After getting selected by the Los Angeles Clippers in the first round of the 2000 NBA Draft, Miles signed an endorsement deal with sports apparel company Jordan and featured on the cover of Sports Illustrated.
He even scored a brief career as a movie star. He was in 2002 comedy Van Wilder alongside Ryan Reynolds. Two years later he featured in The Perfect Score alongside Scarlett Johansson.
He was traded to the Cleveland Cavaliers and then moved to Portland after that on a large free-agency contract.
In 2006 he needed knee surgery and the Blazers tried to force him into retirement.
Portland did eventually cut him from the roster and paid out Miles' entire contract, including a $9 million salary for the 2009-10 season.
By that time Miles was already retired - against his will.
On the outer in Portland, Miles tried to resurrect his career at the Memphis Grizzlies. He played 34 games during the 2008-09 season.
It was over when he failed to win a roster spot in Charlotte the next season.
Then came a series of legal problems and bad investments.
As reported by the News-Democrat, Miles' bankruptcy claim included child support debts of $20,000. He lost $100,000 in a real estate deal in California. Another real estate deal became embroiled in a series of lawsuits.
He also submitted to the court that he has tax debts with the Internal Revenue Service of $US282,041.
Reports from Miles' earlier playing days suggest the damage to his personal wealth was committed well before his retirement.
Those reports included claims Miles had a habit of rewarding himself with diamond jewellery.
Miles claims in the court documents the majority of his debts are business-related, not personal expenditures.
As simple as that, his fortune was gone.
It's a very common story across the NBA.
Former Orlando star and NBA players' union vice president Adonal Foyle says up to 60 per cent of NBA players now file for bankruptcy in their first five years out of the game.
Foyle told The New York Post recently there is genuine fear among players about "the lottery of going broke".
"Lots of players are having financial trouble, but they won't talk about it," Foyle said.
"There's a lot of fear. Guys are vilified. They're waiting to see who goes into the lottery of going broke.
"Lots of guys are having trouble.
"But they won't talk about it. They think, 'I don't want to be one of those guys,' and they're hiding it."
He told The News-Democrat the easiest way for players to avoid squandering their wealth is to attend university to both learn how to manage their money and simultaneously discover a path for what comes after their basketball careers.
"It's difficult for players, especially those who didn't go to college, to be prepared to understand the business side of what they do," Foyle said.
"They need to understand that what they do isn't just on the basketball court, they are the CEO.
"They need to find the right people to watch over their money and then watch those people. It's a lot of work."
"College gives you a chance to figure out what you are interested in. My parents asked me when I was still playing what I wanted to do after this was over, and it got me thinking about it," Foyle said. "Players need to ask themselves, 'What's the next step?'"
