Yankees: The worst trades in franchise history

8. December 22, 2009. New York trades Melky Cabrera, Mike Dunn, Arodys Vizcaino, and cash considerations to the Atlanta Braves for Javier Vazquez and Boone Logan.

The Yankees were eager to add to their roster with the goal of winning again in 2009. Pitching wasn’t really an area the team needed to address, but once again they found themselves eager to add an arm when the opportunity presented itself. The Braves were suddenly flush with starting pitching after signing Tim Hudson as a free agent. The two teams were easy trade partners.

Javier Vazquez had just finished a career-best year. He won 15 games, posted a 2.87 ERA, and was second the NL in strikeouts. He’d finish fourth in Cy Young voting. On paper, he looked like a nice addition to the Yankees rotation.

Vazquez failed to produce in New York, however. He went 10-10 with an ERA that ballooned to 5.32. Nearly every peripheral statistic took a step back from the season prior. The Yankees let him walk via free agency after the season.

You would think the Yankees had learned their lesson when it comes to Vazquez, but this was actually the second time he was acquired by New York (more on the other trade later).

Logan proved useful for the Yankees, serving as a left-handed option in the bullpen for four seasons, posting a 3.38 ERA in 256 appearances.

Cabrera was the key piece New York gave up, but he’d become somewhat expendable with Brett Gardner’s emergence. Dunn and Vizcaino played pivotal roles for the Braves bullpen over the coming seasons.

7. July 31, 2004. New York trades Jose Contreras and cash considerations to the Chicago White Sox for Esteban Loaiza.

In 2003, Esteban Loaiza won 21 games with a 2.90 ERA en route to finishing second in the AL Cy Young voting. The following summer he’d won nine games already by late July, albeit with peripheral numbers (namely his ERA, WHIP, and K/9) that had been far worse than what he’d done the season before. The Yankees sat 8.5 games ahead in the AL East at the trade deadline but still insisted on adding another starting pitcher.

Loaiza made just six starts for New York before landing in the bullpen, posting an 8.50 ERA and 2.055 WHIP over 42.1 innings of work. Letting him leave via free agency after the season was an easy decision.

Jose Contreras, meanwhile, became a reliable piece of the White Sox rotation. He’d win 15 games in 2005 and helped the club win the World Series. The following year brought about his lone All-Star appearance. Overall he’d throw 900 innings for Chicago over six seasons with a 4.66 ERA. The Yankees gave up on him just a year and a half after signing him out of Cuba.