Charlie Morton 2yr/$30M (2019)
The Charlie Morton saga might be one of the most painful in Rays history. Coming off a 15-3 season with the Houston Astros, Charlie Morton signed a two year deal with the Rays. Surprisingly to some, Morton was able to replicate his stellar season all star season with another one, going 16-6 with a 3.03 ERA, a second all star appearance, and a 3rd place finish in the Cy Young voting. Morton threw 9 games in 2020 but what happened after is what hurts the most.
In typical Rays fashion, they looked to save money any way they could in 2021. This included declining Morton's $15 million team option and letting the dominant pitcher test free agency. The worst part of the entire situation is that Morton ended up signing with the eventual World Series champion Atlanta Braves for a total of... you guessed it. $15 million. Morton showed minimal signs of declining and the Rays problem late in the season and into the postseason was a lack of starting pitching. Charlie Morton leaving the Rays will forever be one of the biggest 'What ifs?' in recent Rays history.