34. Troy Tulowitzki – Colorado Rockies, Major League Baseball:
The now-34-year-old Tulowitzki signed a ludicrous 10-year, $157,750,000 deal averaging $15,775,000 per year and $97,376.54 per game in late 2010.
The unreal shortstop had torn up the National League for several years. But he unfortunately ran into injuries. He hurt his groin, rib, and hip in successive seasons. The onetime star was traded to the Toronto Bluejays in 2015. He then hurt his quad, hamstring, and ankle in a second three-year stretch. He now earns the league minimum for the New York Yankees. This did not end up being a good deal.