Kobe Bryant, Los Angeles Lakers
Upon retiring in 2016, Kobe Bryant made a record $323 million in career salary earnings, and while Los Angeles probably doesn't regret a large part of that, it was the latter chunk of paying for his time at the Staples Center that probably makes them wince. For his final two seasons, he signed a two-year $48.5 million contract extension. Sadly, they plagued by injuries that sidelined the legendary player. To put it plainly: the household name was paid like a superstar and played like anything but.