What’s next for the Yankees? Three key questions with futures of Aaron Judge, Aaron Boone uncertain after sweep – CBS Sports

What's next for the Yankees?  Three key questions with futures of Aaron Judge, Aaron Boone uncertain after sweep - CBS Sports

At one point this season the New York Yankees looked like they had a chance to challenge the MLB record of 116 wins. In the end, they were unceremoniously swept away by the Houston Astros in the ALCS, a series that exposed the gap between the two teams. Houston sent the Yankees home Sunday night with a 6-5 victory. It is the third time in the last six years that the Astros 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’ve stalled in the postseason several times during what we’ll call the Aaron Judge era. Since Judge’s 2017 AL Rookie of the Year season, the Yankees have lost in the ALCS three times (2017, 2019, 2022), the ALDS twice (2018, 2020), and the Wild Card Game once (2021). So far, this group has peaked with 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 cut away from whatever is left of their primes, and others like Josh Donaldson and DJ LeMahieu look less likely to be major contributors for a championship team moving forward. The Yankees are still a very good 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 enter one of their most important offseasons in the last 25-30 years. Maybe even longer than that.

1. Will they keep Judge?

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The question is not whether the Yankees can keep Judge, the 62-homer. Of course they can. They are the Yankees and they can match — and beat — any contract offer that comes his way this offseason. To pretend otherwise is folly. All indications are that Judge wants to remain a Yankee and the Yankees want to retain Judge, although saying and doing are different things. There is a complex contract negotiation underway and the Yankees have kept a cap plate on their payroll under Hal Steinbrenner.

“There’s a pot of gold there. It’s yet to be determined what the gold is — how much it weighs — but it’s a pot of gold, no doubt about it. So good for him. It was already a big pot and, obviously, it’s going to be more big,” GM Brian Cashman told the Associated Press about Judge’s upcoming free agency before the ALDS. “He’s put himself in a fantastic position to have a lot of options. And clearly, obviously, we’d like to win the day in that discussion, and that’s obviously for another day. But we said that before the season. We said that. many times during the season. If you need to hear it again. I’ll say it again: Yes, of course we love having Aaron Judge back as a New York Yankee, but that’s all for another day.”

Judge’s record season may set him up for a record contract, although beating out the total guarantee (Mike Trout’s $426.5 million) and average annual value (Max Scherzer’s $43.3 million) records will be difficult as Judge turns 31 shortly after Opening Day. 2023. That said, his next contract figures to come in north of $300 million. I figured nine years and $38 million a year, or $342 million total, last month. As I said though, that was just a guess.

There is 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 are post-wrist surgery Andrew Benintendi, David Peralta, Brandon Nimmo, Joc Pederson, and that’s true. 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 blew them out again in 2023.

Maybe Bryan Reynolds can be cut loose in a trade, although that would require giving up the prospects the Yankees have so far been unwilling to trade (more on them in a bit). Ian Happ? Anthony Santander? There is no substitute judge. The only way you can do it is by upgrading several positions and replacing him altogether, and that’s not easy. The Yankees are the richest team in sports. 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 brain trust?

Cashman’s contract is up after this season. Manager Aaron Boone was subtly thrown under the bus by some players following the Game 3 loss in the ALDS. 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 outspent to the tune of $50 million by any team, let alone a team in their own city? The GM is unsigned, the manager may have lost the clubhouse, and ownership’s commitment to fielding the best possible team is in question. There are real issues to deal with here.

My hunch — and I emphasize that this is just a hunch — is that the Yankees will retain Cashman. Ownership loves him because the Yankees go to the postseason every year while following the payroll mandate, whatever it is. The Yankees are not the “World Series or bust” team under Hal Steinbrenner that they were under George. They can say whatever they want in public. Their actions point to a team that prioritizes being good enough to make the postseason and not much else, and if they come across a championship one of these years, great. Otherwise the postseason is too unpredictable to disrupt the outcome of a short series.

Boone’s status is more difficult 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 within his first four years. The fact that several players, most notably All-Star closer Clay Holmes and Game 3 starter Luis Severino, 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 question the manager publicly like that.

Ownership isn’t going anywhere and the Steinbrenners haven’t given anyone much reason to believe they’ll move payroll to the Mets/Dodgers level, which means more than $300 million. If any significant change is made this offseason, it’s more likely that Cashman and/or Boone are replaced than more money is pumped into the roster. Bottom line, the Yankees just got gasped by the Astros again. There have been enough times to force change, and conditions 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?

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It’s hard to improve on a 99-win roster, but that said, the 2022 Yankees were more like a 93-94 win real talent team that was elevated to 99 wins by Judge’s historic season. There were several games this season, especially in the second half, when Judge took the Yankees to victories even though they were completely outplayed. Judge finished fourth in the AL MVP voting a year ago. If the Yankees get 2021 Judge in 2022 rather than the Judge they got, the AL East race would be 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 offseason to-do list. Most notably, the Yankees need to do something about shortstop. They passed on last offseason’s historic free agent class and settled for Isiah Kiner-Falefa, a light bat who largely negates his impressive range with issues completing games. He is prone to error, and he lost his job in the postseason. How did it get to that point in October?

The Yankees passed on those free agents because (okay) they didn’t want to give out a big contract, and they want top shortstop prospects Oswald Peraza and Anthony Volpe to hold the position up front. Volpe had a very good season in Double-A and finished the year in Triple-A. Peraza was very good in Triple-A and he spent September in the Bronx, although he only started 14 games. He hit .306/.404/.429 in limited action and impressed defensively, yet was left off the ALDS roster.

If the Yankees hand out a big contract this offseason, it will go to Judge, not Carlos Correa or Trea Turner or one of the other elite shortstops. In that case, does Kiner-Falefa get the job again in 2022? Do the Yankees pass it to Peraza? Do they jump Volpe straight to the big leagues on Opening Day like the Astros did with Jeremy Peña? Shortstop is an obvious position that can be upgraded. So can third base, where Donaldson has shown his age in 2022, left field, the back of the rotation and the bullpen.

It should be noted that the Yankees have a lot of money coming off the books this offseason, and a lot of it went to players who didn’t contribute much in 2022. Here are the soon-to-be 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 become a free agent as well. He has not yet indicated whether he will actually opt out.)

Judge is obviously the big name and Taillon was a solid mid-rotation option that needs to be replaced. The Yankees had $36.63 million tied up in four relievers who haven’t done much this year. Britton and Green missed most of the year with Tommy John surgery rehab, Chapman pitched poorly when healthy (and then abandoned the team in the postseason), and Castro was enigmatic about a shoulder injury. That $36.62 million netted just 81 innings and minus-0.5 WAR.

Last offseason the Yankees remade their roster to improve their defense and add more contact bats to the lineup, and overall it worked. They rated very well defensively and their 22.5 percent strikeout rate was almost exactly league average (22.4 percent). Now they must re-sign Judge, fill a void in left field, find upgrades on the left side of the infield and strengthen the pitching staff. There is some money to spend and room to improve. Ultimately, it comes down to Judge. The Yankees may be handcuffed a bit until they know Judge’s decision. He holds the keys to their offseason.

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