What's in store for Yanks at Winter Meetings?

If Brian Cashman owned a magic wand, the Yankees’ general manager has said, the club would have held a news conference to celebrate a long-term extension for Aaron Judge at Yankee Stadium weeks ago. The Winter Meetings in San Diego would be an acceptable second choice for that announcement.

Three years after rattling the baseball landscape by agreeing to a massive deal with ace Gerrit Cole, the Yankees will return to the hallways of the Manchester Grand Hyatt this coming week, hoping to learn that Judge will accept their invitation to continue playing in the Bronx for the better part of the next decade.

“He’s our best player,” Cashman said. “He plays amazing defense. He’s an amazing offensive player and baserunner. He can beat you on all ends. He’s a great team leader, someone that’s an impactful player in that clubhouse. Our fans love him, too. There’s not one box he hasn’t checked. Obviously, that’s why he’s in a great position as a free agent.”

Recently crowned as the American League’s Most Valuable Player coming off a fantastic contractual walk year in which he hit 62 home runs, eclipsing Roger Maris’ 61-year-old single-season AL record, Judge turned down a seven-year, $213.5 million extension in March.

The Yankees have extended a new offer to Judge, believed to be north of $300 million; the Dodgers and Giants are also interested in the slugger.

“We will be in play with trying to improve our team in other aspects, not just our attempt to sign Judge,” Cashman said. “We have more work to do. He’s quite aware of that. Obviously, he wants to [play for] a team that’s capable of taking a shot at a World Series title. There are certain aspects that we need to attend to, and it would be perfect if we can deal with all of that this winter.”

Key Events

• Monday, Dec. 5: All-MLB Team announced
• Tuesday, Dec. 6: Inaugural Draft Lottery, AL/NL Relievers of Year announced
• Wednesday, Dec. 7: Rule 5 Draft

Club Needs

Judge has left an MVP-sized hole in right field, but the Yankees also need a left fielder, with Andrew Benintendi having reached free agency. The Yanks are monitoring the starting pitching market as well, with published reports connecting them to Carlos Rodón and Japanese free agent Kodai Senga. Cashman has said that he is comfortable with Clay Holmes as the closer.

Potential Trade Candidates

Gleyber Torres could be on the move this winter. The Yankees discussed trading Torres to the Marlins ahead of the Aug. 2 Trade Deadline in a potential deal for right-hander Pablo López, and the clubs could re-engage during the Winter Meetings. Aaron Hicks is expected to be on the trading block this offseason; he has three years remaining under contract. The Yanks would discuss third baseman Josh Donaldson and shortstop Isiah Kiner-Falefa with interested clubs.

Prospects to Know

Managing general partner Hal Steinbrenner has said that he intends for shortstops Oswald Peraza and Anthony Volpe to receive legitimate opportunities to win big league jobs in the spring, envisioning them as the future of the Bombers’ infield. Volpe and Peraza are the Yankees’ Nos. 1 and 3 prospects, respectively, according to MLB Pipeline.

Rule 5 Draft

Catcher Josh Breaux, the Yanks’ No. 20 prospect, is among the unprotected players who could draw interest in the Rule 5 Draft. Breaux has power, slugging 19 homers in 94 games this past season, and has been compared to Gary Sánchez. Others include catcher Anthony Siegler, pitchers Zach Green and Matt Sauer, and infielders Jesús Bastidas and Andres Chaparro. The Yanks have one open space on their 40-man roster.

Burning Question

Will Judge sign the deal? That is the domino that needs to fall to determine the rest of the offseason. Steinbrenner has said that the Yankees have enough cash to ink Judge, whose contract’s average annual value may exceed the $35.5 million Mike Trout earns from the Angels, and still do more this winter. That suggests that if Judge signs elsewhere, the Yanks may respond with an offseason spending spree like the one they had in the winter of 2008-09, bringing in free agents CC Sabathia, A.J. Burnett and Mark Teixeira to help open the new ballpark.