3. Alex Rodriguez: 10 Years, $275 Million
Alex Rodriguez got exactly what he wanted when he and Scott Boras upstaged the Boston Red Sox run to the 2007 title, announcing he was opting out of his Yankees contract midway through the Fall Classic.
Conventional wisdom probably told the Yankees to run away here, but they didn't do things conventionally at the end of George Steinbrenner's reign. Instead, the Bombers signed Rodriguez to a 10-year, $275 million deal ... that ultimately didn't net them 10 years of production.
PROS: Literally don't win the 2009 World Series without him. This doesn't have to be a thought exercise. He was EVERYWHERE that postseason.
CONS: 2009 steroid drama, 2013-14 suspension, strange phasing out in 2016.
All in all, you have to do it again if you want that ring, still the most recent hardware this team has earned and the franchise's only post-Subway Series title.