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Gambling and the alpha dog

Gambling man

Editor’s note: This article appears in the June 19 issue of ESPN The Magazine.

There’s a famous gambling story about Michael Jordan. Actually, there are many famous gambling stories about MJ, but this one is my favorite. Back before NBA teams had grasped the rejuvenating power of chartered airplanes, the Bulls were waiting for their luggage in Portland when Jordan slapped a hunny on the conveyor belt: I bet you my bags come out first. Jumping on the incredibly favorable odds, nine teammates happily accepted the wager. Sure enough, Jordan’s bags led the rollout. He cackled with delight as he collected everyone’s money.

What none of the suckers knew, and what MJ presumably never told them, was that he had bribed a baggage handler to help him out. He didn’t pocket much (a few hundred bucks), and considering his net worth hovered around nine figures at the time, it’s safe to say he didn’t need the extra cash. But that didn’t matter. There was a chance at an easy score, and he took it.

Yes, the most cutthroat athlete of his generation loves to gamble, and even more than that, he loves to win. Should you be surprised? The qualities that once made MJ transcendent on the court — his legendary hypercompetitiveness, superhuman stamina, larger-than-life swagger and unwavering confidence — make the gambling crossover an obvious choice.

Now, not all top-tier superstars have the bug. Word is that Larry Bird, a renowned cheapskate, wagered only on postpractice shooting contests (which he was predisposed to win because, after all, he was Larry Bird). But Jordan was fundamentally more reckless. He played high-stakes golf — you may remember he once settled a seven-figure debt for $300,000 with a grateful hustler who felt compelled to write a book about it — and made at least one ill-advised trek to Atlantic City between playoff games.

I’m the last person to think that MJ’s hobby makes him as unsavory as a Bada Bing! customer. Too much has been made of his gambling “problem” over the years. Take Michael Leahy’s mean-spirited book, in which he salaciously recounts a 2001 blackjack blowout at the Mohegan Sun that included Rip Hamilton and Antoine Walker. Leahy made the night seem nefarious, describing how MJ fell behind by half a million before turning things around in the wee hours by playing two hands at a time, jabbering loudly and confidently all the while, working the dealer as if he were Bryon Russell. I happened to be there as well, plugging away at a $15 table about 25 feet away. What I witnessed was just three friends letting off steam.

Everything’s relative. Last summer, at my buddy Hopper’s bachelor party, we played blackjack at Mandalay Bay until 8:45 a.m., one of those blurry marathons where you wake up the following afternoon, heave a sigh of relief when you see your wallet (“I didn’t lose it!”) then scream happily when you glimpse the wad of hundreds inside. Women had flirted with us, pit bosses had sauntered over to “cool” us down. We hadn’t played for 25 G’s a hand, but we had risked a higher percentage of our net worth than MJ did in his Mohegan cameo, that’s for sure. It was my single best run in Vegas — and I didn’t have Leahy standing nearby jotting down unflattering notes.

We love to pick athletes apart, but what’s the big deal about their gambling so much? Look what happened last month. First, John Daly says he lost $50-60 million at the slots, and it becomes a national story. Then, Charles Barkley defends Daly, before casually revealing that he’s squandered $10 million in casinos over the years. Of course, the media blows up that revelation and excoriates him for being so irresponsible. What’s irresponsible about losing millions when you have more money than you’ll ever need? Playing with the house’s money is a way of life for these guys.

Watch an episode of MTV Cribs: For many celebs, it’s not just about making it; it’s about embracing the excess of making it. It’s about owning the biggest mansion and the most cars, being able to buy anything without someone saying, “Wait, you can’t afford that.” It’s about walking into a Ferrari dealership and having the salesman keel over with glee. It’s about buying a yacht even though you don’t particularly like water. It’s about wearing a different suit after every game. It’s about playing Madden on a 100-inch plasma instead of a 40-inch flatscreen. High-stakes gambling is just another piece of the excess package.

Casinos actually hold an allure beyond the action. With their elite gaming areas and impeccable security, they are some of the few public places where athletes can unwind without being badgered by starstruck fans. Call it an amusement park for the privileged, a place to let loose and be rich, where competitive juices can get a victimless workout. For a big-stakes guy, every night starts with the same vow: “I’m gonna kick ass.” If he gets down, he just knows he’ll win it back. If he’s up, he wants to be up more. If he didn’t possess this drive at the tables, he’d be one of those Rudy Gay types on the court, a player who drifts during games and doesn’t seem to care if his team wins or loses. Competitiveness isn’t a switch you can turn on and off.

That’s why these guys bring PlayStations on the road, why card games never end on charters, why who-can-make-the-first-halfcourt-shot contests break out at the end of every NBA practice. David Stern says he’s dead set against moving a team to Vegas because he’s afraid players will wager on NBA games. But if they want to, they can easily do that online. What he should be afraid of is that they’d be fodder for the high-roller hustlers in Vegas who make a killing in poker games and golf matches with overcompetitive multimillionaires.

History tells us there’s no shortage of those: Isiah Thomas played in high-stakes craps games at Thomas Hearns’ house; Jerry Stackhouse decked Christian Laettner during a poker game on the Pistons’ charter; Phil Mickelson won tens of thousands on World Series and Super Bowl bets as part of a consortium; Charles Oakley publicly threatened Tyrone Hill for being slow to settle a dice debt. For every story that leaks out, dozens of others are almost surely buried.

But no one can convince me it’s a bad thing. There has been a negative link between gambling and sports dating back 100 years, back when heavyweight title fights and the World Series were fixed. But that is a lot less likely to happen now: Professional athletes earn too much to be swayed by fixers. Still, fans are brainwashed to believe gambling is dangerous, that it’s a potential gateway to self-destruction, that it can destroy your life if you aren’t careful, that everyone is a few errant bets away from a lifetime of depressing Gamblers Anonymous meetings. Watch any TV show in which a character starts betting, and almost always, he loses control before the big “intervention” episode. Gambling is bad. Or so we’re told.

And then you see the 400 different poker shows on cable, gambling spreads in every newspaper, March Madness pools in every office, websites and magazines that have made a killing on the fantasy boom, scratch cards and lottery machines in every convenience store … Ummm, none of this is gambling? We refer to point spreads all the time — the Steelers are favored by six — and naïvely pretend they happen in some sort of vacuum, that there’s no correlation between the numbers and actual wagering. Everyone participates in this hypocrisy. It’s a more complicated version of the four college roomies who stand around a keg on a Friday night and slurringly argue about whether one of their other pals has a drinking problem.

Gambling is a part of sports; we may as well accept it. Maybe there are ways teams can actually use it to their advantage. For instance, Hopper once played blackjack in Vegas with Norv Turner, who spinelessly kept staying on 16 until my belligerent friend drove him from the table with a biting remark. After hearing that story, I thought Turner’s coaching career made infinitely more sense. What football player would be inspired by a coach who stays on 16?

If I owned a team, I’d insist on playing poker or blackjack with any coach or manager I was thinking of hiring. During Jordan’s Mohegan Sun all-nighter, I distinctly recall being impressed that Hamilton — still a young player who hadn’t done much — looked totally comfortable in the high-stakes section with MJ. Good sign for his future, I remember thinking. That poise made him one of the crucial players on the world-champion Pistons. Coincidence? You tell me.

As for Jordan, if I owned the Bulls and found out my franchise guy — the dude cashing my seven-figure checks every two weeks, the dude responsible for filling my stadium eight months per season, the dude who would make or break my dream of holding the Larry O’Brien Trophy — was bribing baggage handlers just to win a few hundred bucks … well, the news would warm my heart. That’s what alpha dogs do: They compete, they dominate, they don’t know when to quit. The surprise isn’t that there are dozens of gambling stories about Michael Jordan. The surprise would be if there weren’t any.

Bill Simmons is a columnist for Page 2 and ESPN The Magazine. His new book “Now I Can Die In Peace is available on Amazon.com and in bookstores everywhere.

Filed Under: Gambling

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Bill Simmons is the editor-in-chief of Grantland and the author of the New York Times no. 1 best seller The Book of Basketball. For every Simmons column and podcast, log on to Grantland.

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