Contemplating a Yankees Shakeup in the Wake of the Astros’ Sweep

© Vincent Carchietta-USA TODAY Sports

With a routine 73-mph comebacker off the bat of Aaron Judge, the Yankees’ season ended not with a bang but a whimper as the Astros completed their ALCS sweep to advance to the World Series for the second straight season, their third out of the last four, and their fourth out of six. Though two of this year’s ALCS games were decided by one run and another by two, the final result — the Yankees’ first time being swept out of a series since the 2012 ALCS — was a lopsided one, and it had an all-too-familiar feel.

Indeed, the Yankees have set a record by losing in five straight ALCS appearances (2010 by the Rangers, ’12 by the Tigers, ’17, ’19 and this year by the Astros). Including their 2015 AL Wild Card Game loss to the Astros, they’ve been bounced by Houston in four straight postseason meetings, an imbalance not unlike their own recent dominance of the A’s and Twins:

Back in July, Yankees manager Aaron Boone spoke of the need for his team to surmount the Astros, saying, “Ultimately, we may have to slay the dragon, right?… The narrative’s not to going to change until you beat them in the playoffs, if that day comes.” But with another series loss, their season has ended in disappointment. Even if it’s by way of a short series — one of just four (out of 10) in which the team with the better regular season record triumphed — it’s a blow that has sent the Yankees reeling.

A season with 99 wins, an AL East title, and a Division Series victory shouldn’t be regarded as a failure, but in the Yankees’ universe, it so often is, if not by the organization then by fans and tabloid-minded pundits. All too many from both camps long for the drama of the George Steinbrenner era, when a bad streak could cost a manager or general manager his job or send a player back to Triple-A. They’re used to a bullying owner driven by emotion rather than reason and careful planning, as if yielding to those baser impulses wasn’t a major factor in the team’s 1979-95 championship drought, their longest since Babe Ruth hit the Bronx. The patience that yielded the success of the Joe Torre era and its four championships is nowhere in evidence.

That son Hal Steinbrenner, the current managing general partner, is rational where his father was impulsive drives such people batty, particularly when he publicly reasserts his commitment “to do everything we’re able to do to field a championship caliber team and try to win a World Series,” as he did in March. Critics can rightly point to the fact that the Yankees were outspent by the Mets and Dodgers by tens of millions of dollars, though their $249 million payroll ($264 million for tax purposes) wasn’t enough to get them past the Astros, who “only” spent $179 million. Not all of the Yankees’ money was well spent. For example, they received -0.2 WAR for Aroldis Chapman’s $16 million, 1.6 WAR for Josh Donaldson’s $23.75 million and 1.2 WAR for Giancarlo Stanton’s $29 million. Yet the ability to run a high payroll doesn’t mean hitting on every expenditure to justify it, it means not being sunk when some of those moves — such as Chapman’s collapse — don’t pan out.

As the Yankees haven’t won a World Series since 2009, and now seem to be further behind the Astros than they were three years ago, it’s fair to wonder just how much change is needed, and what the organization’s options are. That goes not just for their quest to retain Judge following his historic 62-homer, 11.5 WAR season, but for the leadership driving that effort. They do appear to have an opening to make a change, as senior vice president and general manager Brian Cashman — who’s been in place since 1998, overseeing four champions and six pennant winners — is a pending free agent. Thus far, it certainly hasn’t sounded as though Cashman was on the hot seat, not when multiple reports have pointed to his return. A change at the top would require some soul-searching from Steinbrenner, and if undertaken at this late stage would probably place the Yankees at a disadvantage for the offseason, since it’s not like the incoming GM or president of baseball operations would be in place before the start of free agency; prospective free agents might look at the disarray and choose to go elsewhere. The timeline of the Red Sox-Dave Dombrowski relationship is instructive; he was fired in September 2019 and Chaim Bloom was hired a month later. The Mets didn’t hire Billy Eppler until late November of last year, but they had team president Sandy Alderson above him to help lay the groundwork for the offseason, where the Yankees don’t have anyone on the baseball side above Cashman. The point is that such moves are generally made with much longer lead times, not when emotions are running high after elimination from the playoffs.

While he’s made his mistakes with the Yankees’ roster, Cashman has had some impressive recent successes as well. The trade that brought Joey Gallo from Texas last year might have been an utter flop, but the one that brought Donaldson and Isiah Kiner-Falefa in exchange for Gary Sánchez and Gio Urshela at least upgraded the defense on the left side of the infield, albeit at the expense of offense. Moving on from Sánchez to Jose Trevino (who cost just a low-level arm and a reliever, Albert Abreu, whom they later reclaimed on waivers) was a significant success; Trevino made the All-Star team, and his 3.7 WAR was the team’s best from its starting catcher since Sánchez in 2018. The Jordan Montgomery/Harrison Bader deal initially looked catastrophic, but Bader’s five home runs in the postseason made him the offense’s unlikely centerpiece and a fan favorite. Anthony Rizzo and DJ LeMahieu more than justified their modest free agent salaries, while low-cost acquisitions brought the Yankees All-Stars in Nestor Cortes (a minor league free agent in 2021) and Clay Holmes (a trade acquisition in mid-2021), and key contributors in Wandy Peralta (acquired for Mike Tauchman) and Matt Carpenter (a minor league free agent). While the talent pipeline didn’t yield many players whose first contributions came this year, the system did produce Judge and Luis Severino, both with multiple All-Star appearances, on Cashman’s watch, and he used Montgomery, another homegrown player, to acquire Bader, his new center fielder.

If the Yankees let Cashman go, they could try to woo Theo Epstein, who has presided over championships with the Red Sox and Cubs, in case you haven’t heard. Currently working for the commissioner’s office, he bypassed an opportunity to become the Mets’ president of baseball operations last year. Hiring Epstein wouldn’t require the delicate dance of pursuing an executive employed by another team, such as the Brewers’ David Stearns or even the A’s Billy Beane, both under contract through at least next year; neither of those teams is likely to grant the Yankees permission to interview anyway. Even if they did, could either of that duo thrive under the conditions that Cashman has? It’s no guarantee. Likewise when banking on an up-and-comer, such as the Marlins’ Kim Ng, a former Yankees assistant GM who is no longer surrounded by allies from the Bronx, from Derek Jeter above her to Don Mattingly below. The Astros’ James Click doesn’t even have a contract for next year yet, but it’s doubtful Jim Crane lets him get close to the Yankees. The most likely route for change might be an internal promotion for VP of baseball operations Tim Naehring, who has declined interviews for other openings but has drawn comparisons to organizational godfather Gene Michael, or VP of domestic amateur scouting Damon Oppenheimer, who has interviewed elsewhere.

If Cashman does stay, is it time for Boone to go? Hired without managerial experience at any level, he’s posted a .603 winning percentage (a 98-win clip) with five straight trips to the postseason, but only twice in that span have the Yankees won the division. Boone has done a very good job of navigating through the long season with squads that have often been beset by injuries, but he struggled to arrest the team’s midseason free fall this year, and for all of his touted communication skills, a breakdown with Holmes over the righty’s availability in Game 3 of the Division Series led to both Holmes and Severino publicly questioning what was going on. At times during the ALDS and ALCS, Boone called upon lower-leverage relievers such as Montas and Clarke Schmidt (who took the loss in ALDS Game 3), then watched his choices backfire. Even when his choices made sense, such as going to Lou Trivino — adept at getting both grounders and strikeouts — with the bases loaded, nobody out, and three straight righties coming up in ALCS Game 3, they sometimes failed. The public judges managers on outcomes, not processes, and when it came to Boone’s bullpen, the bad outcomes were both costly and all too visible, making him a lightning rod for criticism.

And then there was the shortstop situation, where Kiner-Falefa wore out his welcome due to his defensive mistakes, riding the pine in the last two games of the ALDS and starting just two of four ALCS games, with rookies Oswaldo Cabrera and Oswald Peraza each making starts as well. Throughout both series, the shortstops, Donaldson, and the left fielders often struggled with balls hit into shallow left, with Hicks suffering a season-ending injury in a collision with Cabrera and a couple of other balls dropping for base hits at inopportune times. When Kiner-Falefa returned to shortstop in the ALCS finale, he was part of a botched double play attempt on a Jeremy Peña grounder in the seventh inning; Gleyber Torres was charged with the error, but Kiner-Falefa’s route to the bag was questionable, and the misplay loomed large in the two-run rally that cost the Yankees their lead and, ultimately, sent them into the winter. Boone defended his lineup choices throughout, but the instability couldn’t have helped, and in the bigger picture, the thin ice that Kiner-Falefa crashed through points to a disconnect between the front office and the dugout that resulted in Peraza getting only 14 games of regular season experience.

If Boone, who is under contract though 2024, is fired and Cashman stays, it’s difficult to see the GM bringing in a high-profile veteran manager such as Joe Maddon. Yes, Maddon won a World Series and a couple of pennants with analytically-minded organizations in Tampa Bay and Chicago, but he’s lately been vocal about losing his authority in Anaheim, taking up a reactionary position within the sport’s endless culture war, and so a fit seems unlikely in the Bronx. Mattingly, long a fan favorite, would certainly be a popular choice, and he’s had some success since Cashman chose Joe Girardi over him in 2007, winning three straight division titles with the Dodgers and taking the Marlins to their first postseason since 2003. Yet he and Dodgers president of baseball operations Andrew Freidman couldn’t find the same page when his contract was up following the 2015 season, and the Dodgers have since been even more successful with Dave Roberts. If you’re imagining Cashman being replaced by an executive who’s even more forward-thinking, it’s hard to see either Maddon or Mattingly meshing with such a unicorn.

If Cashman is choosing another manager, he could look to Hensley Meulens or Carlos Beltrán, former Yankees who both spent the past year serving the organization, the former as assistant hitting coach, the latter as a YES Network analyst. Meulens was a finalist when Boone was hired in 2017, and served as the Giants’ hitting coach when they won three titles under Bruce Bochy and as the Mets’ bench coach under Luis Rojas in ’20. Beltrán was hired to manage the Mets in late 2019, but was forced to resign just two and a half months later due to the findings of commissioner Rob Manfred’s investigation into the Astros’ illegal sign stealing. If Alex Cora and A.J. Hinch could get managing jobs after serving year-long suspensions for roles in sign-stealing schemes, Beltrán’s role in that mess shouldn’t disqualify him. Rojas, who spent the past season as the Yankees’ third base coach could be a candidate himself, but he might be a tougher sell after his .464 winning percentage in Queens.

Finally there’s the roster, and the decisions don’t get much bigger than whether to re-sign Judge to the massive deal he’s earned after setting an AL record with 62 homers and nearly winning the Triple Crown. Dan Szymborski estimated a contract in the $270 million to $290 million range based upon his ZiPS projections, and the general industry assumption is that he could push $300 million. And no, the decision should not hinge on his .139/.184/.306 postseason line or his 1-for-16 against the Astros. Judge has had big moments in the postseason before as well as bad ones; it was just a week ago he set a record with his fourth career homer in an elimination game.

The Yankee love Judge’s temperament and presence, seeing him in the Mattingly-Jeter mold, but for as much as Judge “wants to be a Yankee for life,” as he said in the spring, a return is hardly guaranteed. He grew up near the Bay Area, and within the industry, the Giants are believed to be his most likely destination outside the Bronx. That said, MLB.com’s Mark Feinsand reported on Monday that Mookie Betts is willing to move from right field to second base as the Dodgers, who have around $100 million coming off the books, consider making a run at Judge; it might be a decoy, as they have a hole at shortstop with Trea Turner hitting free agency, but then again, it might not be. And with Steve Cohen determined to use his financial might, the Mets are a real threat as well; the public relations damage of losing Judge to the crosstown rivals would obviously be immense.

That said, a pursuit of one of the market’s top shortstops in Carlos Correa (who just turned 28) or Turner (who turns 30 next June 30) could make more sense given Judge’s age (31 next April 26) and the limitations of his position. At the very least, signing one of them could save face if the slugger chooses a different destination. The Yankees have stayed out of the high-end infielder market in recent years due to their belief in prospects Peraza and Anthony Volpe, but third and second base will need new talent sooner or later, and the pair could fit into such an infield. Signing a marquee shortstop could also open the door to trading Torres, who restored some value to his stock and still has two years before free agency.

Beyond Judge, the most notable of the Yankees’ eight other free agents are Jameson Taillon and Andrew Benintendi, along with Chapman (who’s burned his last bridge in the organization), Zack Britton, and Chad Green (who’s recovering from Tommy John surgery). They’ll likely have to deal with Rizzo opting out of the second year of his deal, though it’s not hard to see them working to retain him. Finding somewhere to offload the unpopular Donaldson and eating some of his remaining $29 million would seem to be another high priority.

Space prevents me from poring over the roster further but suffice it to say that whoever is in charge has their work cut out for them. Particularly if Judge departs, the roster could look very different in 2023. Whether that work will be undertaken by somebody besides Cashman, with somebody besides Boone assembling the pieces next season, remains to be seen, but for all of this rumination, at the moment there’s little indication that an organization-wide shakeup is coming.





Brooklyn-based Jay Jaffe is a senior writer for FanGraphs, the author of The Cooperstown Casebook (Thomas Dunne Books, 2017) and the creator of the JAWS (Jaffe WAR Score) metric for Hall of Fame analysis. He founded the Futility Infielder website (2001), was a columnist for Baseball Prospectus (2005-2012) and a contributing writer for Sports Illustrated (2012-2018). He has been a recurring guest on MLB Network and a member of the BBWAA since 2011. Follow him on Twitter @jay_jaffe... and Mastodon @jay_jaffe.

138 Comments
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Naked Mole Gaettimember
1 month ago

Paying $300 million for a 31-year-old RF — regardless of his historic platform season — seems unwise to me, but, based on reports, there are a few teams considering doing just that.

sadtrombonemember
1 month ago

As awesome as he was this year, I tend to agree with you. But it seems almost a lock that it will happen.

Also, although I think it’s crazy, I do think that the Yankees probably should do it if that’s what it takes. I can’t say that for any other team, but he has more value to them after this historic year than to anyone else.

Last edited 1 month ago by sadtrombone
Dooduh
1 month ago
Reply to  sadtrombone

The Yanks will have $100M tied up in 3 players.. the only team with 3 $30M+ annual salaries I believe.

sogoodlooking
1 month ago
Reply to  Dooduh

Imagine that bunch in 2025, at 33, 34, and 35 years old, when the Yankees will also have another $25m tied up in a 36yo and 35yo DJLM and Hicks.

Or 2027, when the big three are 35, 36, and 37, projecting to something like 5 wins?

RoyalsFan#14321member
1 month ago
Reply to  Dooduh

The Mets will join that list (3 $30M+) this offseason.

Dooduh
1 month ago

Mets were there already.

But Jake seems likely to leave. Mets may redeploy those funds into another big contract tho.

Last edited 1 month ago by Dooduh
baubo
1 month ago

I think if you believe he can have another 3-4 seasons at about 80% of his 2022 season, and then an average to above average production for another 2-3 seasons, that should make it worth about $300mil. Especially if there is a lot of deferrement involved.

To me though his postseason history does deserve scrutiny though. He has overall been mediocre in the postseason, with success generally more towards earlier in his career. Teams would know a lot about this than me, but there is a chance he is being more figured out by better teams. The Astros pitchers have gone after him the entire series in a way you don’t expect for supposed most feared hitter in baseball

Jimmember
1 month ago

The Giants won’t pay Judge that much. They are too smart.

sadtrombonemember
1 month ago
Reply to  Jim

I keep seeing things about the Dodgers and the Giants and I just don’t know that I buy it.

I still think it’s probably the Mets or the Yankees.

fjtorres
1 month ago
Reply to  sadtrombone

Maybe the SF/LA teams want to drive the Judge market higher to reduce the competition for the guys they *do* want? 😇

hittfamily
1 month ago
Reply to  sadtrombone

What if the Marlins Jose Reyes/Mark Buehrle him out of nowhere, like they did a decade ago. No state income tax in FL.

bl0ckymember
1 month ago
Reply to  Jim

Giants have been bargain hunting for a number of offseasons now. It’s time to pay up, the fans are restless

sadtrombonemember
1 month ago
Reply to  bl0cky

Watch for Ohtani.

Lanidrac
1 month ago

What if it was just a 7-year contract where you paid him $45M for each of the first 5 years, $40M in Year 6, and $35M in Year 7?

Mac Quinnmember
1 month ago
Reply to  Lanidrac

Hal cares more about the luxury tax, which is calculated on AAV. This isn’t the NBA where you can do descending salary structures to duck under the cap.

Rex Manning Daymember
1 month ago
Reply to  Lanidrac

The actual salary for a given year doesn’t matter to the Yankees. They only care about the luxury tax hit, which is the average salary across the entire contract.

MikeSmember
1 month ago

I’d say that whoever signs him for that much is probably only counting on a few good years, and hoping for good health which he didn’t have in 2018 – 20. The contract may be for 7 or 8 years, but that’s just to reduce the AAV and avoid the CBT, not because they believe he will be a five win player at 39.

It is risky because there isn’t a lot of recent success for guys that age. Not a lot of guys are aging as well as some superstars were 10 or 15 years ago AND he has a history of injury. Near as I can tell, there have only been 3 5 win seasons (2 by Beltre, one by Werth) and a handful of 4 win seasons posted by guys 35 or older since 2010. Unless he is going to be a hitter version of Verlander or something, you know you are going to be overpaying on the back end.

sbf21member
1 month ago

The calculus for Judge, especially in relation to the NYY, is different than for almost every other player in the sport. In addition to the substantial game value that he provides, AJ puts tens of millions of dollars into the coffers of the Steinbrenner family thru ticket and concession sales (via refreshments, shirts and other memorabilia) along with much higher viewership of the YES network. The only other person who could match what Judge brings is probably Ohtani.

He’s easily worth $300M to them. I’m guessing $304/8 yrs – $38M AAV.

fjtorres
1 month ago
Reply to  sbf21

Don’t forget merchandising.

GFEmember
1 month ago
Reply to  fjtorres

I think merchandise sales are pooled and shared equally by all 30 teams.

Antonio Bananasmember
1 month ago
Reply to  sbf21

I mean sure, but does that hold up in 2025-2030 after he only manages 400 AB in 2023 & 2024, 35ish HR each, then settles in as a 2-3 WAR guy?

At one point in time Shopify stock made me a bunch of money, now? Wish I had dumped it.

sbf21member
1 month ago

lol re: Shopify. I bought it at $137 pre-split. Sold 1/3 at $275 after it doubled. Sold another batch at $364 and unload the rest when it broke over $400. Then beat myself up for over a year as it soared to over $1600 a share. Now I don’t feel so bad.

Ivan_Grushenkomember
1 month ago

DC projects him at 7 WAR. It would take a cratering very soon to make him useless before the 5th year. Possible but he seems as good a bet as Turner.

fuster
1 month ago

penny wise and pound foolish.

Judge has been the most valuable Yankee since Mickey Mantle.

if you wish to save the money, explain how you would replace his value