2. Carl Pavano
There were times where one had to wonder if Carl Pavano collected his paycheck from the New York Yankees wearing a ski mask and holding a gun.
Pavano had been a solid middle of the rotation arm prior to signing with the Yankees. He had made over 30 starts for three consecutive years and had made his first All Star Game in 2004. As he was 28 years old, it seemed as though the Yankees were getting a solid pitcher for the rest of his hypothetical prime.
It is important to note that Pavano had made at least 30 starts in each of the three years prior to signing with the Yankees. That is because he made a grand total of 26 starts in his four years in pinstripes, with 17 of those coming in 2005. His numerous injuries, including a strained butt that caused him to miss the entire 2006 season (seriously) and a car accident he only told the organization about on the day he was scheduled to pitch, ruined his tenure.
In exchange for that four year, $39.95 million contract, Pavano posted a 9-8 record with a 5.00 ERA and a 1.455 WHiP. He struck out 75 batters with 30 walks in his 145.2 innings as he made over $1.5 million per start. Naturally, once he left the Yankees, he found his form once again until injuries forced him to retire.
The New York Yankees thought they were getting a key piece for their rotation in Carl Pavano. Instead, they landed someone who just could not get on the mound.