Ranking the Worst Trade Deadline Deals in Yankees History

The New York Yankees are the top dogs in the AL this year. They've played to the tune of a 64-35 record and have built a substantial lead in the AL East. That being said, they're still looking to improve at the trade deadline. Rumors have swirled all year that they're in the market for a starter.

But if they're wise, they'll learn from the mistakes of the past. With the MLB trade deadline approaching, let's take a look back at the worst deadline deals in Yankees history.

3. OF Dustin Fowler, INF Jorge Mateo and SP James Kaprelian for SP Sonny Gray

Tampa Bay Rays v New York Yankees / Elsa/Getty Images

It's not so much what the Yankees lost in this deal but what they got in return that makes it so abysmal. While Fowler, Mateo and Kaprelian have all yet to pan out for the Oakland Athletics, Sonny Gray's tenure with New York was an unprecedented disaster. Gray posted a 4.51 ERA in 41 appearances for the Yankees. His 2018 season was particularly abysmal. In 59.1 innings at Yankee Stadium last year, Gray put up a 6.98 ERA and allowed a .932 opponent OPS. Everything about his time in pinstripes was a trainwreck, and the Yankees should be thankful that they didn't ship out more than what they did to get him.

2. RP Mark Melancon and UTL Jimmy Paredes for 1B Lance Berkman

San Francisco Giants v Colorado Rockies / Matthew Stockman/Getty Images

Fresh off of their 27th World Series victory, the 2010 edition of the Yankees were eager to repeat as champs. To bolster the lineup, Brian Cashman traded young reliever Mark Melancon and prospect Jimmy Paredes to the Astros in exchange for slugging first baseman Lance Berkman. The move didn't pan out. The 34-year-old Berkman posted a dismal .707 OPS in just half of a season with New York and hit just one home run. Melancon, meanwhile, blossomed into a star reliever and is still pitching today. Since the start of 2011, he's posted a 2.75 ERA and has logged 183 saves. It's safe to say the Yankees drew the short end of the stick on this one.

1. OF Jay Buhner for 1B Ken Phelps

Preparations Are Made At The London Stadium Ahead Of Yankees V Red Sox Baseball Weekend / Peter Summers/Getty Images

The swap of Buhner and Phelps remains one of the most lopsided deadline deals in New York Yankees history. Phelps came to New York and played 131 games, putting up a mediocre .781 OPS with the team. As for Buhner, he made the most of his time with his new team in the Seattle Mariners. The 1988 deadline acquisition went on to hit 307 home runs in Seattle, even receiving MVP votes in three consecutive years from 1995 to 1997.