30 highest career MLB salaries
8. Manny Ramirez, $206,827,769
Boston took a gamble by offering Ramirez a then-record contract in 2000, but he proved to be well worth the money by helping Boston to a pair of World Series titles.
Ramirez debuted with the Cleveland Indians in 1993 and quickly developed into a terrific middle of the order presence two years later with a string of five straight seasons with at least a 140 wRC_ heading into free agency. Cleveland offered Ramirez a seven-year, $119 million deal that would have made him the highest paid player in November of 2000, but he decided to test the market.
That choice paid off, as Ramirez earned a 10-year, $200 million contract with the Red Sox the next month. Ramirez became an even better hitter in Boston with a 181 wRC+ in his first season to set off a string of eight straight top 10 finishes in the MVP.
In the final summer of the lengthy deal, Ramirez was traded to the Dodgers, who gave him a two-year, $45 million contract in the following offseason. A 50-game PED suspension in 2009 hurt Ramirez’s chances of finishing his career on a high note, and he only managed a series of small deals with three different teams before retiring in 2014.
Ramirez finished his storied career with 555 home runs and 66.3 WAR, and will always have a special place in Red Sox history despite the cloud of steroids.