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As boxing history has shown us, it's that many of the biggest stars of the sport will go broke when they hang it up.

Only a few has escaped that fate such as Leonard and De La Hoya comes to mind. Hagler is doing well or at least isn't broke. Ali is doing well and so is Naseem Hamed.
Oscar isn't doing as well as ya'll think/wish..
Financially he is
No he isn't.

Dude is a damn junky..
This article from a couple of weeks ago says otherwise. Worth more than Floyd

Reports: Oprah Winfrey, Oscar De La Hoya, Floyd Mayweather Jr., even Matt Damon would like to buy Clippers | ProBasketballTalk
Floyd overhype himself and its all part of the smoke and mirror al haymon creates. Floyd thinks he got millions.

Goldenboy > Prettyboy

Floyd fakes a promotion. Oscar got a real one
schaefer is golden boy...not Oscar...

Floyd has passed Oscar a while ago.