At one point in the 2022 regular season, the New York Yankees looked like they had a chance to challenge the MLB record of 116 wins. In the end, they were swept unceremoniously by the Houston Astros in the ALCS, a series that revealed the gap between the two teams. Houston sent the Yankees home Sunday night with a 6-5 win. It’s the third time in the past six seasons that the Astros have eliminated the Yankees.
The Yankees haven’t won a World Series since 2009, a drought that qualifies as an eternity in Yankee years, and they repeatedly stalled in the playoffs during what we’ll call the Aaron Judge era. Since Judge’s AL Rookie of the Year season in 2017, the Yankees have lost three times in the ALCS (2017, 2019, 2022), twice in the ALDS (2018, 2020) and once in the Wild Card Game. (2021). To date, that group culminated in a Game 7 loss to (who else?) the Astros in the 2017 ALCS.
Now Judge is weeks away from free agency, Gerrit Cole and Giancarlo Stanton have had another year chipped away from whatever remains of their bounties, and others like Josh Donaldson and DJ LeMahieu look less likely to be major contributors for a championship team in the future. The Yankees are still a great team – you don’t win 99 games by accident – but it’s fair to wonder if this group’s best days are behind them and where the next core is coming from.
Here are three pressing questions facing the Yankees as they head into one of their most important offseasons in the past 25 to 30 years. Maybe even longer than that.
1. Will they keep the judge?
The question isn’t whether the Yankees can keep Judge, the 62 homer. Of course they can. It’s the Yankees and they can match — and beat — any contract offer that comes their way this offseason. To claim otherwise is folly. Everything points to Judge wanting to stay a Yankee and the Yankees wanting to keep Judge, although saying and doing are different things. A complex contract negotiation is underway and the Yankees have retained a restriction plate on their payroll under Hal Steinbrenner.
“There is a pot of gold there. It remains to be determined what the gold – how much it weighs – but it is a pot of gold, without a doubt. So good for him. It was already a big pot and obviously it’s going to be bigger,” general manager Brian Cashman told The Associated Press of Judge’s upcoming free agency ahead of the ALDS. “He’s put himself in an incredible position to have a lot of choices. And clearly, obviously we’d like to win the day on that discussion, and that’s obviously for another day. But we said that before the season. We’ve said that many times over the course of the season. If you ever need to hear it again. I’ll say it again: yes, sure, we love seeing Aaron Judge again as the New York Yankee, but that’s it. for another day.”
Judge’s record-breaking season is potentially setting him up for a record deal, though breaking the records for total collateral ($426.5 million from Mike Trout) and average annual value ($43.3 million from Max Scherzer) will be tough as Judge turns 31 shortly after opening day. 2023. That said, his next deal will be over $300 million. I estimated nine years and $38 million a year, or $342 million in total, last month. Like I said, that was just a guess.
There’s no way to replace Judge and losing him to free agency would set the Yankees back tremendously. He is their best and most marketable player, and the available replacements pale in comparison. In free agency, there’s post-wrist surgery Andrew Benintendi, David Peralta, Brandon Nimmo, Joc Pederson, and that’s really it. Judge was a 10.6-WAR player in 2022. Those four were worth 10.1 WAR combined, and it wouldn’t shock me if Judge surpassed them again in 2023.
Maybe Bryan Reynolds can be released in a trade, although that would require giving up prospects the Yankees have so far refused to trade (more on them in a moment). Ian Happ? Anthony Santander? There is no substitute judge. The only way to do that is to upgrade multiple posts and replace it globally, and that’s not easy. The Yankees are the richest team in the sport. There’s no reason they can’t afford to re-sign Judge. The only question is will they do what it takes to re-sign him?
2. What about the brain trust?
Cashman’s contract is up after this season. Manager Aaron Boone was subtly thrown under the bus by a few players after the ALDS Game 3 loss. Between payroll and competitive balance tax owed, the Yankees were more than $50 million behind the New York Mets this year. Why are the Yankees being spent $50 million by any team, let alone a team in their own city? The general manager is unsigned, the manager may have lost the clubhouse, and the owner’s commitment to fielding the best team possible is in question. There are real issues to be addressed here.
My hunch — and I stress it’s just a hunch — is that the Yankees will keep Cashman. Ownership loves it because the Yankees make it to the playoffs every year while meeting the payroll mandate, whatever it is. The Yankees aren’t the “World Series or bust” team under Hal Steinbrenner that they were under George. They can say publicly what they want. Their actions indicate that a team that prioritizes being good enough to make the playoffs and not much more, and if they run into a championship one of those years, great. Otherwise, the playoffs are too unpredictable to cling to the outcome of a short series.
Boone’s status is harder to predict. He received a new three-year contract last offseason, making him the first manager in franchise history to return for a fifth season after failing to win a World Series in his first four years. The fact that several players, including near All-Star Clay Holmes and Game 3 starter Luis Severino, have questioned Boone’s decision-making in the ALDS is a giant red flag. It takes a lot – A LOT – for players to get to the point where they publicly question the manager like that.
The ownership isn’t going anywhere, and the Steinbrenners haven’t given anyone much reason to believe they’ll move the payroll to the Mets/Dodgers level, which means over $300 million. If a big change is made this offseason, Cashman and/or Boone are more likely to be replaced than more money pumped into the roster. Bottom line, the Yankees have just been blown by the Astros again. It’s happened enough times to force change, and the terms this offseason (Cashman’s contract is up, Boone is being questioned by his players) are ripe for change to happen.
3. How are the Yankees improving?
It’s hard to improve on a 99-win list, but that said, the 2022 Yankees looked more like a true 93-94 talent team that was elevated to 99 wins by Judge’s historic season. There have been several games this season, especially in the second half, when Judge led the Yankees to wins even though they were heavily outplayed. Judge finished fourth in AL MVP voting a year ago. If the Yankees got the 2021 judge in 2022 rather than the judge they got, the AL East race would have been much closer.
As talented as they are, the Yankees have clear areas that need improvement, and losing Judge to free agency would only add to the to-do list in the offseason. Most notably, the Yankees need to do something about the shortstop. They passed on last offseason’s historic free agent class and settled for Isiah Kiner-Falefa, a lightweight bat who largely negates his impressive range with issues finishing plays. It is prone to errors, and he lost his job in the playoffs. How did we get here in October?
The Yankees passed on those free agents because (in order) they didn’t want to give away a big contract, and they want top shortstop prospects Oswald Peraza and Anthony Volpe to hold the position going forward. Volpe had a very strong season in Double-A and finished the year in Triple-A. Peraza was very good at Triple-A and spent September in the Bronx, despite only starting 14 games. He hit .306/.404/.429 in limited action and impressed defensively, but was dropped from the ALDS roster.
If the Yankees hand out a big contract this offseason, it will go to the judge, not Carlos Correa or Trea Turner or any of the other elite shortstops. In this case, will Kiner-Falefa find the position in 2022? Are the Yankees giving the floor to Peraza? Do they skip Volpe straight into the big leagues on Opening Day like the Astros did with Jeremy Peña? Shortstop is an obvious position that can be improved. The same goes for third base, where Donaldson showed his age in 2022, left field, rotation back and the bullpen.
It should be noted that the Yankees have a lot of money coming off the books this offseason, and much of it was going to players who didn’t contribute much in 2022. Here are the pending free agents who spent the entire season with the Yankees, and their 2022 salaries:
(First baseman Anthony Rizzo has a $16 million player option and can also become a free agent. He hasn’t indicated yet if he will actually retire.)
Judge is obviously the big name and Taillon was a solid mid-rotation option who needs replacing. The Yankees had $36.63 million tied up in four relievers who didn’t do much this year. Britton and Green missed most of the year with Tommy John’s surgical rehabilitation, Chapman pitched badly when healthy (then dropped the team in the playoffs), and Castro was enigmatic around a shoulder injury. That $36.62 million only earned 81 innings and less than 0.5 WAR.
Last offseason, the Yankees redid their roster to improve their defense and add more contact sticks to the roster, and overall it worked. They ranked very well defensively and their strikeout of 22.5% was almost exactly the league average (22.4%). Now they need to re-sign the judge, fill a void in left field, find improvements on the left side of the infield and bolster the pitching staff. There is money to spend and room to improve. In the end, it depends on the judge. The Yankees could be handcuffed a bit until they know the judge’s decision. He holds the keys to their offseason.
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