30 highest career MLB salaries

Aug 12, 2016; Bronx, NY, USA; New York Yankees designated hitter Alex Rodriguez (13) waves to the fans after playing his final game as a Yankee against the Tampa Bay Rays at Yankee Stadium. The Yankees won 6-3. Mandatory Credit: Andy Marlin-USA TODAY Sports
Aug 12, 2016; Bronx, NY, USA; New York Yankees designated hitter Alex Rodriguez (13) waves to the fans after playing his final game as a Yankee against the Tampa Bay Rays at Yankee Stadium. The Yankees won 6-3. Mandatory Credit: Andy Marlin-USA TODAY Sports /
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Jul 21, 2006; Chicago, IL, USA; Boston Red Sox MANNY RAMIREZ against Chicago White Sox in Chicago at U.S. Cellular Field. The Red Sox won 7-2. (Photo by Matthew Kutz/Sporting News via Getty Images)
Jul 21, 2006; Chicago, IL, USA; Boston Red Sox MANNY RAMIREZ against Chicago White Sox in Chicago at U.S. Cellular Field. The Red Sox won 7-2. (Photo by Matthew Kutz/Sporting News via Getty Images) /

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.