Outfielder Milton Bradley should have probably had a better career than he ended up with.
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For a hot second, it was all working out. Cleveland traded for Bradley in 2001, hoping he could replace Kenny Lofton. Replacing Lofton is not a small order, considering he was one of the most dynamic leadoff hitters in baseball history. But by 2003, it looked like Bradley was on his way to doing just that: In 377 at-bats he had a 147 OPS+, including a .421 OBP and 10 HR. He also stole 17 bases. Bradley’s numbers would have been better, but he lost the last six weeks of the season to injury. Cleveland liked what they saw, and that winter signed him to a $1.73 million, one-year contract.
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But as talented as Bradley was, he was a notoriously difficult personality. It was a problem that plagued him in Montreal and continued in Cleveland. In the Spring of 2004, he was involved in a series of on and off field incidents that forced Cleveland to trade him to the Dodgers for pitching prospect Andrew Brown. It was a terrible trade. Cleveland also sent outfield prospect Franklin Gutiérrez to LA, who would develop into a very good defensive outfielder. Andrew Brown would only ever throw 10 innings in Cleveland. Oof.
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Bradley would have a couple more good seasons, including an All-Star selection in 2008 with Texas, but he was hounded by injuries and personality clashes that continually sapped any real momentum in his career. He was out of baseball by mid-2011.
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Worth noting: If Bradley stayed with Cleveland in 2004, he would have been part of a very good outfield along with Grady Sizemore, Matt Lawton and Coco Crisp. Granted, it probably would not have helped the team improve on their 80-82 record–Cleveland’s starting pitching was a mess–but still. They had something good there.