7. Jaret Wright: Three Years, $21 Million, 2004
Even though he only finishes seventh here, Jaret Wright deserves a special designation. There was no discernible reason for his meltdown in pinstripes, though it certainly happened anyway. He was an ex-Yankee killer, which made the regression all the more painful. He made sense at the time, though his tenure ended up arguably worse than the other high-dollar free agent pitcher New York imported that offseason.
All in all, the surly Wright was a massive bummer, and yet another in a long line of arms the Yankees paid based on personal history and one good year.
As a hard-throwing rookie with Cleveland, Wright displayed poise on the mound in the Bronx, defeating Andy Pettitte at Yankee Stadium in Game 2 of the 1997 ALDS with six solid innings. He also beat Pettitte at home in Game 5, bringing a bit of mystique and Bomber nerves to the 1998 ALCS, where New York found their record-setting team on the brink.
That year, Wright collapsed under the pressure, allowing six earned runs in 6.2 innings. Vastly preferable.
Coming off a 2004 season that ended in disaster, the Yankees looked to reload significantly, and set their sights on Wright, who'd just gone 15-8 in 186.1 innings (3.28 ERA) for the Atlanta Braves at the age of 28.
Unfortunately, once he got to the Bronx, he looked a lot more like the version of himself who'd posted a 15.71 ERA in eight games for Cleveland back in 2002. 6.08 ERA in 63.2 innings his first year in New York. 4.49 ERA in 140.1 innings his next season, with a shoulder barking. In Baltimore for the third year of his Yankees contract. Like clockwork.