Five questions facing the Yankees for next season

SO . . . ABOUT NO. 99?

That is the question, isn’t it? Aaron Judge passed on the $213.5 million extension the Yankees offered before Opening Day and ended up turning in one of the greatest walk-year seasons any player in any sport has ever had. Though the American League-record 62 home runs stood out, Judge hit for average (.311) and got on base with regularity (an MLB-leading .425 on-base percentage). Because of a combination of injuries and lack of performance from others, he also played more games in centerfield than in right, and the Yankees’ defense never suffered. Rival scouts, since Judge’s days in the minors, have raved about what a complete player he is — hitting, fielding, baserunning, etc. — and never was that more evident than in 2022. Whichever team signs Judge for 2023 and beyond — and the safe bet remains that will be the Yankees, though no one should be counting on a hometown discount of any kind — there almost assuredly will be a “3” at the start of whatever megadeal he puts his name to.

WHAT’S THE FUTURE OF BRIAN CASHMAN?

The five-year contract extension Cashman signed at the end of the 2017 season is set to expire. Indications are, and have been all season, that Hal Steinbrenner is likely to bring the general manager back, though with yet another October disappointment, it is fair to speculate that at the executive level, there may be some voices in the owner’s ear saying the organization should consider moving on. Still, Steinbrenner is extremely comfortable with Cashman, who has been the GM since 1998, and the expectation is that he will return.

WILL HAL STEINBRENNER FORCE ANY CHANGES IN HOW THE ORGANIZATION OPERATES, OR AT LEAST ASK SOME OF THOSE DIFFICULT QUESTIONS?

Though Steinbrenner often mentions his desire to have “balance” in his organization, talk to a cross-section of people behind the scenes — everyone from players to staff to front-office members, etc. — and a decidedly unbalanced picture emerges. That’s nothing new. For several years, one of the worst-kept secrets in the sport is the Yankees’ almost universal adherence to the whims of their analytics department, one of the largest in the majors. There is nothing wrong with analytics, and no successful organization operates without using them. But as one analytics executive from a rival team told Newsday after the 2021 Yankees flamed out in the AL wild-card game: “We’re analysts] not all the same. Some of us are better at this expletive] than others.”

WHO WILL BE THE 2023 SHORTSTOP?

Isiah Kiner-Falefa likely isn’t going anywhere, but the personable 27-year-old, popular among his teammates because of his work ethic and comportment in the face of some rough treatment by fans, might be better suited as a backup. When he got his chances at shortstop after his call-up in August, rookie Oswald Peraza flashed some of the skills that scouts from other teams have been praising for years; expect him to be given a shot to win the starting job in spring training. Peraza is sure to be joined in big-league camp by another top position prospect, Anthony Volpe, who had another standout season in the minors and is considered if not major league-ready, then certainly on the cusp. Could Peraza or Volpe be the starting shortstop come Opening Day 2023? They’ll likely get the opportunity to win the job in camp, but Kiner-Falefa provides a veteran safety net.

WHERE ELSE MIGHT THE YANKEES TURN IN THE FREE-AGENT MARKET?

Anthony Rizzo, along with Judge the most important voice in the clubhouse, has a $16 million player option the Yankees hope he will trigger because if he opts for the marketplace, their chances of re-signing him will decrease. First base is not an area of strength in the organization. Jameson Taillon is among the Yankees’ own free agents, and though they have an interest in bringing him back, the righthander, in what is not a strong free-agent pitching market, could land a far bigger deal than the Yankees are comfortable offering. As it stands, the Yankees will enter spring training 2023 with six starters for five spots — Gerrit Cole, Nestor Cortes, Luis Severino, Frankie Montas, Clarke Schmidt and Domingo German. Michael King, among the best relievers in baseball before an elbow injury in July ended his season, likely will be in that mix, too. King and the Yankees still see him as a starter.