Ben Zobrist 4yr/$18M (2010)
Ben Zobrist had one of the longer tenures in Rays history but at the same time only holds the 11th biggest contract in Rays history. Zobrist played 9 years for the Rays and did fairly well with them. Zobrist's best year came in 2009 where he batted .297 over 152 games and had 27 home runs, 91 RBI and drew 91 walks. Zobrist was selected to the all star game that year and also finished 8th in MVP voting.
That great year for Zobrist earned him a 4 year extension worth $18 million. To the Rays, this is a significant amount of money but in hindsight, this was a steal. To put it into perspective, the Rays offered Zobrist his extension when he was 29 years old, the peak of a baseball player's ability. In 2016, the Chicago Cubs offered Zobrist a 4 year $56 million contract at the age of 35. The slash lines of Zobrist on the Rays versus the Cubs are extremely similar so it is safe to say the Rays won this deal.