NEW YORK -- The final on-field action of the Yankees’ 2022 season occurred at 12:08 a.m. ET on Monday, as Aaron Judge tapped a Ryan Pressly slider back to the pitcher. The Astros’ celebration of an American League Championship Series sweep began even before the ball reached first base.

Judge ran the play out, then watched for a few seconds as he trudged toward the dugout steps, descending into the uncertainty of a winter that may determine the franchise’s direction for years to come. The Yankees won 99 regular-season contests in this historic season of No. 99, claiming the American League East by seven games, but Judge himself declared it all “a failure.”

It has been more than 4,700 days since the Yankees were the last team standing. Despite five trips to the ALCS and more than a billion dollars spent in player salaries over that span, the ultimate prize of a 28th World Series title has eluded the winningest franchise in the sport’s history.

“So much goes into it, trying to climb to the top of the mountain,” manager Aaron Boone said. “Unfortunately, we haven’t been able to get there yet. I know it will continue to motivate everyone in there to try and get there.”

Here are five important questions that the Yankees must answer as they regroup for 2023.

1. Will Aaron Judge return, and how much would it cost?
When Judge turned down a seven-year, $213.5 million extension from the Yankees before Opening Day, it all but assured that the outfielder would enter free agency after the season. In what general manager Brian Cashman referred to as “the all-time best bet,” Judge turned in an offensive season for the ages, shattering Roger Maris’ 61-year-old single-season American League home run record while pacing the circuit in numerous categories.

The proposed $30.5 million average annual salary (which, as Cashman pointed out at the time, would have been the largest ever issued to a Yankees position player) now looks quaint. Most insiders suggest that Judge’s bounty will set a new league-high watermark, exceeding not only Mike Trout’s AAV of $35.54 million but possibly Max Scherzer’s $43.3 million AAV, and likely spanning at least seven or eight years.

Judge said that he was “disappointed” by the club’s April offer and was upset by Cashman’s public remarks outlining the contract structure. Though he said he would prefer to stay with the franchise that drafted and developed him, Judge has also noted that he is looking forward to experiencing the free agency process and entertaining all 30 clubs. Don’t count on a hometown discount; the Yankees will have to present the best offer. It’s difficult to imagine Judge in another uniform, but the same could’ve been said a winter ago about Freddie Freeman.

Asked if he still wanted to be a Yankee, Judge said: “I’ve been clear about that since I first wore the pinstripes, but we couldn’t get something done before Spring Training. Now I’m a free agent. We’ll see what happens.”

2. Will Brian Cashman and Aaron Boone be back?
Cashman’s five-year contract will expire after the World Series. While the expectation is that managing general partner Hal Steinbrenner will offer the longtime general manager a contract to return to a post he has held since 1998, there must be a serious conversation about why this championship window is closing without a return to the World Series.

It was primarily Cashman’s decision to part ways with Joe Girardi after a Game 7 loss to the Astros in the 2017 ALCS, voicing a belief that Boone’s communication style would help push a young core to its potential. Steinbrenner said at the time that, even if the Yankees had won the World Series, Girardi would have been let go. But Boone has never made it farther than Girardi; the closest was a heartbreaking ALCS Game 6 loss to the same Houston club in ’19. Steinbrenner must know why the gap between the Yankees and Astros has widened.

Boone received a three-year extension after the Yankees lost the 2021 AL Wild Card Game at Fenway Park, so his job is likely secure. But his managerial moves, particularly his concerning bullpen use in the postseason, deserve scrutiny. There must be flexibility to deviate from a preordained script and make real-time decisions. The Yankees must also consider the fate of Boone’s coaching staff, especially pitching coach Matt Blake, whose contract is up.

3. Who is next year’s shortstop?
The Yankees spent weeks citing internal metrics and insisting that Isiah Kiner-Falefa was one of the top defensive shortstops in the AL. That confidence seemed shaken after falling into a 2-1 hole in the best-of-five AL Division Series against the Guardians. Oswaldo Cabrera and Oswald Peraza worked into the mix, though Kiner-Falefa also started two games in the ALCS.

Acquired from the Twins as part of the Josh Donaldson deal, Kiner-Falefa was viewed as a sure-handed stopgap while the Yankees allowed Peraza and top prospect Anthony Volpe to prepare down on the farm. They hoped playing home games in Yankee Stadium would bolster his offensive numbers, but his .261/.314/.327 slash line (84 OPS+) was in line with his career norms.

Kiner-Falefa said that he hopes to return, but acknowledged, “They could trade me.” Assuming the Yankees don’t delve into a shortstop free agent market headlined by Trea Turner, Peraza and Volpe could come into the spring with realistic chances of cracking the Opening Day roster.

4. Will the Yankees pursue Anthony Rizzo and Andrew Benintendi?
In the wake of the ALCS loss, Rizzo said that he has not yet decided on his player option for next season; Rizzo can turn down the $16 million owed to him and become a free agent. The Yankees love Rizzo’s left-handed power bat, above-average defense at first base and clubhouse presence, though his recurring back issues are a concern. Without Rizzo, DJ LeMahieu would be in line as the starting first baseman (LeMahieu, by the way, is hoping to avoid surgery to repair a fracture in his right big toe and ligament damage in his second toe).

Benintendi also is part of a free agent group that includes Aroldis Chapman, Zack Britton, Jameson Taillon, Chad Green, Miguel Castro and Matt Carpenter. A Gold Glover who hit .254/.331/.404 (109 OPS+) as a Yankee, Benintendi said he would be open to a return. Currently, the only Yankees outfielders under contract are Harrison Bader, Cabrera and Aaron Hicks. The club will explore moving Hicks, who still has three years under contract.

5. How much will the pitching staff change?
For the most part, the Yanks’ postseason exit was on the bats, not the arms. The good news is that the Yankees have control of their top four starters, with Gerrit Cole and Nestor Cortes under contract and Luis Severino’s $15 million option expected to be picked up. Frankie Montas didn’t provide much after his midseason acquisition from the Athletics, but the Yankees will hope an entire offseason of rest can cure the shoulder issues that hindered him. Clarke Schmidt could get a look as the No. 5 starter, though Taillon said that he’d be open to returning.

Strong bullpens have been a hallmark of Cashman’s teams. That wasn’t the case in ’22, when an injury-decimated staff went into the postseason with no set closer and no lead feeling safe. Clay Holmes, Jonathan Loáisiga, Wandy Peralta, Lou Trivino and Ron Marinaccio all seem to be parts of the puzzle, and Michael King should return in the spring. Still, look for the Yankees to attempt to upgrade the group via trade or free agency.