15 worst trades in New York Yankees history

New York Yankees v Toronto Blue Jays
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4. July 31, 2004: Yankees Acquire Esteban Loaiza for Jose Contreras, Cash, Dignity

Long before Loaiza was headed to prison for trafficking cocaine, he was wrecking the 2004 Yankees season from the inside out.

Imagine if those Yankees had simply kept Andy Pettitte instead of trying to "level up" with Brown and Vazquez, then trying to stem the tide with Loaiza at the deadline? I've certainly stayed up all night thinking about this before!

Loaiza broke out with the 2003 White Sox, finishing second in the Cy Young race with a 21-9 record, 2.90 ERA, and a league-leading 207 Ks in 226.1 innings pitched. He was no longer that guy in 2004, but somehow received a courtesy All-Star invite for going 9-5 with a 4.86 ERA at the break.

After the Yankees obtained him in exchange for their own scuffling project in Contreras, he ... oh boy, brace yourselves ... went 1-2 with an 8.50 ERA in 10 games (six starts). Know what you're about to ask: Did he somehow end up being used in the ALCS against the Red Sox anyway? He sure did! He was surprisingly competent, posting a 1.42 ERA in 6.1 innings across two games.

Unfortunately, the single earned run he allowed was a walk-off hit by David Ortiz as the curse drums began to beat louder. Oops! Where's Pettitte when you desperately need him?