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Brian Cashman’s Lost Years: A Look Back at a Decade of Moves PART 1

By Patrick Gunn

October 7, 2023


Brian Cashman faces an uncertain future in the Bronx. His Yankees team has finished one of its worst seasons under his tenure with writers across the internet - including some on this blog - actively wanting New York to bring in someone new in the front office. Now, he surely is not the only one at fault for the team’s 2023 failures, but Cashman has put himself in a frustrating position. The Yankees have just finished an underwhelming decade of baseball, with the Core Four’s retirement leading to a period of mediocrity leading to some high win totals but little postseason success and then last season.

In short, the Yankees have been consistently decent but rarely have found the combination of excellence needed to win a title again. And it’s fascinating that Cashman’s job has been questioned more now than it was after 2016 when the Yankees missed the playoffs for the third time in four seasons. In terms of Cashman, one question stands out to me: how have the last decade of moves shaped his teams? His moves show a willingness to make a few big swings on veterans, but rarely the types of drastic moves the Yankees should look into - particularly on the position player front. Let’s look back at the major moves Cashman has made since the 2013-14 offseason and how they lead to today.

Caveat: while writing this, I realized looking back at 10 years of front-office is quite the undertaking. So, we’ll cap off today’s piece with just the big free-agent signings and re-signings. By that, I mean players going into free agency, so no extensions here (apologies to Aaron Hicks and Luis Severino). Also, I mainly want to look at the larger signings, so most contracts two years or less won’t come in this piece.

The Big Signings:

2014: In their push to win one last title with Derek Jeter, New York Signed Masahiro Tanaka (7 years, $155 million), Jacoby Ellsbury (7 years, $153 million), Brian McCann (5 years, $85 million), and Carlos Beltrán (3 years, $45 million)

Results: Not what you’d want. Only one of these players - Tanaka - finished their contract with the Yankees. He’s easily the biggest win of this group. No, Tanaka never consistently pitched like the ace he was in Japan, but he still was a reliable, effective starter in both the regular and post-seasons. And a majority of the innings he threw came after injuring his elbow and electing not to have surgery.

After Tanaka, the effectiveness gets murky. McCann hit home runs but rarely hit consistently like he did in Atlanta. He was a decent guy, but probably not worth that investment and they moved on from him quickly after Gary Sánchez’s breakout. Beltrán had a horrendous 2014, then returned to his career norms in 2015 and the first half of 2016 before getting traded to Texas. He ended with a 116 OPS+ with New York. Overall, this signing worked despite the ugly first season.

Then, there’s Ellsbury. After a decent first season (3.8 bWAR, .747 OPS, 111 OPS+), Ellsbury struggled to stay healthy and consistently hit. He averaged 124 games and an 89 OPS+ over his last three seasons in New York. He still averaged 2.1 bWAR over the stretch mainly because of his defense, which is fine for a utility player but not for a centerfielder paid more than $20 million a year. Oh, and he didn’t play any of the final three years of his contract. Coupled with the fact that he chose to bring in the oft-injured Ellsbury over keeping Robinson Canó, Cashman easily made one of his worst moves with this signing. And this signing looms large over the group, as the Yankees didn’t start contending again until after three of these four players left the picture.

2017: Yankees Resign Aroldis Chapman (5 years, $86 million, later 3 years $48 million)

Results: I’ll have more on Chapman in the trades section, but this will be about after his tenure signing his contract. On the surface. Chapman performed in the regular season for the most part. Even with an atrocious final season, Chapman pitched to a 3.05 ERA with a 3.01 FIP, and 142 ERA+ while striking out 37.0% of all batters he faced.

Now, in the playoffs, he only gave up five runs in 21 innings - good for an ERA under 2.20. Unfortunately, those runs he allowed were timely: walk off to the Astros in 2017, walk off to Altuve in 2019 where he made the infamous smile, and game-winning home run to Mike Brosseau against the Rays in 2020. He’s more remembered for his blow-ups rather than his successes because they cost the Yankees multiple close games in close series. Not to mention that Chapman’s rough stretches in New York were ugly, walked a lot of batters (13.1% of batters faced), and ended his contract walking away from the team before the playoffs. Also, it should be discussed more how the Yankees kept Chapman around after his horrific domestic violence incident in 2015 which he showed little remorse for. This is a move that feels like a net negative despite the solid pitching because of everything surrounding Chapman the person along with the abysmal lows.

2019: Yankees resign Trade Deadline Invitees Zack Britton (3 years, $39 million with option for fourth-year option taken) and J.A. Happ (two years, $34 Million, third-year option declined)

The Yankees pushed to keep two of their big deadline acquisitions at moderate deals for mixed results. Britton had two solid seasons (1.90 ERA across 2019 and 2020 with 232 ERA+) before injuries derailed the last portion of the deal (only 25 games played in 2021 and 2022). Yes, he walked a lot of batters in the Bronx, but the Yankees did well keeping a good player and a better person.

Happ is mostly remembered for the 2020 playoffs when the disgruntled lefty was brought in as a reliever and struggled in a playoff loss. And Happ did not perform in 2019 (4.91 ERA, 5.22 FIP). Even after a solid 2020, the lows are harsh with Happ. The Yankees probably would’ve been better off letting Happ sign elsewhere after 2018.

2020: Gerrit Cole Joins the Yankees (9 years, $324 million)

Results: So far, so good. Yes, Cole gives up a lot of home runs and he has had his struggles at times in the regular season and in one playoff start against the Red Sox (also, against Rafael Devers, but so does most of the league). Still, Cole has been a reliable, number-one starting pitcher for the Yankees and has had his fair share of big performances, like saving the Yankees in the 2022 division series and everything in 2023. He is being paid a lot, but I’m calling this one a win.

2021: D.J. LeMahieu resigns with the Yankees (6 years, $90 million)

Results: There’s still time, but LeMahieu has been nowhere near the MVP-level player he was in his first two seasons as a Yankee. He’s tried to play through some injuries and that’s cost him his power (xSLG no higher than .403 over the last three seasons vs. a low xSLG of .460 in his first two) and now he’s 35 years old. There’s still time for LeMahieu to at least get some of his bat back and he’s had stretches of being a quality hitter, not to mention he can still pick it around the infield. But, the first half of his deal is not looking great.

2023: Yankees Resign Aaron Judge (9 years, $360 million), Anthony Rizzo (2 years, $40 million, option for 2025), sign Carlos Rodón (6 years, 162 million)

One year is not enough time to properly re-evaluate long-term deals, but it isn’t great that only one of these players had an elite year. The Yankees had to keep Judge and Rizzo for the current contending timeline and future. If only Judge hadn’t injured his toe in Dodger Stadium, he could have pushed his personal home run record, but 37 home runs in 106 games is ridiculous. Rizzo looked to have a solid season until he collided with Fernando Tatis Jr. at first base and then played through what turned out to be a concussion. Hopefully, he can regain his April-May form. Rodón was a surprising move for Cashman; rarely does he take a risk on players with this type of injury history. And he only made it through 14 starts because of injury but those 14 starts were brutal. I’ll reassess after next season, but not a good start for Rodón.

What to Make of these Moves:

Cashman has had some willingness to pay for position players, but most of these big moves outside of the organization centered around pitching and defense. Ellsbury, McCann, and even LeMahieu all had high defensive pedigrees, but the Yankees overlooked their ages and got inconsistent hitters. And the lack of impact-bat signings loom large. Canó, Bryce Harper, Corey Seager, and more all could have been part of the Yankees’ long-term future but the team decided to go in another direction. Yes, the lineup had a great three-year stretch from 2017-2019, but aside from that, this team has not hit and they’ve lacked impact lefties that playoff Yankees Stadium. And some failed trades that will be discussed later have impacted that, but imagine if the Yankees had Harper doing what he’s done in Philadelphia in New York?

The Yankees have gone after some big names in the pitching field, again, leaning towards veterans. Cole is probably the only outright win, although Tanaka and Britton both provided quality depth and, as frustrating as he could be, Chapman was at least an above-average regular season closer. Still, the success rate is not high enough for Cashman to take major credit for his pitching moves. And again, for the Yankees to make it back to the World Series, they have to bring in impact bats available in the future.

What are your thoughts on Cashman’s work with larger contracts over the last decade? This is far from an exhaustive list, if you have any thoughts on other signings or extensions I missed, feel free to add them in the comments below. And I’ll have more thoughts on the Yankees’ recent trades under Cashman later this month.


Alan B.
Alan B.
Oct 08, 2023

His mistake was trading away McCann, 'being nice' to him when do it. Why does he have to be nice to a veteran doing stuff like that when he grinds prospects down? McCann should've been the primary DH in 2017, and backup to Sanchez. Jose Guzman went to the Marlins in the Stanton deal, where Abreu couldn't stay healthy in 2017-18, but he kept his prospect rank, then never was converted in the minors to a reliever. But Cashman & his gang love him. Why? How? Whst has the supposedly incomparable Matt Blake done with him?


Oct 08, 2023

during these "lost" years, Cashman has extended his authority in the Yankee organization to include supervision of the minor league system.

he seems to have a good handle on prioritizing the acquisition and development of players for the organization that is, by rule, usually denied access to the most desired US/American amateur players.

Alan B.
Alan B.
Oct 10, 2023
Replying to

We get talented guys in the draft. Do we get Top 10 guys? No. But when you can churn out prospect after prospect. I mean just look at this year's FCL team. 5 of the 8 position players are Yankees, Thorpe was the MiLB Pitcher of the year. Look at what Jesus Rodriguez has done this year after escaping years of rookie ball. But why do most of these guys fail? It's gotta be based in the coaching these kids get.


Van Oliver
Van Oliver
Oct 08, 2023

”rarely does he take a risk on players with this type of injury history.” - Have you not been watching the Yankees the past decade? This is actually Cashman’s MO. You only need to go back to this past April when EVERY SINGLE ONE of Cashman’s major acquisitions over the prior 24 months was one the DL...

From Ellsbury to Hicks, to Stanton, to Bader (who was on the DL when they f’n acquired him), had injury histories. Let’s not even get into Montas. The Yankees injury woes have been too Consistent, too Copious, and too Continuous to be a coincidence.

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