Fansided

30 highest career MLB salaries

By Nathaniel Reeves

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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WASHINGTON, DC – AUGUST 17: Johan Santana #57 of the New York Mets in action against the Washington Nationals at Nationals Park on August 17, 2012 in Washington, DC. (Photo by Patrick McDermott/Getty Images)
WASHINGTON, DC – AUGUST 17: Johan Santana #57 of the New York Mets in action against the Washington Nationals at Nationals Park on August 17, 2012 in Washington, DC. (Photo by Patrick McDermott/Getty Images) /

27. Johan Santana, $155,997,269

Santana is one of many examples of a huge pitcher contract backfiring, as the two-time Cy Young Award winner faded later in his career with the New York Mets.

Originally a member of the Houston Astros organization, Santana was selected by the Minnesota Twins in the 2000 Rule 5 Draft. The move paid off massively for the Twins, as Santana would develop into one of the best pitchers in the Majors four years later with a 2.61 ERA and strikeout rate of 30.1 percent to handily win the AL Cy Young Award while making just $1.6 million.

Two years later, Santana won the pitching triple crown and another Cy Young Award, although his salary only increased to $9 million. As Minnesota was unlikely to afford whatever Santana would end up commanding in free agency, it traded him to the New York Mets prior to the 2008 season, and the two sides quickly agreed on a six-year, $137.5 million deal.

Santana posted a strong 5.3 WAR campaign in his first season with the Mets and was solid enough in both 2009 and 2010. Unfortunately, Santana underwent shoulder surgery in September of 2010 and was only able to throw another 117 innings before retiring, although he did toss the first no-hitter in Mets history in 2012.

A pair of comeback attempts with the Baltimore Orioles and Toronto Blue Jays could have pushed Santana further up the list, but he was unable to reach the Majors again due to various injuries.

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