Carlos Pena 3yr/$24M (2008)
Carlos Pena originally signed with the Devil Rays in 2007 on a 1 year 'prove it' deal after bouncing around a few teams before the age of 30. In 2007, Pena batted .282 hitting 46 home runs with 121 RBIs and 99 runs. Pena was 9th in MVP voting that year and was also a Silver Slugger. This is probably the best case scenario for Pena.
In 2008, the Rays offered Pena a big extension in their regards and signed him to a 3yr/$24M contract. Over those next 3 years, Pena averaged 95 RBI, almost 33 HR (leading the league in 2009 with 39) and 77 runs. Pena also received his only all star nod in 2009 with the Rays before moving on to play with 4 other teams (and coming back to the Rays for a year). This contract for the money was a massive win for the front office.