These top list of Yankees' biggest Winter Meetings moves

A bleary-eyed Brian Cashman sat in a windowless conference room deep within a San Diego luxury hotel, confessing he had not slept the night before. It was the 2022 Winter Meetings, and even the most seasoned Yankees officials feared that Aaron Judge might be about to hand in his pinstripes.

Instead, those negotiations pivoted with an international phone call. Judge was in a hallway of his boyhood home in Northern California, speaking directly to managing general partner Hal Steinbrenner, his rental car parked on a roadside somewhere in Italy.

All background noise melted when Steinbrenner asked directly: “Do you want to be a Yankee?” Within minutes, they agreed verbally on a nine-year, $360 million contract, one that carried the added honor and responsibility of serving as the franchise’s first captain since Derek Jeter.

Each Winter Meetings has been different over the years, and though Cashman usually portrays pessimism about his chances of completing a deal, the veteran general manager has rarely departed empty-handed. Here’s a look at five more significant Yankees Winter Meetings transactions:

1) Gerrit Cole (2019)
Word traveled rapidly throughout the crowded hallways of a San Diego luxury hotel on a Wednesday evening, an excited murmur growing into full-throated bellows by the bar. The Yankees had succeeded in their mission, wooing Cole with what was then the richest contract issued to a free-agent pitcher -- nine years and $324 million.

It was a full-circle moment for Cole, previously an ace with the Pirates and Astros. More than a decade before throwing his first big league pitch, he’d arched his 11-year-old frame over the right-field wall prior to a 2001 World Series game, attempting to secure the attention of stars like Jeter and Paul O'Neill by hoisting a hand-written placard that read: "Yankee Fan Today, Tomorrow, Forever."

2) Juan Soto (2023)
For months, the Yankees had envisioned Soto in pinstripes, taking aim at Yankee Stadium’s right-field porch. Though it proved to only be a one-year rental, the Bombers swung big to complete a blockbuster seven-player deal that was the talk of the Winter Meetings at the Gaylord Opryland Resort & Convention Center.

Soto came with outfielder Trent Grisham in exchange for five players: right-handers Michael King, Drew Thorpe, Jhony Brito and Randy Vásquez, plus catcher Kyle Higashioka. Soto hit 41 homers and batted .288 in his lone season with the Yanks, helping lead them to their first World Series since 2009. When Soto jumped to the Mets late in 2024, the Yanks pivoted to sign left-hander Max Fried, producing another significant Winter Meetings headline.

3) CC Sabathia (2008)
The new Yankee Stadium was nearing completion, and the Yankees needed an ace. Cashman and Sabathia met twice in Las Vegas, making some progress but unable to tune out distractions. With the rest of the baseball world preoccupied with slot machines and table games, Cashman slipped out of the Bellagio hotel and boarded a commercial jet to the San Francisco Bay Area, in hot pursuit of the game’s most prized free-agent pitcher.

Passing through Sabathia’s Vallejo, Calif., doorway, entering a sunken living room that he recognized from MTV Cribs, Cashman resolved to perform what he called his “best John Calipari impression.” There, the GM and Sabathia hashed out the terms of a deal that would help produce the franchise’s 27th World Series title, agreeing to a seven-year, $161 million contract. Sabathia went 97-56 with a 3.73 ERA (114 ERA+) over the life of that original contract, then remained in New York for another four years.

4) Giancarlo Stanton (2017)
The Marlins arrived at the Winter Meetings intending to rebuild, gauging trade interest in the reigning National League MVP. The Yankees already had one hulking slugging outfielder in Judge, and the prospect of having Stanton in the same lineup -- fresh off a campaign in which he paced the Majors with 59 home runs -- was too delicious to pass up.

Stanton’s blockbuster deal shook up the 2017 Winter Meetings at the Walt Disney World Swan & Dolphin Resort, the outfielder beaming as he held his pinstriped No. 27 jersey in front of the news cameras. New York shipped infielder Starlin Castro, right-hander Jorge Guzmán and infielder José Devers to Miami in exchange for Stanton and cash considerations. Stanton led the Yanks with 38 homers and 100 RBIs in his first season with the team.

5) Rickey Henderson (1984)
Already a four-time All-Star and the game’s premier leadoff hitter, Henderson’s availability highlighted the 1984 Winter Meetings at the Hyatt Regency in Houston. With the Athletics believing that they would be unable to retain Henderson long term, then-Yankees general manager Clyde King pounced, fitting the future Hall of Famer for pinstripes as part of a six-player deal.

New York acquired Henderson, right-hander Bert Bradley and cash considerations in the deal. Oakland picked up the Yankees’ No. 2 reliever in Jay Howell, plus four Minor Leaguers who went on to big league careers -- Tim Birtsas, Eric Plunk, Stan Javier and Jose Rijo. Henderson was an All-Star in each of his four full seasons as a Yankee, and his 326 stolen bases were a franchise record until 2011.