27. Carl Pavano, 2005: Four Years, $39.95 Million
Wow, ranking the best contract in Yankees history 27th all time?! Where do these guys get off?!
Pavano was an unmitigated disaster in pinstripes -- and, it should be noted, grew up a Red Sox fan in New Britain, CT and started his career in the Red Sox organization.
The Yankees, after being embarrassed in 2004, paid for past performance (and outbid Boston) to secure Pavano's services coming off an 18-8, 3.00 ERA season where he put it all together in Florida. He only made 26 starts across four seasons with the Yankees, going 4-6 with a 4.77 ERA in 17 starts in his "fullest" season in '05.
Among Pavano's prime transgressions were sustaining a bruised buttocks in spring training and lying about a car accident, withholding from the Yankees the important information that he'd busted some ribs.
In other words, someone you definitely want cracking your Top 30 deals.