Johan Santana

In 2012, when Santana pitched the first no-hitter in Mets history, it also may have ended his career. After missing the 2011 season, he threw 134 pitches in the no-hitter. Thereafter, he had an 8.27 ERA in the last 10 starts of that season, which also happened to be the end of his career.

The Mets paid him $37.3 million after the injury, including a buyout, but the team also owed him $5 million, at 1.25% compound interest, seven years after each year of the deal. Another long deal for the Mets, but at least this one ends in 2020.