tloineThat’s an investment I can’t argue with…

It’s pretty hard to find the most ridiculous part of this terribly sad story about Antoine Walker and how he squandered $110 million of earnings in 12 years, but I’ll give you some candidates.

Walker signed a six-year, $71 million guaranteed contract in 1999. 10 years later, he’s in the hole about $4 million to creditors.

I’m guessing this didn’t help:

Living at the Bishops Forest condominium complex in Waltham during the Celtics season, Walker turned the pavement surrounding his home into a virtual luxury car lot – two Bentleys, two Mercedes, a Range Rover, a Cadillac Escalade, a bright red Hummer. Often, the vehicles were tricked out with custom paint jobs, rims, and sound systems at considerable added expense. He also collected top-line watches – Rolexes and diamond-encrusted Cartiers.

Then, there were the custom-tailored suits – closets full of them, including the set he ordered for his first playoff run in 2002, enough so he wouldn’t wear a suit more than once during the postseason run. When the Celtics officially hired Jim O’Brien as head coach in 2001, Walker had his tailor make three suits and presented them to O’Brien.

I’m guessing this didn’t either:

Gambling has long been a favorite form of entertainment for Walker. After a 2001 exhibition game at Mohegan Sun, Walker once reportedly played $15,000 hands with Michael Jordan during an all-night gambling session where estimates of money lost and won totaled several hundred thousand dollars. Prior to the 2003-04 season, when Celtics general manager Danny Ainge called Walker to tell him he had been traded, Walker was engrossed in a high-stakes blackjack game at Mohegan Sun.

I wonder if Antoine’s mother, who put him through private Catholic school in Chicago instilled the value of a dollar with him:

Walker’s mother, Diane, said her son does not have a gambling problem. She added that “he doesn’t party any more than the next person’’ and “what you do with your life is your business.’’

“Antoine doesn’t owe anybody any explanation,’’ said Diane Walker. “He’s not out here hurting anybody. He’s trying to live his life peacefully. That’s all he’s doing . . . My son is young. Why can’t he just enjoy life, go where he wants to go?’’

When asked about her son’s recent, well-documented financial and legal problems, Diane Walker stood stoically outside her front door. She made a sweeping gesture toward the mansion, moving her hand past a giant brick “W’’ embedded in the driveway.

“Antoine is doing great,’’ said Diane. “I have my home. He has his home. If he’s doing so bad, then how could we still be here?’’

But if I had to pick one problem that ‘Toine had, it wouldn’t be the cars, the houses, the gambling, or the 70 person entourage… It’d be the venture capital service.

Walker has also tried his hand at venture capital investing with Walker Ventures LLC and in real estate with AW Realty LLC. Walker Ventures appears on court documents as a codefendant in the American Express and J.P. Morgan Chase civil cases. Walker’s realty company is listed as the owner of several Chicago-area properties, including his mother’s home, once valued at $6 million but now worth a quarter of that, or less, according to more recent estimates.

Seriously? Seriously? How does venture capital even get brought up to Walk?

Hanger-On: Yo, Antoine, I got a killa tech start-up that’s going to blow da roof when it IPOs…
Antoine: For real? You should send that over to my boyz running Walker Ventures LLC, have the roll the numbers on it.
Hanger-On: Fo’ ‘Sho. This thing’s got all the cats in Silicon trying to get a piece, hard.
Antoine: Silicon? Damn, son — that’s all you needed to say.

I don’t want to be too hard on Walker, because he also gave a ton of his money away to charities and was kind to teammates, often times picking up the check on dinners, team outings, and other things professional athletes do when they want to waste money, but I wish this kind of thing wasn’t something that you just rolled your eyes at. If it wasn’t so predictable, it’d be sad.

At least he’s got that collection of Rolexes and diamond-encrusted Cartiers to fall back on.

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