Blake Snell 5yr/$50M (2019)
This Blake Snell contract is interesting because the Rays are not the one paying the bulk of the money. However, it is one of the highest amounts of money that the Rays intended on giving out. In 2018, Blake Snell won the AL Cy Young award with one of the most dominant seasons in recent history. Snell finished the year 21-5 with a 1.89(!) ERA, a 217 ERA+ (where 100 is league average) and 221 strikeouts over 180.2 innings. This amazing season warranted an extension that reflected that and that is exactly what Snell got.
When you mention Blake Snell to any Rays fan, the first thing that comes to mind is not the Cy Young, but instead, game 6 of the 2020 World Series. Snell was dominating the Dodgers and had thrown 5.1 innings with 2 hits, 1 earned run and 9 strikeouts. Along comes Kevin Cash to take Snell out of the game despite Snell's performance because it was the third time through the order. Whether or not this was the right decision will be forever debated but the reality of the situation is that it happened.
Only a few weeks later, Snell was traded to the San Diego Padres for a package of Luis Patino, Cole Wilcox, Francisco Mejia and Blake Hunt. Patino looks to be a staple in the rotation in 2022 and Mejia saw significant time in the big leagues in 2021. The Snell trade was not the worst deal in the world because of how the Rays initially structured the extension. Snell is owed the following money in years from 2019: $1M, $7M, $10.5, $12.5 and $16M. Should the Padres keep Snell the rest of his contract, he will be paid $39M from the Padres and only $8M from the Rays. Given the turmoil at the end of 2020, this was a good deal to make.