Yankees: The worst trades in franchise history

6. November 26, 1986. New York trades Doug Drabek, Logan Easley, and Brian Fisher to the Pittsburgh Pirates for Pat Clements, Cecilio Guante, and Rick Rhoden.

There was a common thread among many of the Yankees trades in the 1980s. The franchise wasn’t having difficulties on the offensive side of things, but they were constantly looking to add starting pitching (a theme that has resurfaced in other decades since). More often than not those trades failed to work out. Former Yanks Go Yard writer Billy Brost summed it up pretty well a few years ago, “some of the generation’s best players were practically given away for stop-gap measures, and quick fixes that rarely, if ever, worked to the Yankees advantage.”

Doug Drabek was one of those players. The right-hander had a serviceable rookie season for the Yankees in 1986, going 7-8 with a 4.10 ERA. Following the season, however, it seemed the Yankees were dead-set on moving him and there were multiple teams in pursuit (a separate trade weeks later with the White Sox was made which Murray Chass described in the New York Times as a “substitute for the deal in which the Yankees were supposed to give the White Sox Drabek”).

Drabek flourished with the Pirates. He won 15 games in 1988. He took home the NL Cy Young Award in 1990, going 22-6 with a 2.76 ERA. He was a key piece in the Pirates run of division titles in the early 90s.

Easley had two stints in the Pirates bullpen. Fisher spent two years in their rotation.

Clements spent two disappointing seasons in the Yankees bullpen. Guante’s tenure wasn’t much better, but at least put up strong enough numbers over the first half of the 1988 season that the Yankees could trade him to Texas.

Rick Rhoden was useful for New York in the two seasons he spent there. He won 16 games his first season with the team and 12 more the year after. After the 1989 season, he was done with baseball.

5. December 6, 2003. New York trades Nick Johnson, Randy Choate, and Juan Rivera to the Montreal Expos for Javier Vazquez.

Having watched the rival Red Sox add Curt Schilling just days earlier, the Yankees felt the need to respond with a pitching addition of their own. It wouldn’t be the first or last time one of these two teams made a move in response to the other.

Vazquez was coming off a string of successful seasons in Montreal in which he averaged over 200 innings pitched. While not a flashy addition like Schilling, he seemed like a quality pickup. While the results in New York weren’t quite the same as what some expected, Vazquez was at least somewhat useful in his first season in the Bronx.

He’d go 14-10 on the year, posting a 4.91 ERA. Vazquez made the All-Star team with a strong first half, but at season’s end the Yankees would move on from him — using him as part of the package to bring in Randy Johnson from Arizona.

Nick Johnson had just hit .284/.422/.472 the prior season. The contact-hitting first baseman had become a fan favorite in New York. He’d continue to get on base consistently for the Expos and Nationals before injuries shortened his career.

Rivera flashed some power, hitting 132 home runs over his 12-year career. Choate, meanwhile, spent another eleven years in the majors after the trade.