Best Trade Deadline Acquisitions in New York Yankees History

The 2022 MLB trade deadline has come and gone, and with the dust settled, fans will engage in their own analytic or not-so-analytic assessment of this year’s activity. As history shows, transactions at the deadline can be the catalyst that drives an immediate postseason run or sets a foundation for franchise excellence for years to come.

The New York Yankees, in their storied history, have not been shy at the trade deadline, filling gaps where needed, often with a view toward short-term return on investment.

Sifting through the multitude of Yankee deadline deals past and present, the challenge becomes to find those jewels that rightfully belong on the short list of the best in Yankee history. Firing up the hot stove, here are my top three:

1) David Cone

The 1994 Cy Young Award winner, the Yankees, acquired David Cone from the Toronto Blue Jays at the 1995 trade deadline. In return, New York sent a trio of players – pitchers Marty Janzen, Mike Gordon, and Jason Jarvis to the Jays. Cone made an immediate impact in Yankee pinstripes, going 9-2 with a 3.82 ERA over 13 starts. In the ALDS against the Seattle Mariners, Cone worked 7.2 innings in the decisive Game 5, earning a no-decision in the Mariners’ series-clinching 6-5 victory.

In 1996, Cone underwent mid-season surgery to repair an aneurysm in his right shoulder. His career in jeopardy, Cone returned from two months of rehabilitation with a stunning and inspirational start against the Oakland A’s, throwing seven no-hit innings in a 5-0 Yankees victory. In the World Series that year, down two games to none to the Atlanta Braves, Cone is credited with turning the Series around, winning game three, and giving up just one run over six innings. Buoyed by Cone’s victory, the Yankees went on to win the Series 4-2.

Cone made the All-Star team in both 1997 and 1999 and won four World Series rings while a member of the Yankees. He won 20 games in 1998 and, from 1997-2000, averaged 187.6 innings pitched.

In his 1999 season, Cone went 12-9 with a 3.44 ERA, including pitching a perfect game on July 18 against the Montreal Expos.

Of the players Toronto received for Cone, Gordon and Jarvis never pitched in the Majors. Janzen made 27 appearances, 11 of them starts, with a record of 6-7 and 6.39 ERA over 98.2 innings.

2) David Justice

At the 2000 trade deadline, Yankees GM Brian Cashman, in search of a left-handed power bat, acquired outfielder David Justice from the Cleveland Indians in return for outfielder Ricky Ledee and pitchers Jake Westbrook and Zach Day. At the time of the deal, Justice was hitting .265 with 21 home runs and 58 RBI in 68 games with the Tribe. He thrived with the Bronx Bombers, hitting .305 with 20 round trippers and 60 RBI. The Yankees caught fire after the deadline, capturing the American League East division.

In the ALCS against the Seattle Mariners, Justice launched a go-ahead three-run homer in the seventh inning, a lead the Yankees would not relinquish, capturing the Series in six games. The blast earned Justice MVP honors, and the Yankees would go on to win the 2000 World Series, downing the New York Mets four games to one.

Though Justice played just one more season with the Yanks, there is no denying the impact he had on New York’s 2000 drive to the World Series. A deserving second in the top Yankee deadline maneuvers.

3) Cecil Fielder

The trade deadline is never over until it’s over, as proven in 1996 when the Yankees acquired slugger Cecil Fielder from the Detroit Tigers with the midnight deadline rapidly approaching. New York shipped veteran outfielder Ruben Sierra and minor league pitcher Matt Drews to Detriot. In 53 games with the Yankees, Fielder hit .260 and launched 13 home runs with 37 RBI. He made his most significant impact in the postseason that year, hitting .308 with three long balls and 14 RBI, helping the Yankees win the World Series as they downed the defending champion Atlanta Braves in six games. Sierra played in the 1996 season with the Tigers and went on to suit up for seven more teams, including the Yankees, from 2003 to 2005.