Evan Longoria 6yr/$100M (2012)
To be clear, the specifics that are being mentioned here is his six year extension that Longoria received from the Rays. The total of his two contracts came out to about 15 years and a total of $144 million which is a still a lot of money to the Rays standards but also a steal to many other teams standards. Since his debut in 2008, Longoria may be the first name that people think of when they think of the Tampa Bay Rays. In his 10 years as a Ray, Longoria was a Rookie of the Year, won 3 Gold Gloves, one Silver Slugger, was a 3 time All Star and finished with MVP votes 6 times.
In 2018, Longoria was traded to the San Francisco Giants for Christian Arroyo (later traded to the Guardians), Stephen Woods (later traded to the Royals), Matt Krook (later selected by the Yankees in the Rule 5 Draft) and Denard Span (played a total of 43 games for the Rays). Overall in terms of player production, the Giants were the winners of the trade but if saving money is the name of the game, the Rays came out on top. From 2018 to the end of his contract, Longoria was owed $81 million across 5 years. While the player himself might be missed by Rays fan, the money owed will not be missed by the front office.