea bringing in Rizzo and there is still time for him to contribute. You could argue he has been an overall upgrade over Voit, but at the same time, the injuries have loomed large.

And Gallo, one of the most unfortunate moves Cashman has ever made. I still don’t have any regrets for Cashman bringing in Gallo, his lefty-pull power and solid defense made him a good fit in theory in the Bronx. In practice, Gallo never got in a rhythm in New York. Per usual, he struck out a lot (38.7% of the time to be exact) but he did not add enough power (25 home runs in 140 games, just a .368 slugging) to reach his all-star potential. As far as losses go, Duran has been decent for Texas and could be a solid depth piece for them going forward, but the Yankees did not lose too much here beyond names. Gallo’s struggles really define this deadline and the last three seasons; if he breaks out in New York, the Bombers probably have fewer holes at the plate. As is, this was a positive in the short-term and a mixed-bag overall.

2022: Too Many Injuries. Yankees Acquire Andrew Benintendi, Scott Effross, Frankie Montas, Lou Trivino, Clayton Beeter, and Harrison Bader for T.J. Sikkema, Beck Way, Chandler Champlain, Hayden Wesneski, Ken Waldichuk, Luis Medina, J.P. Sears, Cooper Bowman, Joey Gallo, and Jordan Montgomery

Results: Somehow, every major league player the Yankees acquired at this deadline has missed some time with injuries. All things considered, Beeter was a solid get for the Yankees to deepen their farm system especially given how Gallo performed in the Bronx. Hopefully, Beeter will make his way to New York soon. But my goodness, the injuries. Effross continued to deal in the 13 games he pitched for New York - and then he needed Tommy John surgery. Effross is still under contract in New York, so there is still time for him to shine in New York.

Benintendi had slowed down from his hot start (his OPS dropped from .785 on his last game with the Royals to .753 on August 20th). But he started to hit again - before injuring his wrist. He left in free agency, and the Yankees probably made the right call letting the light-power-hitting outfielder leave for Chicago. Montas probably has driven the most talking points, with the Yankees acquiring Montas after he dealt with some shoulder issues. He was healthy at the deadline, so the Yankees pivoted once Luis Castillo got sent to Seattle, and Montas struggled mightily (6.35 ERA in 8 starts) before missing the remainder of the season with a shoulder injury (sans a playoff appearance). He then missed most of this season with a shoulder injury, only appearing in the last series of the season. Trivino, also acquired in the Montas trade, bounced back with New York following a tough start in Oakland but missed the entire 2023 season because of injuries. You wonder if Cashman should have just splurged and gotten Castillo rather than moving to Montas, but Montas was pitching well in Oakland beforehand. Maybe he can come back on a prove-it deal.

At the time, the Montgomery trade confused me. Why ship off a reliable, good starting pitcher for an outfielder who is already injured? Well, Bader proved me wrong in the playoffs, showcasing his great defense and his timely hitting (5 postseason home runs in 2022). Meanwhile, Montgomery - after dominating in August 2022 - made one relief appearance for the Cardinals in 2022. So, all Bader had to do to prove Cashman right in 2023 was A) stay healthy and B) hit around league average. Bader did neither of those things. He started the season injured, but did provide another spark in May (.806 slugging percentage, 6 home runs in May). Then, he got hurt again, and never refound his stroke. Bader ended up with a meager 75 OPS+ for the Yankees before getting put on waivers in late August. Meanwhile, Montgomery became a postseason hero after another trade to the World Champion Rangers. Even as someone high on Montgomery, I never imagined him pitching like that. Arguably, the biggest failure of this trade was undervaluing Montgomery as someone who would not start in the postseason. Still, a lot of the criticism for this trade comes in hindsight; if Bader had hit for the Yankees, I think this one gets viewed differently. As is, the deal soured hard on Cashman.

The Yankees gave up some talented arms and former top prospects this deadline - namely, Sears, Medina, and Wesneski. Most of them have shown flashes but none have fully achieved their potential yet, which is fair for players in their first or second seasons in the bigs, with some (namely, the Oakland players) in a poor context for success. Still, it’s probably worth it to take such a hit in prospect depth if the Yankees won a title. And unfortunately, nearly all of the players the Yankees acquired got hurt.

2023: Two relievers, Yankees Acquire Kenyan Middleton from the White Sox and Spencer Howard from the Rangers

Result: Only the Yankees’ worst season in at least half a decade. The Yankees were still in striking distance at the deadline, even after struggles in July. And Cashman, inexplicably, decided to do next to nothing. Sure, Middleton helped their bullpen, but they needed more. The Yankees needed some lineup and pitching depth and got none of that. You can argue about a week deadline, but the Rangers (Montgomery, Max Scherzer), Astros (Justin Verlander), Diamondbacks (Paul Sewald, Tommy Pham), and Phillies (Michael Lorenzen) all made some big moves to help at the deadline. There were players the Yankees could have targeted, or done something like Atlanta’s 2021 deadline maneuvers. Or, the Yankees could have tried to sell some free agents and restocked their farm system. Cashman chose the indecisive route, leaving the Yankees worse off both for the stretch run and the offseason.

In Conclusion: It is hard to win a title at the trade deadline, but a few good moves can spark a title run. The closest Cashman has gotten to that was in 2017, with every player acquired (even Sonny Gray) contributing down the stretch. Other than that, the Yankees have switched between some depth moves and some big slurges. Admittedly, a lot of this analysis comes from hindsight, because you can see the thought process behind most of Cashmans’ biggest blunders, even Gallo, Montas, and Gray. Still, results are results, and Cashman has not made the one move needed to push the Yankees to the finish line in years. It is fair to wonder if Cashman should just have gone for the best players available every year rather than second options (Montas) or gone with high-risk-high-reward players at the margins (Heaney, Bader). In general, I feel Cashman has made some solid course-correction moves most seasons; at the very least, his risks in the summer are more justifiable than some of his offseason blunders. Regardless, Cashman has failed to find all the right moves in all the right places in recent trade deadlines.

What do you make of Cashman’s last decade at the trade deadline?



Robert Malchman
Robert Malchman
Nov 12, 2023

Cashman used to have a great touch, and this article highlights that. The last two seasons have been disastrous, though, which to me means it's time for fresh blood, fresh thinking, and for Cashman to be removed.

Nov 13, 2023
Replying to

ask me again in February


Alan B.
Alan B.
Nov 12, 2023

Brandon Drury lied to the Diamondbacks about the severity of his migraines, and that really showed up when he got here. As a fellow migraine sufferer, don't try to make excuses for him, because you can't.

What really happened in that meeting at the end of 2018, that DRob that he has never made it back here? Realistically, he would be my #1 target to sign.

I crunched the number years ago, Sonny Gray was a decent pitcher for the Yankees wearing the road grays, but wearing the pinstripes, in Yankee Stadium, he was a complete disaster.

Adam Warren. Ah, one pitcher who pitched better in a Yankees uni than he did anywhere else.

The Yankees over the Cashman years,…

Robert Malchman
Robert Malchman
Nov 13, 2023
Replying to

I know this is stupid, but I always want to refer to him as "Ian Drury." Maybe I'm just a Blockhead.

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