By Jon Wertheim
October 25, 2010

1. Reckless gamble: I was talking to a prominent men's doubles player recently about pressure. Playing for the Wimbledon final, he asserted, was nothing compared to the stress of playing a pro-am match in the Huggy Bear tournament. Come again? The Huggy Bear is the Skull and Bones of tennis events, a private affair held before the U.S. Open on private courts in the Hamptons. No TV, no sponsors, a small handful of fans. But some of the most intense matches of the year.

The Huggy Bear paired Wall Street royalty with tennis pros. And while the event raised tens of millions for charity, it also featured gambling. Heroic gambling. There are stories of six-figure wagers on single points, of hedge fund and LBO titans screaming at the accomplished pros over botched volleys. (How much money are we talking? Consider this: Ray Charles and Faith Hill have allegedly performed as musical guests.) My friend the doubles player claims that a few years ago his partner asked to confer between points. The partner leaned in and then said: "How about making a f$#!@&* first serve before I lose another 100 grand? Think you could do that for me?"

Oh, yeah. The de facto tournament director: Teddy Forstmann. "Huggy Bear" supposedly is a nod to one of Forstmann's brothers, known for his fondness for hugging.

I kept thinking of this story last week. If you know about the Huggy Bear (or, for that matter, read Barbarians at the Gate), Forstmann's admission that he placed a sizable wager on a sporting event is something other than shocking. What is shocking is that he was foolish enough to bet a) on tennis and b) on a player he represents. As the figure who essentially owns IMG -- the powerful marketing giant -- this shows an alarming absence of judgment. IMG doesn't merely represent players but runs tournaments, handles the branding of Wimbledon and packages television rights. The conflicts are disconcerting enough without the head of the company placing bets on specific players.

What's more, betting scandals have rocked in recent years. So much so, that there is a specific anti-corruption, pro-integrity task force in place. So much so, that credentialed personnel at most tournaments have to sign a form like this, promising not to gamble. So much so, that a WTA player was recently fined and suspended, simply for failing to report having been approached by a potential match-fixer. When the head of IMG so openly flouts the rules, it does terrible damage to the credibility of these anti-corruption policies. Every tournament volunteer has to sign a blood oath that he or she won't wager -- but the head of IMG can plunk down $40,000, as Forstmann acknowledged doing?

Maybe most disconcerting is the collateral damage. Forstmann's wager involved Roger Federer and, according to reports, was placed after Forstmann had conferred with Federer and received a status update. Let's be unequivocally clear: At least as the facts now stand, Federer did nothing wrong. He's entitled to tell a friend how he's feeling. There is no indication or suggestion he knew that Forstmann would be wagering on his performance. Still, that Federer's name has even come up in this context is disgraceful. Federer has spent his career as the consummate ambassador for the sport, a champion in every sense of the word, with an unimpeachable record. The one time he gets "TMZ'd," the one time there is a whiff of scandal, it's because of his own management firm? You'd think a businessman smart enough to make billions would know that you don't risk tainting your prized asset like this.

To his credit, Federer has taken questions on this unpleasant episode. And absent more information, we ought to divorce him from Forstmann's colossally bad judgment. But he deserves better. Not bettor.

2. Federer ties Sampras: As for Federer's tennis, he was in action last week in Stockholm. Sure, this was an appearance fee special, late in the season. But credit him for playing and playing well, tying Pete Sampras with his 64th career title. OK, beating Florian Mayer in the final of a non-mandatory tournament isn't likely to make the short list of Federer's career highlights. But if it gives him some confidence -- as it should -- heading into the last two indoor events of the season, it will have been well worth it. Sometimes winning a smaller title under low-intensity light is precisely what a player needs to start a significant streak.

3. Vika for victory: At least for American sports fans, it seems that not a day goes by that we don't learn a bit more about the severity of concussions and the potentially catastrophic mix of head injury and physical exertion. In retrospect, Victoria Azarenka's episode at the 2010 U.S. Open -- she hits her head before a match, insists on playing, takes the court in brutal heat, and passes out on the court -- is horrifying. Fortunately, Azarenka was not seriously injured that day. And her game has shown no ill effects. She took the Kremlin Cup in Moscow last week, beating Maria Kirilenko in the final and qualifying for the year-end shindig in the process. Given the shakiness on the upper rungs of the WTA corporate ladder, Azarenka is on the short list of new players to fill the vacuum.

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