Cigar Aficionado

Former NFL quarterback Steve Bartkowski has just finished a round of golf at the posh Waialae Country Club in Oahu, Hawaii. He's unwinding with a cool drink and paying off a few bets. Glancing up at the TV screen, he sees a PGA match in which one of the pros appears pressured to sink a six-foot putt. A pal of Bartkowski's, watching the action unfold, says, "That's not pressure. If he finishes second, who cares? His money isn't on the line. Pressure is when you have to sink a six-footer to win a $100 Nassau, and it's your $100."

That gets Bartkowski thinking about how cool it would be to have a golf event in which a lot of cash would hang in the balance, and sinking that six-footer (or not) would have real consequences. The idea gestates for several years, a few zeroes are added to the $100, and by 2005 Bartkowski has put together a handful of investors and organizers to run the richest tournament in golf history. Big Stakes Match Play is born.

The idea is simple: 128 teams of two golfers each put up $100,000 and play a four-ball match-play single-elimination tournament (each team counts its best score per hole, and the players compete on holes rather than strokes as in the Ryder Cup). Whichever team wins the majority of 18 holes goes on to the next stage of the event, while the loser is eliminated. Eventually, the last two surviving teams compete for a grand prize of $3 million.

Sounds sweet, but in the end, only 64 teams pony up the $100,000 entry fee (in almost every case it's put up by a sponsor) to play in the May tournament. Nevertheless, Bartkowski and his group keep the first-place prize at $3 million and cut corners on the runner-up awards—doling out a total of $6.4 million, including consolation prizes. The first-prize figure for this six-day event is suitably large enough that it draws several high-rolling team sponsors, including NBA legend Michael Jordan, football pros Barry Stokes and Ross Verba, and professional gambler/former World Series of Poker champ Russ Hamilton, who is representing the online poker site UltimateBet.com (which put up the $100,000 for its team). Not content to angle for a mere $3 million, Hamilton blows into the dusty Nevada town of Mesquite (where the tournament is being held) with a Bellagio shopping bag full of banded Benjamins. "There's $100,000 in the bag," he says flatly. "But if we use that up, I'll bring more. No problem. As long as we can get the best of it, we'll put down lots of money."

Carrying the bag of dough is Hamilton's right-hand man, Jeff Friedman. Slender, curly-haired and slightly wired, Friedman is a world-class golf gambler in his own right. Hamilton charged him with scouring the country to find the best possible twosomes to compete in the event and bring home the millions. A man with deep connections in the 18-hole world, Friedman was initially told to find the four best golfers possible. He did and reported as much to Hamilton. "Now," Hamilton told him, "narrow it down to the top two. I never did want four golfers. I just wanted you to have some options."

Friedman wound up recruiting John Douma and Mikkel Reese, a pair of blond-haired, meaty-faced mini-tour pros from Arizona (they look so much alike, and play so similarly, that opponents take to calling them The Clones). Conforming to Big Stakes rules, Douma and Reese have not been classified as PGA A-3 players for the last three years, are at least 25 years of age, and do not have fully exempt status on any of several major tours. The guys know each other as competitors on the sub-PGA Gateway Tour and clearly respect each other's game.

Hamilton's convinced that he's got the best horses in this particular race, and others agree. One night before the opening tee-off, at the Calcutta (in which bettors bid on the teams they think will win the tournament), Hamilton's guys go for $4,500, more than any other twosome. He views that as a good sign, which is underscored when Friedman tries to spread around some of the banded hundreds and finds no takers. With a shrug that doesn't quite hide his disappointment, Friedman stashes the money in a lockbox at the hotel and figures that nobody wants to bet against a favorite.

The next morning, Hamilton heads to Los Angeles, tending to some gaming business of his own, and Friedman is in charge of overseeing the team and making bets. Once again, he has no takers. Considering the split—25 percent for him, 25 percent for each of the golfers and 25 percent for Hamilton/UltimateBet—he says, "It's a lot of money. Even if you're Russ Hamilton."

That said, Friedman's not sure how well his golfers will handle the pressure of playing for more money than they have ever seen in their lives. On the one hand, he believes that they should be a little more on edge than they appear as they get set for the first tee at the CasaBlanca Golf Club in Mesquite. A par-72 course, CasaBlanca is nationally ranked and outfitted with cascading waterfalls, arroyos and a number of newly installed sand bunkers. On the other hand, Friedman kind of contradicts himself when he tells them to enjoy themselves, stay loose and play their game.

Several holes in, while watching Reese and Douma struggle to stay even, as one of their opponents seems preternaturally incapable of missing 30-foot putts, Friedman reaches a disturbing conclusion: "Either I severely underestimated the field or we've gotten extremely unlucky with the team we've been picked to go up against."

Maybe it turns out to be a little bit of both. While the UltimateBet team shoots a stunning 10 below par—in a round highlighted by impressively precise short games—the killer score is not enough to win. The duo is eliminated in heartbreaking fashion on the final hole.

The next afternoon, I see Jeff Friedman walking around the CasaBlanca Hotel lobby and carrying a leather bag across his shoulder. He does not look the least bit disturbed by the loss; he is, after all, a lifelong gambler and has had stranger things happen. "This is Russ's money," he says, patting the bag. "I've just got to get the [UltimateBet-logoed] golf bags back from the guys and I head to Vegas, so I can return everything. Nobody here wants to gamble, so there's nothing left for me to do." Asked if he's surprised at the dearth of action, Friedman shrugs and acknowledges that it turned out to be a blessing. "Otherwise we'd be out another $100,000."

The dynamos who beat the UltimateBet team happen to be backed by Michael Jordan. No surprise, then, that he'd put his money on a couple of winners. The team's stronger player, the guy who can't miss a long putt, is Donald Wright (who birdied three of the final five holes against Team UltimateBet). A lanky, mini-tour golf pro from Georgia, he takes an awfully long time to set up for every shot, but then mitigates the maddening process by seeming to do the impossible on the course. "I hooked up with Michael through a golfing friend," says Wright, after rolling home a string of miraculous putts to win round two of the Big Stakes event and insure that Jordan will recoup his $100,000 investment (all 16 teams that make it to day three get paid 100K). "Michael played a couple holes with me and decided I'd be the guy to go with."

Good choice until Wright and his teammate, Dave Schreyer, go up against California's John Wilson and Washington state's Mark Worthington, who manage to snag the third-round match on the final hole. But Wright shrugs it off. He's happy to have won back Jordan's investment. On the night he gets knocked out, Wright is spotted sliding into a car with a bevy of sexy women from event sponsor Sportsbook.com. They're all heading to Las Vegas, where they will meet with Jordan and attend a boxing match. For a guy who just lost his shot at seven figures, Wright looks pretty darn happy.

Clearly, it's not a bad consolation prize, but nothing like the dream that's being clung to by team sponsors and players who remain in the running for the $3 million. Besides Wilson and Worthington, the contenders who have survived to day five include Rick Hartmann and Mark Mielke, a pair of country club pros from Long Island who raised their $100,000 via a quartet of wealthy backers; Garth Mulroy and David Ping, two second-tier pros from Arizona, who secured funding from NFL stars Stokes and Verba; and former Major League Baseball pitcher Rick Rhoden and Florida-based club pro Jimmy Gilleon, who are being financed by a syndicate of 20 Atlanta-area country club . While the lanky and highly competitive Rhoden, who won more than 150 games during his Major League career, would surely be happy to win the money, it won't have the potential to change his life the way it would for Gilleon.

Until recently, Gilleon had been knocking around pro golf's mini-tour circuit, hoping for a shot with the PGA. When that seemed increasingly unlikely (due to encroaching middle age and an injury that kept him from earning money on the Tour), he took a job at a Florida country club, but always harbored what-could've-been dreams. Now, if he were to win the Big Stakes event, a couple things would happen: his confidence would soar and, more importantly, he'd have the wherewithal to mount another run at the PGA if he wanted to, thanks to his share of nearly $750,000 that he'd rake in from the tournament. After the fourth round of golf, during which he and Rhoden managed to scratch and claw their way to victory (and a cumulative total of $400,000 in prize money), Gilleon's trying to focus on the golf game he needs to play the next day.

Out by the CasaBlanca Hotel pool, Big Stakes is throwing a Mexican dinner (complete with mariachi musicians—other nights featured a Sinatra impersonator and a piano player singing Billy Joel's greatest hits), and Gilleon explains that the stakes are particularly gargantuan for him. "It meant leaving something behind to give up on the Tour," its the bearded, compactly built Gilleon. "When you play golf for a living, you're chasing a dream. I enjoyed it, but I lost sight of what I was trying to do. It went from going after a dream to trying to make a living. I think about it now and realize that going back out there would be tough." Then, chain-smoking like crazy, he gives the possibility a moment of thought, flashing perhaps on what his share of the $3 million would mean. He ominously adds, "But stranger things have been known to happen."

He has one more round of golf to win to put himself in the final. Lose it, and he will walk away with his share of $300,000 (after the investing syndicate has been paid back its $100,000 off the top). More than chump change, but probably not the kind of money that could put him back on the second-tier pro circuit, where the costs are high and the revenue low. But he's a real contender for the grand prize. Beyond Gilleon's own game, one element in his favor is the presence of Rhoden, who's won 49 out of the 150 celebrity golf tournaments he's competed in. As one knowledgeable spectator puts it, when asked to handicap the remaining twosomes, "I like Rhoden and Jimmy. Jimmy can obviously golf, and Rhoden, well, he knows how to win stuff."

In a tournament that has attracted a smattering of retired professional athletes—former NFL quarterback Billy Joe Tolliver among them—Rhoden is the single remaining ex-pro. He carries himself with a stolid, nonemotional demeanor, sucking it up when he misses the green and advising Gilleon to do the same, so as not to give the competition anything to feel good about. This advice comes in handy on the fifth (and penultimate) day, when Gilleon and Rhoden are playing a do-or-die match against Garth Mulroy and David Ping, the two twenty-something pros from Arizona.

By the eighth hole Rhoden and Gilleon are behind by three, and Rhoden is doing all that he can to keep from ramming a golf club into the ground. Considering that Gilleon previously commented on how every Big Stakes match has been a war for him and his partner, it is no surprise that this one, which pits them against the wunderkinds of the tournament, promises to be a battle royal. For several years Ping and Mulroy struggled on the mini-tour circuit, but here in Mesquite, they appear to have come into their own.

Two days earlier, during the third round, South African Mulroy shot his first-ever hole in one. He complemented it with two eagles and six birdies, establishing himself as the most dangerous man in Mesquite. His performances go a long way toward explaining why the dynamic duo has barely lost a single hole and has kept the pressure on its opponents. It's displayed after Gilleon sinks a five-foot putt to win the ninth hole and the Ping/Mulroy team bounces right back to snag the tenth. After the 15th hole, Ping and Mulroy are ahead by four, guaranteeing them the victory and a spot in the final. However, despite what seems like an easy win (Ping and Mulroy combined to shoot 12 under par on the first 15), Ping stunningly (almost cockily) acknowledges, "This has been our worst round of golf all week. But we hammed-and-egged it and managed to get through."

With the much-ballyhooed richest 18 holes in history on the line tomorrow, these young guys with the NFL stars backing them know that they'll be in for a fight. And they seem to fear that their momentum might have been cruelly drained at the worst possible moment. "We've got a bit of work to do today on the driving range," says Mulroy. "If we play tomorrow the way we did today, forget about it."

Meanwhile, still hanging around the 15th green, a victorious Ping hugs his wife, Karen, and says, with no small amount of relief in his voice, "We'll be able to pay off the credit cards"—and then some, as he and Mulroy ham-and-egg their way to a gross payday of at least $675,000. Ping turns away from his wife and says, "I guarantee you, Garth and I have more debt than anyone else around here. We're not making the checks we want [on the golf tours] and endlessly throw out the green to keep playing. Last year, I made $16,000 from golf but had $60,000 in expenses."

While the winners celebrate, Gilleon stands stiffly alongside his golf cart. He stares straight ahead and purses his lips tightly. A couple of reporters press in on him. "It was a good time, a good tournament," he softly says, doing his best to hide his disappointment at not only losing a shot at the championship, but potentially losing a shot at his dream. "I want to do it again next year."

One of the reporters wonders what Gilleon learned about himself through this experience. "Not much," he says, barely moving his lips, choking on the words, seemingly holding back tears. "It just didn't work out the way I hoped it would."

Illustrating the Darwinian brutality of single elimination, the Gilleon/Rhoden team disappears into the tally books while victors Ping and Mulroy eventually make their way to a corner of the Big Stakes media and players tent (located adjacent to the course's clubhouse). Sitting around with a posse of friends and relatives, they sip from cans of Bud, soak in the adulation and psych themselves up for their big day tomorrow.

In an opposite corner sit their $3 million opponents: Hartmann and Mielke, the pair of country club pros from Long Island. Both men are in their 40s and are veterans of various U.S. and British Opens (which, they say, were a lot more nerve-racking than this tournament). Hartmann, who put together the team and raised most of the financing from three of Atlantic Country Club's well-heeled , explains, "I've been a pro there for 12 years; the care about me and my wife. This money will not change our backers one way or the other—but my first priority here was to win back their initial outlay. Now, however, we're in a position to do a lot more than that. And people at the club are celebrating, following results on the Internet."

A fourth backer, Andrew Rosen, who's a friend of Hartmann's and the wealthy proprietor of the Manhattan-based Theory fashion house, plans to fly in for the final and watch his guys take a shot at the $3 million. Mulroy and Ping (the son of a sports agent named Doc Ping, who happens to represents Stokes) have brought in their families as well as the two NFL stars who backed them. Less than 24 hours before the golfers will make history by teeing off for the mammoth purse, I can't help but what Jeff Friedman told me before the tournament. He said that a major X factor would be how players handle the inevitable pressure of golfing for what will surely be the biggest payday of their lives—his point being that any one of them could focus too intently on the cash at stake and choke.

Now, with the $3 million so clearly in sight, I wonder how Hartmann and Mielke, who is the pro at Mill River Country Club, are keeping those wads of hundreds from clouding their thoughts. "You try not to think about the money, but it's there; and it's impossible to avoid," says Hartmann. "For Mark and I, that money will pay off our mortgages. I'm not planning to go pro again—I hate traveling—but think of how nice it would be to have your house and all your other bills out of the way." In other words, the money's too important to ignore, but it's critical that they do everything in their power to keep it from affecting their decisions on the course.

One day later, by the sixth tee box (which inaugurates an uphill par-5 hole), Hartmann and Mielke have taken baby steps toward winning the whole thing. Following Hartmann's clutch putt on the sand-trap-intensive five, he and his partner are leading by two. But the playing conditions have suddenly worsened. Slate-colored storm clouds hang low in the sky and dry desert winds whip across the course, kicking up dust and making it increasingly difficult to chip with precision.

The windy conditions seem likeliest to hurt Ping, who must pitch out of a sand bunker on the sixth hole. Much to everyone's shock—including his own—he does it brilliantly, getting to within 10 feet of the hole before cutting loose with a stuttery little putt that circles the cup and seems poised to go around it before dropping in. It puts the young guys to within a hole of their competitors, and they tie the score on the par-4 seventh, after Mulroy's second shot hits the pin and lands just a few feet from its destination.

By the time they get to the 16th hole, Ping and Mulroy have taken a two-shot lead. They've placed the pros from Long Island in practically a must-win situation. A series of bad rolls, augmented by wind-related difficulties, leave the two teams tying, thus turning the 17th into a do-or-die situation for Hartmann and Mielke. The gallery of spectators has grown to 100 or so strong, ranging from family to disinterested locals to media to investors. Andrew Rosen, who heads up the group backing Hartmann and Mielke, looks dapper in a Prada ensemble of shorts, sneakers and T-shirt. He is into the competition but seems more proud than concerned. The football pros (who backed Ping/Mulroy), accompanied by their pretty blonde girlfriends, are already in party mode, delighted that their investment has cinched a six-figure return. And the golfers themselves are so plugged in to the task at hand that they hit their very best tee shots, which all land near one another in the center of the fairway.

From behind the green, spectators spot a ball arcing up and landing within feet of the pin. It could be a tournament-clinching shot. Just one problem: nobody up here knows who hit it. When word comes that it was either Ping or Mulroy, their contingent of fans explodes with applause. Verba and Stokes joyously beat on each other, as if it's the lead-up to a Super Bowl, and Mamas Ping and Mulroy are practically in tears. Meanwhile, Andrew Rosen runs a hand through his bristly salt-and-pepper hair, smiles curiously, and assumes a wait-and-see attitude. Turns out that it was actually Hartmann's shot. Whoops. He and his partner take the hole, leaving themselves with the very real opportunity of tying the event on the 18th and bringing it into sudden death.

Like just about every match of the tournament, this final one is settled on the greens. Miraculous shots from the fairway and sand notwithstanding, the difference between winning and losing invariably comes down to putting and strategizing. It is fitting, then, that the potential to win $3 million ultimately rests on Mielke nailing a medium-length putt for a birdie, which will possibly force a 19th hole. He sets up, connects with the ball and sends it beelining for the cup. Spectators hold their breath, as the ball dips a little to the left but still seems likely to drop in. It kisses the edge of the hole, rolls around, and stops a few inches from its target.

Ping and Mulroy immediately jump into each other's arms. The $3 million is theirs (each will walk away with $975,000 once the sponsors are paid off). Their NFL backers do end-zone dances on the green. Ping insists that the winning sum is so huge he can't even relate to it. Good-sport kudos are offered by Hartmann and Mielke, as their backer gives them bear hugs and tells them they did a great job. "We did better than most of your race horses," Hartmann tells Rosen with a laugh, not seeming too sad about his share of the $675,000 consolation prize.

Stepping toward the outskirts of Big Stakes' post-game action, Andrew Rosen looks pretty pleased as well. ing that Hartmann and Mielke flew out on Jet Blue with bargain-basement tickets, I can't help but wonder if they're going to fly home first-class on a tonier airline. "We're heading back on my jet," says Rosen. "Play a round of golf for $3 million, and you deserve to fly home on a private plane." v

Michael Kaplan is Cigar Aficionado's gambling columnist.