5 of Yanks' biggest Winter Meetings moves

December 7th, 2020

Word traveled rapidly throughout the crowded hallways of a San Diego luxury hotel on a Wednesday evening one year ago, an excited murmur growing into full-throated bellows by the bar. The Yankees had succeeded in their Winter Meetings mission, wooing Gerrit Cole with the richest contract ever issued to a free-agent pitcher.

Cole’s arrival presented a new chapter in the Yankees’ history of creating noise at the Winter Meetings, a week-long extravaganza for the game’s movers and shakers. Each trip has been different, and though general manager Brian Cashman usually arrives pessimistic about his chances of completing a deal, he has rarely departed empty-handed.

The 2020 meetings will be virtual, removing the visual of a sequestered Cashman tossing a Nerf football around a hotel suite. Since text messages have fueled many of the team’s recent negotiations, team brass should still be able to operate. Here is a look at five more of the Yankees’ most significant Winter Meetings transactions:

1) CC Sabathia (2008)
The new Yankee Stadium was nearing completion, and the Yankees needed an ace to stabilize their rotation. 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 had previously seen on MTV Cribs, Cashman resolved to perform what he called his “best John Calipari impression,” intending to land the recruit. 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.

2) Willie Randolph (1975)
With writers growing restless at the 1975 Winter Meetings in Hollywood, Fla., Yankees president Gabe Paul stepped to the plate with a pair of blockbuster moves, shipping outfielder Bobby Bonds to the Angels and right-hander Doc Medich to the Pirates. In return, the Yankees received five players, several of whom would play key roles in helping the franchise reach the next three World Series.

Pittsburgh packaged Randolph -- then lauded one of the game’s top Minor League second basemen -- with pitchers Ken Brett and Dock Ellis. California sent pitcher Ed Figueroa and outfielder Mickey Rivers to New York. The Brooklyn-born Randolph became a mainstay in the Yankees' infield for 13 seasons, making five All-Star teams and winning an American League Silver Slugger Award in 1980.

3) Giancarlo Stanton (2015)
The Marlins arrived at the Winter Meetings intending to rebuild, gauging trade interest in the reigning National League MVP Award winner. The Yankees already had one hulking, slugging outfielder in Aaron 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 2015 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 Guzman and infielder Jose 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, but injuries have limited him to 41 regular-season games over the past two years.

4) 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.

5) Curtis Granderson (2009)
The 2009 Winter Meetings were one of the coldest in recent memory, with temperatures in the single digits that week in snowy Indianapolis. The defending World Series champions added sizzle to the Hot Stove by participating with the Tigers and D-backs in a three-team trade, installing Granderson into the outfield as the Yankees prepared to move on from the Johnny Damon and Hideki Matsui eras.

Left-hander Phil Coke, outfielder Austin Jackson and right-hander Ian Kennedy departed New York in the old-school swap, big names filling needs across the board. Coke, Jackson, Max Scherzer and Daniel Schlereth went to Detroit, while Kennedy and Edwin Jackson went to Arizona. Granderson made two All-Star teams and won an AL Silver Slugger Award during his four years in pinstripes.