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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Oct 29, 2016; Chicago, IL, USA; Chicago Cubs former pitcher Greg Maddux waves to the crowd before the ceremonial first pitch before game four of the 2016 World Series against the Cleveland Indians at Wrigley Field. Mandatory Credit: Tommy Gilligan-USA TODAY Sports
Oct 29, 2016; Chicago, IL, USA; Chicago Cubs former pitcher Greg Maddux waves to the crowd before the ceremonial first pitch before game four of the 2016 World Series against the Cleveland Indians at Wrigley Field. Mandatory Credit: Tommy Gilligan-USA TODAY Sports /

29. Greg Maddux, $153,845,000

With one of the most lucrative free agent contracts of the early 1990s under his belt, Maddux remains one of the highest-paid pitchers in MLB history.

Maddux spent the first seven years of his big league career with the Chicago Cubs, earning a pair of extensions worth $6.4 million from 1990-1992. While Maddux was solid throughout his time in Chicago, a 20-11 campaign with a 2.18 ERA and 7.0 WAR in his contract season helped him win the Cy Young Award and garner a lot of attention in free agency.

The Atlanta Braves then signed Maddux to a five-year, $24 million contract, followed by a $57.5 million extension that lasted through the 2003 season. Maddux lived up to the pricey contract by winning three straight Cy Young Awards upon his arrival, and helped the Braves win the 1995 World Series.

As Maddux was still pitching effectively enough by the end of his contract, Atlanta signed him to an additional $14.75 million deal in 2003, the highest single-season earning of his career. A reunion in Chicago for $24 million over thee years followed, and Maddux closed out his career in 2008 with the San Diego Padres on a pair of one-year deals worth $20 million.

Maddux posted no worse than a 3,18 ERA from 1988-2002 and was inducted to the MLB Hall of Fame in 2014, showing his career earnings of over $153 million were well worth it.