No. 2: Cliff Lee, $120 million/5 years
In 2011, Cliff Lee returned to Philadelphia on a five-year, $120 million deal, but sadly was never able to finish out the end of the deal due to an elbow injury.
Over his first three seasons back with the Phillies, the 2009 postseason star was as dominant as ever. He crossed the 200 innings mark in all three seasons, finishing with a 2.80 ERA, 1.05 WHIP, and 667 strikeouts in his 666 1/3 innings. From 2011 to 2013, Lee had a 17.7 fWAR, the fourth-best pitcher WAR in the majors.
The lefty earned two All-Star nods, in 2011 and 2013, and finished third and sixth in NL CY Young voting in those years, respectively.
After barely missing out on a World Series championship during his 2009 stint in red pinstripes, Lee only got one more chance in the postseason with the Phillies, and it didn't go well. Despite his dominant 2011 regular season, his NLDS appearance was one to forget when he gave up five runs on 12 hits to the St. Louis Cardinals.
Lee battled injuries to start the fourth year of his contract in 2014 and only threw 81 1/3 innings for the Phillies that season. Dealing with a flexor tendon tear, Lee didn't pitch at all during the fifth year of his contract and the Phillies declined to retain the former ace for an optional sixth season and bought him out for $12.5 million.
What began as a glorious return to Philly ended up in shambles — but Lee still got paid.