New York Yankees History: The best Yankee acquisitions during the Winter Meetings (video)

New York Yankees, Yankees, CC Sabathia
Apr 29, 2018; Anaheim, CA, USA; New York Yankees starting pitcher CC Sabathia (52) reacts while leaving the field during the seventh inning against the Los Angeles Angels at Angel Stadium of Anaheim. Mandatory Credit: Kelvin Kuo-USA TODAY Sports

The New York Yankees, in their illustrious 107-year history, have made quite a few big-time purchases and trades. The biggest was the worst for the Boston Red Sox when their owner being money short for his other endeavors sold Babe Ruth to the New York Yankees, and we all know how that turned out. But in recent years, the Yankees have made some pretty impressive deals in the Winter Meetings. The first one was technically not during the meetings but a few days before at Dallas, Texas.

Mike Mussina (2000):

Just a few days before the Winter Meetings, The New York Yankees signed the Baltimore Orioles Mike Mussina. It turned out to be one of the best acquisitions of recent times. Mussina ended up spending eight highly successful years with the Yankees at the top of their pitching rotation. He had a 123-72 record with a 3.82 ERA.

From 1992 to 2008, Mussina never had a losing season. In fact, he is one of the only pitchers to ever have 17 consectutive seasons of winning 11 or more games a year. Mussina was a smart pitcher who pitched with amazing intensity. He also saved his greatest achievement for the very last game of his career. In his very last year, he became the oldest pitcher in baseball to achieve 20 wins in his last season.

I could insert a video here of his many strikeouts, but I would rather show you a video of his intensive pitching style. On May 31, 2006, Mussina held the Tigers in check for most of the night at Comerica Park, taking a shutout attempt into the ninth. After allowing a run, manager Joe Torre made motions toward emerging from the dugout to remove Mussina from the game. But “Moose” was not having it: Bellowing “No, stay there!” at your manager in the heat of the moment is a power move, for sure.
Mussina then buckled down, striking out Carlos Guillen to nail down the complete-game win on just 101 pitches.

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 over the life of that original contract, then remained in New York for another four years.

Willie Randolph (1975)

In December of 1975, the Winter Meeting was held in Hollywood, Florida. The 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. These three players would play key roles in helping the franchise reach the next three World Series.

The biggest pick up was Willie Randolph from the Pittsburgh Pirates. Randolph was surely one of the best second basemen in the baseball Minor Leagues at the time. They also picked up 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. Ed Figueroa and speedy Mickey Rivers would also be big contributors to the New York Yankees.

Rickey Henderson (1984)

The 1984 Winter meetings were held at the Hyatt Regency in Houston, Texas. The New York Yankees, general manager Clyde King did no less than obtaining the services of Ricky Henderson, a four-time All-Star and the games’ number one leadoff hitter. The Oakland Athletics, just a few years away from being the Kansas City Athletics, felt that they would not be able to hold on to  Henderson long term, so the delt him the New York Yankees. The future Hall of Fame player was a Yankee.

The Yankees sent Jay Howell, plus four Minor Leaguers, and cash to get the Henderson deal done. Ricky 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. Henderson ended with the Yankees getting 78 home runs while batting .288 and with an OPS of .1048.

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.

Giancarlo Stanton (2017)

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 Aaron Judge, a hulking slugger in right field, and the prospect of obtaining Stanton the 2017 National League MVP with 59 home runs was more than the Yankees could possibly resist.  The New York Yankees sent Starlin Castro, pitcher Jorge Guzman and Jose Dever to the Miami Marlins along with cash to make the deal happen, and Giancarlo Stanton was a New York Yankee.

Stanton’s blockbuster deal shook up the 2015 Winter Meetings at the Walt Disney World Swan & Dolphin Resort. Later the Yankees announced officially at Yankee Stadium that they acquired Stanton standing next to owner Hal Steinbrenner. It was the joyest occasion. In 2018 Stanton would hit 38 homers for the Yankees with 100 RBIs. But that would signal the end of the Joy. Stanton has had only 41 homers in the last two years and has been off the field with constant injuries as much as on the field. Only history will tell if this is one of the worst trades the Yankees have made, right next to Jacoby Ellsbury.

What moves the New York Yankees will make during these virtual Winter Meeting has yet to be seen.’s Columnist William Parlee is a member of the Society for American Baseball Research. Follow me on Twitter @parleewilliam.