4 pressing questions for Yankees to answer before 2023

At one point this season, it looked like the New York Yankees might be able to beat the MLB record of 116 wins. In the end, the Houston Astros swept them in the ALCS, a series that showed how far apart the two teams were. With a 6-5 win on Sunday night, Houston sent the Yankees home. The Astros have gotten rid of the Yankees three times in the last six years.

The Yankees haven’t won a World Series since 2009, which is an eternity in Yankees years, and they’ve often stalled out in the playoffs throughout the Aaron Judge era. The Yankees are still a very talented club — you don’t win 99 games by chance — but it’s reasonable to ask whether this group’s greatest days are behind them, and where the next core will come from.

Here are four serious concerns that the Yankees must address as they enter one of their most significant offseasons in their last three decades.

#1. Will the Yankees let Aaron Judge go?

During spring training, the Yankees gave Aaron Judge a seven-year, $213.5 million contract extension. He turned it down, and then he went out and hit 62 home runs. Late in September, ESPN’s Kiley McDaniel asked some MLB insiders about the size of Judge’s next contract. The answers ranged from seven years and $259 million to ten years and $375 million.

Aaron Judge will be 31 years old next year, so there are worries that he will have a meltdown like Albert Pujols or Miguel Cabrera as he gets older. However, someone will pay him, and most people think that amount will reach $300 million.

Will the Yankees do it? It’s hard to imagine Judge in another uniform, but history shows that when players of Judge’s level become free agents, they almost always sign with another team. The Yankees have money to fend off any team if they are willing to do so. They may raise money from trading Chapman and Britton to fit Aaron Judge into their “budget.”

If Judge joins another team? Well, Aaron Hicks is still around, but now Harrison Bader plays center field instead of him. Cabrera could probably play left field, but he might not do well in right. By the way, Judge was worth about 80 runs more than the average hitter in 2022, so if the Yankees replaced him with an average hitter, they would lose about eight wins.

#2. Will Boone and Cashman stay?

Cashman’s deal ends at the end of this season. After losing Game 3 of the ALDS, a few players put Aaron Boone under the bus in a subtle way and even Michael Kay blasted him for his wrong decision. This year, the Yankees were more than $50 million behind the New York Mets in terms of payroll and taxes. Why is a team in the same city as the Yankees spending $50 million more than them? The GM hasn’t been hired yet, the manager may have lost the clubhouse, and it’s not clear if the owners will put together the best team possible.

Cashman’s owners love him because the Yankees make it to the playoffs every year while sticking to whatever the payroll rule is. Under Hal Steinbrenner, the Yankees are not the “World Series or bust” team that they were under George. They are free to say anything in public. Their actions show that they only care about being good enough to get into the playoffs. If they win a championship one of these years, that’s great. If not, the postseason is too unpredictable to let the result of a short series bother you.

Boone’s situation is harder to figure out. He got a new three-year contract during the offseason, making him the first manager in franchise history to come back for a fifth season after failing to win a World Series in his first four years. But his decisions have proved to be wrong. All-Star closer Clay Holmes and Game 3 starter Luis Severino publicly questioned Boone’s decisions in the ALDS.

#3. Will the Yankees allow kids to have more MLB?

Well-paid veterans failed to save the Yankees in the playoffs. But there are some young men who should be able to revamp the team and may bring them another championship. But it depends on if the Yankees keep the old horses or bring in the new ones.

Anthony Volpe: Thanks to his Double-A and Triple-A performance, Volpe shouldn’t have to wait longer.

Oswaldo Cabrera: The switch-hitter started as an infielder, but when Benintendi went down, he moved to left field. He did well with the Yankees. He has become a great asset for New York.

Oswaldo Peraza: In 18 games with the Yankees, he hit.306 and stole 33 bases. Peraza can emerge stronger with more MLB time.

Clarke Schmidt: When he was in the majors, the Yankees mostly used him as a reliever, which may be his best role given the injuries he has had in the minors.

Clayton Beeter: Acquired from the Dodgers in exchange for Gallo, he made 23 starts in the minors, throwing just 77 innings but striking out 129, so he could be promoted to the majors as a reliever.

Everson Pereira: Although he has just 29 games above Class A, the 21-year-old Venezuelan might force his way into the outfield picture in the second half.

#4. How to improve the performance?

It’s hard to improve on a team that has won 99 games, but the 2022 Yankees were more like a 93-94 win team with real talent that won 99 games because of Judge’s historic season. This season, especially in the second half, Judge helped the Yankees win a few games even though they were badly outplayed.

Even with all their talent, the Yankees have clear places where they need to get better, and losing Judge to free agency would just add to the list of things they need to do this offseason. The Yankees need to do something about shortstop most of all. They didn’t sign any of the big-name free agents from the last offseason. Instead, they chose Isiah Kiner-Falefa, a light hitter who has great range but has trouble finishing plays. He makes a lot of mistakes, and in the playoffs, he lost his job.

The Yankees expect Oswald Peraza and Anthony Volpe to take over the position in the future. Volpe had a great year in Double-A and finished the year in Triple-A. Peraza was very good in Triple-A, and he spent September in the Bronx, even though he only started 14 games there. Even though he only played in a few games and hit .306/.404/.429 and played great defense, he was not put on the ALDS roster.

If the Yankees give out a big contract this offseason, it will go to Judge and not to Carlos Correa, Trea Turner, or another top shortstop. Does Peraza get the ball from the Yankees? Do they put Volpe in the big leagues on the first day of the season, as the Astros did with Jeremy Pea? The shortstop position is a clear one that can be improved. So can left field, the back of the rotation, and the bullpen, where Donaldson showed his age in 2022.

A clear problem: the Yankees’ lineup lacks left-handed hitting. Framber Valdez was the sole left-handed pitcher on Houston’s playoff roster, and that pitching staff just ripped through the Yankees. Perhaps this isn’t a major issue during the regular season (the Yankees had the fifth-highest OPS versus right-handers), but it seems to present itself against a pitching staff that churns out power righties after power righties and a bullpen of relievers with nasty sliders. The Yankees were 23rd in the majors in left-handed plate appearances but tied for eighth in home runs with 77.

It’s important to note that the Yankees are losing a lot of money this offseason, and most of it was going to players who didn’t do much for the team in 2022.

The Yankees changed their team last offseason to improve their defense and add more contact hitters to their lineup, and it mostly worked. They did very well on defense, and their strikeout rate of 22.5 percent was almost the same as the league average (22.4 percent). Now, they need to re-sign Judge, find someone to play left field, improve the left side of the infield, and add more pitchers. There’s money to spend and room to make things better.

Do you want to add more to the list? What questions do you have?