Manny Ramirez

The Red Sox will be paying Ramirez until he’s 54 years old, thanks to $32 million in deferred money over 16 years. They started paying $2 million per year in 2011 and will do so until 2026, 18 years after Ramirez was traded to the Dodgers, who also paid him long after he was released in 2010.

Ramirez collected $3.3 million in 2011 and 2012, plus $8.3 million in 2013. He made over $10 million in salary two years after his career had officially ended, which is a lot more than most players make in their entire careers.