Bosh is far from the only former athlete to reach a roadblock when it comes to finances, especially after retiring from the game. A viral Sports Illustrated feature from 2009 cites a humbling statistic: "By the time they have been retired for two years, 78 percent of former NFL players have gone bankrupt or are under financial stress because of joblessness or divorce."
That goes for basketball players like Bosh as well: "Within five years of retirement, an estimated 60 percent of former NBA players are broke."
Nnamdi Asomugha, who spent 11 seasons in the NFL, speculates that this happens, at least in part, because of the conflicting advice given to players. "I majored in finance at the University of California at Berkeley, but even that didn't prepare me for protecting my money as a professional athlete," Asomugha told Wealthsimple.
For athletes, it's extremely tough to trust people with your finances. It's so easy to be victimized. When I hear about a player losing his money, I'll rarely, if ever, point a finger at the player because I know how difficult it is. It's not always, 'Look at this idiot who got paid all these millions of dollars and lost it all.' It may be more like, 'This naive kid with a million things going on in his life put his faith in the wrong people.' I know because I was that person.
For Asomugha, that truth meant developing a back-up plan well before he was finished with football, a realization that came during his second year in the league. "It was a clear message that, as a player, you're not really in control of your destiny and the way you make a living," he says.
Bosh's situation is especially tough because he anticipated many more years playing basketball before retiring.
"They tell you, 'Prepare for the future,' but that was impossible,'' Bosh says. "I'm thinking, 'Hey, I'm trying to win NBA championships here. I'm all-in on that. I can't be thinking about the future right now.'''
He's still hopeful for another chance to play basketball. But no matter how his career shakes out, he'll soon become well-versed on his finances as well.
Like this story? Like CNBC Make It on Facebook!