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As soon as an athlete goes pro, people in search of handouts tend to stretch the definitions of family and friends. When Hunter went to his hometown of Pine Bluff, Ark., for his grandmother's funeral last August, he found Old St. James Baptist Church packed, the line of cars outside stretching for blocks. "But my grandma didn't know anybody," Hunter says. "She just lived at home." When he stepped outside the church, people "came running, all dressed up, chasing after me," Hunter says. "They were throwing CDs, projects, letters.... They were yelling, My sister's brother went to school with you!"
A different but equally potent pressure operates in the workplace—the clubhouse, the locker room and the team plane. "For rookies, it's like an unspoken initiation," says Strickland. "You're trying to get in good with the veterans, so you go beyond your means. You drive the nice car, splurge on a house."
The veterans don't mind giving explicit instructions. "I got ripped my first three years in the NFL, every day," says Tubbs. "I got on planes with a cassette player, and [a teammate] would tell me, 'They make CD players. You're in the NFL now.'"
Perhaps the upper limit on spending was set by the famously profligate Shaquille O'Neal, who—according to a document obtained by the Palm Beach Post during O'Neal's canceled divorce filing in January 2008—spends a total of $875,015 each month, including $26,500 for child care, $24,300 for gas and $17,220 for clothing. But O'Neal, who also has been known to fund charities anonymously and cover medical bills for complete strangers, has the wherewithal to remain solvent.
Imitators have been less fortunate. When former NBA guard Kenny Anderson filed for bankruptcy in October 2005, he detailed how the estimated $60 million he earned in the league had dwindled to nothing. He bought eight cars and rang up monthly expenses of $41,000, including outlays for child support, his mother's mortgage and his own five-bedroom house in Beverly Hills, Calif.—not to mention $10,000 in what he dubbed "hanging-out money." He also regularly handed out $3,000 to $5,000 to friends and relatives. (Along with Ismail, he enlisted as both a Slamball coach and a Pros vs. Joes participant last year.) Former big league slugger Jack Clark filed for bankruptcy in July 1992 while still playing, listing debts of $6.7 million and ownership of 18 cars—17 of which still had outstanding payments.
Financial advisers have come to call it "the problem of the $20,000 Rolex." If a 22-year-old spends $20,000 on a watch or on a big night out at a nightclub, that money is either depreciating or gone. "But if they invested in a five percent, Triple A insured, tax-free municipal bond for a period of 30 years," money manager Seymour says, "that $20,000 would be worth $86,000 at that tax-free rate of return. And needless to say, they buy more than one $20,000 Rolex."
Four years ago future NBA Hall of Famer Scottie Pippen unsuccessfully sued his former law firm for allegedly losing $27 million of his money through poor investments. (He had earned about $110 million in salary alone over a 17-year career.) In February 2007—around the same time as Pippen's failed NBA comeback attempt—the Missouri Court of Appeals upheld a ruling that the player owed U.S. Bank more than $5 million in principal, interest and attorneys' fees from a dispute regarding a Grumman Gulfstream II corporate jet that he'd purchased in 2001.
In an era in which banks are lambasted for using taxpayers' money to fly their executives on luxury private planes, it's a smart bet for players not to use their own cash to do the same. "In this economy, especially, the goal shouldn't be living that kind of lifestyle or trying to get richer," says West. "It needs to be about trying to maintain the wealth."
SOMETIMES, THOUGH, a jock just can't shake the temptation to try to hit the jackpot. Butowsky believes that "there's something in an athlete's mentality" that drives him to swing for the fences financially—usually at his own peril. "The solution to the problem is, without a doubt, education," the adviser says. "Change won't happen until grown men start wanting to learn."
Old habits die hard. Despite all his dreadful experiences, and lessons absorbed the hard way, not even Ismail is done yet. This time around, the project in which he's invested $250,000 is a special mouth guard—available online for $79.95—that's designed to help the body "physiologically perform at the highest level," he says. The science behind it involves relieving pressure on the temporomandibular joint and holding the jaw in an "optimal" position. (Ismail made the investment before he began consulting with Butowsky.)