What’s next for the Yankees?Aaron Judge Aaron Boone’s future uncertain on three key questions after sweep

At some point during the 2022 season, the New York Yankees appear to have a chance to challenge MLB’s 116-win record. In the end, they were unceremoniously swept by the Houston Astros in the ALCS, A series that exposed the gap between the two teams. Houston sent the Yankees home 6-5 on Sunday night. This is the third time the Astros have eliminated the Yankees in the past six seasons.

The Yankees haven’t won a World Series since 2009, a drought that’s been eternity in the Yankees’ years, and they’ve repeatedly stalled in what we call the Aaron Judge era of the playoffs. Since Judge’s AL Rookie of the Year season in 2017, the Yankees have lost in the ALCS three times (2017, 2019, 2022), the ALDS twice (2018, 2020) and the wild card once (2021) game. So far, the group peaked with a loss to (who else?) the Astros in Game 7 of the 2017 ALCS.

Now Judge is a few weeks away from free agency, Gerrit Cole and Giancarlo Stanton are still a year away from their prime, while others like Josh Donaldson and DJ LeMahieu don’t look like much. Likely to be a major contributor to the championship team going forward. The Yankees are still a very good team — it’s no accident that you win 99 games — but we’d love to know if the best days for this franchise are over and where the next core will come from.

Here are three pressing questions for the Yankees heading into one of the most important offseasons of the past 25-30 years. Maybe even longer than that.

1. Will they keep the judges?

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The problem is that the Yankees can’t keep Judge, the 62-homer. Of course they can. They’re the Yankees, and they can match — and beat — any contract offer made this offseason. It would be foolish to pretend otherwise. All indications are that Judge wants to stay on with the Yankees, and the Yankees want to keep Judge, though saying and doing are different things. Complicated contract negotiations are underway, and the Yankees, led by Hal Steinbrenner, have kept a restricted card on their payroll.

“There’s a pot of gold in there. It’s not determined what the gold is – how much it weighs – but it’s a pot of gold, no doubt about it. It’s great for him. It’s already a big pot, obviously, it will Bigger,” general manager Brian Cashman told The Associated Press about Judge’s impending free agency ahead of the ALDS. “He put himself in an amazing position with a lot of options. Obviously, obviously, we want to win in that discussion, which is obviously another day. But we said it before the season. We said the season Many times. If you need to hear it again. I’ll say it again: Yes, of course we would love to have Aaron Judge back with the New York Yankees, but that’s another day.”

Judge’s record season could result in a record contract for him, though breaking records for total guarantees (Mike Trout’s $426.5 million) and average annual value (Max Scherzer’s $43.3 million) would It’s difficult because the judge turns 31 shortly after opening day in 2023. That said, his next contract will be worth more than $300 million. Last month I estimated nine years and $38 million per year, or $342 million in total. Like I said, this is just a guess.

There’s no way to replace Judge, and losing him as a free agent would set the Yankees back completely. He’s their best and most marketable player, and the available replacements pale in comparison. In free agency, there’s Andrew Benintendi after wrist surgery, David Peralta, Brandon Nimoy, Jock Pederson, and that’s it. Judge is a 10.6-WAR player in 2022. Those four are worth a combined 10.1 WAR, and I wouldn’t be shocked if Judge beats them again in 2023.

Maybe Brian Reynolds could be pryed open in a trade, though that would require giving up the prospect the Yankees have so far been reluctant to trade (more on that later). Ian Happ? Anthony Santander? There is no substitute judge. The only way you can do it is to upgrade a few positions and replace him as a whole, which isn’t easy. The Yankees are the richest team in the sport. There’s no reason they couldn’t re-sign the judge. The only question is will they make every effort to re-sign him?

2. What about think tanks?

Cashman’s contract expires at the end of the season. Manager Aaron Boone is deftly thrown under the bus by some players after ALDS Game 3 loss. Between wages and competitive balance taxes, the Yankees trail the New York Mets this year by more than $50 million. Why are the Yankees making $50 million more than any team, let alone a team in their city? The general manager is not signed, the manager may have lost the clubhouse, and the owner’s commitment to sending the best team is in question. There are real problems to be solved here.

My hunch — and I stress it’s just a hunch — that the Yankees will keep Cashman. The owner loves him because the Yankees play in the playoffs every year while abiding by the rules of the payroll, whatever it is. The Yankees are not a “World Series or bust” team under Hallstein Brenner, they are under George. They can openly say whatever they want. Their actions show a team prioritizing enough to make the playoffs and not more, and it would be great if they had a championship during those years. Otherwise the playoffs are too unpredictable to be hung up on by the outcome of the short series.

Boone’s state is harder to predict. He was awarded a new three-year deal last offseason, making him the first manager in franchise history to return for a fifth season after failing to win a World Series in the previous four years. Several players, notably All-Star Clay Holmes and Game 3 starter Luis Severino, questioned Boone’s decision-making in the ALDS, a huge red flag. It takes a lot — a lot — for players to get to the point where they openly question managers.

Ownership isn’t going away, and the Steinbrenners haven’t given anyone much reason to believe they’ll raise the payroll to the Mets/Dodgers level, which means over $300 million. If there are any major changes this offseason, it’s more likely that Cashman and/or Boone will be replaced than more money being pumped into the roster. At the end of the day, the Yankees were interrupted again by the Astros. That’s happened enough time to force a change, and the conditions this offseason (Cashman’s contract expired and Boone was questioned by his players) are ripe for change.

3. How did the Yankees improve?

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It’s hard to improve a 99-win roster, but with that said, the 2022 Yankees are more of a true 93-94-win team, improving to 99 wins in Judge’s historic season. There were a couple of games this season, especially in the second half, where Judge led the Yankees to victory even though they were thoroughly beaten. The judge was fourth in the AL MVP voting a year ago. If the Yankees got the 2021 judge in 2022 instead of the judge they got, the AL East game would be much closer.

Despite their talent, the Yankees have clear areas for improvement, and losing Judge to free agency will only add to the offseason to-do list. Most notably, the Yankees have to do something about shortstop. They gave up last offseason’s historic free agency class and selected Isiah Kiner-Falefa, a lightweight bat that largely negated him in terms of finishing the game impressively range. He is prone to errors, He lost his job in the playoffs. How did it get to this point in October?

The Yankees waived those free agents because (in order) they didn’t want to give out a big contract, and they wanted top shortstop prospects Oswald Peraza and Anthony Volpe to keep that spot in the future. Volpe had a very good season in Double-A and finished the year in Triple-A. Peraza was great in Triple-A, where he spent September in the Bronx, even though he only started 14 games. He hit .306/.404/.429 in limited action and impressed defensively, but was left out of the ALDS roster.

If the Yankees sign a big contract this offseason, it’s going to the judges, not Carlos Correa or Trea Turner or one of the other elite shortstops. In that case, will Kiner-Falefa get the job again in 2022? Will the Yankees give it to Perazza? Did they jump Volpe straight into the majors on Opening Day like the Astros did with Jeremy Peña? Shortstop is an obvious position to upgrade. The same goes for third base, with Donaldson showing off his age, left field, rotation and bullpen in 2022.

It should be noted that the Yankees have made a lot of money off the books this offseason, and most of that has been spent on players who don’t contribute much in 2022. Here are the upcoming free agents who are with the Yankees all season 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 whether he will actually opt out.)

Judges are clearly big names, and Taillon is a solid mid-round pick that must be replaced. The Yankees have $36.63 million tied to four relievers who haven’t done much this year. Britton and Green missed most of the year recovering from Tommy John surgery, and Chapman pitched poorly when healthy (then give up in the playoffs), while Castro was mysterious about the shoulder injury. That $36.62 million only won 81 innings and lost 0.5 WAR.

The Yankees revamped their lineup last offseason to improve their defense and add more touch bats to the lineup, and overall it worked. They’ve scored very well on the defensive end, and their strikeout rate of 22.5 percent is near league average (22.4 percent). Now they have to re-sign officiating, fill the void in left field, look for upgrades on the left side of the infield, and strengthen the pitching staff. There is some money to spend and room for improvement. Ultimately, it comes down to the judge. The Yankees could be handcuffed until they know the judge’s decision. He holds the keys to their offseason.

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