Billy Walters’s life reads like it could have been dreamed up by Mark Twain. He was born in 1946 with a plastic spoon in his mouth, in the backwaters of Kentucky. Walters’s father, an auto mechanic, died when Billy was eighteen months old, and shortly thereafter his mom ran out on little Billy and his two siblings. His grandmother took Billy in. She preached that hard work was the ticket to a better life, and he brought an almost evangelical fervor to his jobs, beginning at age seven, when he secured a $40 bank loan—arranged by grandma—to buy a power lawn mower. Two years later, he borrowed another $90 to start a paper route. When he was fifteen, his grandmother died and Walters moved to Louisville to live with his mom and her new husband, who made him pay rent. He worked at a bakery in the morning and a gas station at night. Walters eventually became a used-car salesman in Louisville, papering the town with self-promotional leaflets and relentlessly cold-calling customers. In 1966, at the age of twenty, he cleared $56,000, equal to half a million dollars in today’s money. Six years later, he founded Taylor Boulevard Auto Sales, selling wholesale cars throughout the Southeast. That was the seed of a business empire that would grow to include numerous car dealerships, commercial properties, and rental-car franchises.
Walters made his first bet when he was nine, wagering $125 of his paper route money, that the Yankees would beat the Dodgers in the 1955 World Series. That didn’t work out so well, but he kept gambling and eventually began working as a bookie. “I probably came in as a gambler and I am going to go out as a gambler,” he says. Indeed, in his twenties he lost his house playing cards. By 1981, Walters had left the car business and become a full-time sports bettor, running his own book. After run-ins with the law in Kentucky, he moved to Las Vegas in ’82. Pit bosses soon learned to recoil at the sight of Walters. During one thirty-eight-hour binge at the Golden Nugget in Atlantic City, Walters won $3.8 million playing roulette. (Having observed a wheel bias, he bet 7-10-20-27-36 over and over.) Walters also won the 1986 Super Bowl of Poker, good for a $175,000 payout.
Walters’s big breakthrough in the early 1980s was to employ computer analysis in sports betting. He partnered with an exciting venture that had a purposefully bland name: Computer Group. They began betting millions of dollars every week, and Walters would woof that over the next four decades he had only one losing year, with annual winnings often running into the mid-eight figures. Naturally, this drew scrutiny from law enforcement. The FBI raided the headquarters of the Computer Group in 1985, and Walters and his associates were charged with illegal interstate gambling. They beat the rap. In ensuing years, the state of Nevada indicted Walters for similar crimes on three separate occasions, but he was never convicted, turning him into a cult figure around Las Vegas.
One other thing about Walters: he loves golf and is always on the lookout for a pigeon.
How do you replicate the adrenaline rush of hitting a 6-iron off pine straw through a forest over a creek to win the Masters? You can’t, really, but Phil Mickelson has always tried to get his fix through gambling. “He loves the action,” says his old friend Rob Mangini. “There have been many times when Steve Loy said he could get him $500K for a corporate outing, but Phil turned it down, saying he wanted to be with his family. But if I called him up that same day and said, ‘Hey, there’s a guy at Whisper Rock who wants to play you for ten thousand dollars,’ he would jump in his jet and fly over here, even though he was spending twenty-six thousand dollars or whatever on fuel. It’s not about the money for him, it’s always about the action.”
Mickelson’s persona on the PGA Tour is well-honed stagecraft, but what is he like in these private money games? Mark Baldwin, a well-traveled pro who has enjoyed a couple cups of coffee on Tour, got a firsthand look in the fall of 2014, after returning home from European Tour Q School. Baldwin was living in Las Vegas, where there is always action available to a pro golfer who wants to play against deep-pocketed duffers with questionable handicaps. Baldwin had a regular game versus a jewelry salesman and compulsive gambler with a vanity index of 8. Let’s call him Tony. “He reminds me of Joe Pesci’s character in Goodfellas, leaving aside the murderous tendencies,” says Baldwin. “Short of stature with a hyper-caffeinated personality, a quick laugh, and he had likely conquered some disreputable hangouts.” Tony knew a guy who knew a guy who played with Phil, and after some loose talk a game came together; Mickelson wanted to sharpen up before an upcoming Tour event and he had put the word out that he wanted to play against another pro. Knowing the stakes would be too rich for a mini tour grinder just barely getting by, Tony agreed to back Baldwin. Along with another gent we’ll call Matty—a short hitter but clutch putter with an index of 3—they flew out to San Diego on the appointed day. They were driving to the golf course when Mickelson’s partner for the round, a high-powered attorney, called to say the greens had just been punched and they were relocating the game to a different high-end private club in the area. “That felt like a cheap shot, like they were just messing with us,” says Baldwin. Because of the change of venue and morning commute traffic, they arrived late. Mickelson was on the range, drinking a tall cup of Starbucks, and had clearly been working through a big pyramid of balls. Baldwin had made exactly two swings when Mickelson said they needed to tee off right now to get ahead of a big group on the tee sheet. More gamesmanship. Tony is a big personality and a loud talker and Mickelson admonished him on the first tee for being indiscreet in reciting the stakes of the match. “I don’t think he’d ever been talked to like that in his life,” says Baldwin. “But Phil clearly didn’t want the folks at the club to know the size of the game.” Despite the lack of warm-up, Baldwin, then thirty-one, smoked a good drive on number one. As they were walking off the tee, Mickelson said to Baldwin, “I hear you just came back from European Senior Tour qualifying.” The young pro was dumbfounded; the Senior Tour is for players fifty and over. “It was a really weird opening piece of trash talk,” says Baldwin. He replied that unless they had changed the rules to allow guys in their early thirties to play the Senior Tour, he was not yet eligible. “Phil paused for a second, nodded, and just kept walking,” says Baldwin. “He totally meant to say that.”
The betting games were ornate: Baldwin-Tony and Baldwin-Matty versus Phil and his guy and an individual match, pro against pro. Recognizing that he had home field advantage and a slightly longer résumé, Mickelson offered Baldwin either one shot per side or no shots but he could play from one tee box up. Baldwin took the shots mostly so he could club himself against Mickelson from the same tees on a course he’d never seen before. There was no blood on the first three holes and Mickelson continued to big-time Baldwin as they arrived on the tee of number four, an uphill, drivable par-4: “Phil says, ‘Hey, man, this is my course, I’m gonna hit driver, because that’s the way I play. But that’s not the way you should play it. You should lay up with a 4- or 5-iron.’ ” Mickelson hit a pretty good drive toward the green and strutted away, even though Baldwin couldn’t quite tell where the ball landed because of the hill. Without hesitating, Baldwin grabbed his driver and ripped a towering draw that never left the flagstick. They didn’t find Mickelson’s drive; Baldwin won the hole and his playing partner’s respect. “His whole demeanor changed,” says Baldwin. “Suddenly he was so cool and open and gracious, as if we were best buddies. We talked about all kinds of things, just full stream of consciousness.”
Mickelson, whose game continued to be a little ragged, flipped another switch on the twelfth tee. “Man, am I really three down?” he asked.
Yep.
He fixed Baldwin with a hard look and said, “I promise you will not take a single dollar off me.”
Mickelson proceeded to birdie five of the next six holes, his only par coming after he stiffed an approach shot but the short birdie putt horseshoed out. Along the way he didn’t say another word to Baldwin. Arriving at eighteen, a shortish par-5, Mickelson was all-square in his match versus Baldwin, and an extravagant number of presses and side bets were on the line. Overwhelmed by the moment, each of Baldwin’s partners blew their drives off the planet and were in pocket. Both pros hit good drives down the middle, and Baldwin played first, from 207 yards out, to a front pin. He produced a credible shot but his ball ran out on a firm green, leaving him a downhill forty-footer for eagle. “Oh, man, that’s not good,” Mickelson said. “That’s the fastest putt on the whole golf course. You can’t 2-putt from there.” Says Baldwin, “He starts narrating his shot like he’s Johnny Miller and it’s the final hole of the Open. He was four or five yards in front of me and he says, ‘I was deciding between 6- and 7-iron, but 6 brings into play the part of the green where you just went. Now I’m gonna hit the 7. But I can’t get the 7 there. That’s too far for a 7. I guess I’m gonna have to hit it totally perfect.’ ” Mickelson settled over his ball and took a ferocious swing. “I’ll never forget the sound of the strike,” says Baldwin. “It was like a two-by-four hitting a brick wall. Just absolute purity.” Mickelson’s ball tore through the sky, and even before it reached its apex, he intoned, “Ohhh, I did it.” His ball took one hop, grazed the flagstick, and stopped six inches from the hole. “We looked at each other,” Baldwin says of his partners, “and there was this morbid darkness in the air. We could feel the vise closing on us now.” Baldwin narrowly missed his putt. Game over. He has a pro’s discretion when it comes to revealing stakes, but pressed on how much Phil won, Baldwin says, “Tony bought him [the equivalent of] a nice car that day.”
When it comes to betting on sports other than golf, Mickelson swims in even deeper waters. Tom Candiotti, the former big-league pitcher, was once among a big group of friends Mickelson invited to Las Vegas for the opening day of the NFL season. They woke up early in Scottsdale and flew to Vegas in Mickelson’s plane. A cavernous suite at the Bellagio awaited, outfitted with a breakfast buffet and enough TVs to watch every game simultaneously. Mickelson had prepared a tip sheet with his thoughts on each game. The whole crew walked down to the sports book to place their bets. Says Candiotti, “We were kind of standing around, not sure if we should let Phil go first. Finally he says, ‘You guys go ahead because when I place my bets it might move the line.’ ”
(Let that sink in for a minute.)
The entourage went back upstairs and it was like a frat party on steroids: the fellas were tossing around a football and tackling each other on the plush sofas. “Then the games started and things got serious,” says Candiotti. “Phil swept every morning game. He was up over a million dollars.” Mickelson lost only a game or two in the afternoon, increasing his haul. “We were flying home that night, but it’s Phil’s plane, so we’re not gonna leave until he wants to, obviously,” says Candiotti. “He goes down to play baccarat, and he’s struggling. We practically needed a lasso to get him out of there. He stewed all the way to the airport because he gave a lot back at baccarat. A lot.”
Mickelson’s heavy gambling increasingly brought him into contact with men of ill repute. In the mid-aughts, he began placing bets with a mobbed-up bookie out of Detroit named “Dandy Don” DeSeranno. (Mickelson’s lawyer would later say Phil didn’t know about the bookie’s shady connections, which raises a different set of questions about the way he was tossing money around.) Recognizing that his famous client had no leverage and no muscle, Dandy Don simply refused to pay off Mickelson’s winnings of over half a million dollars. This fleecing stayed a secret for a decade and a half before exploding into a public relations fiasco. (More on that later.) One of Mickelson’s golf buddies at the Madison Club, in Palm Springs, was Bryan Zuriff, who would plead guilty in 2013 to his role in an illegal online gambling enterprise with alleged connections to the Russian Mafia; Zuriff, executive producer of Ray Donovan, paid a $500,000 fine and served six months of home confinement. In March 2010, a gambler named Greg Silveira accepted a wire transfer for $2.75 million. This touched off an investigation by the Internal Revenue Service’s criminal investigation unit into what would come to be described as “an illegal gambling operation which accepted and placed bets on sporting events.” Silveira was ultimately indicted on money-laundering charges. During his trial, the federal government produced evidence that “a well-known sportsman” had wired the $2.75 million to Silveira to cover gambling losses. An initial plea agreement with the U.S. Department of Justice signed in 2015 by Silveira and his attorney, James D. Henderson Sr., contained a reference to the “money laundering of funds from P.M.” ESPN’s Outside the Lines cited two sources alleging it was Mickelson who had transferred the money. (Phil and his lawyers have always refused comment on the matter.) California, where Silveira entered his plea, only prosecutes the recipient of the illegal “wages,” not the person who places the wagers. The unsavory characters in Mickelson’s life may or may not be the reason he tricked out his Ford Expedition with armored doors and bulletproof glass. His former PR guy T. R. Reinman offers an alternative explanation, saying “He likes to think of himself as James Bond.”
Could Mickelson afford such staggering gambling losses? Maybe. From 2010 to ’12, Golf Digest estimated his annual income at $41 million; in ’14, it peaked at $52 million. “And Steve Loy was always complaining our numbers were too low,” says Ron Sirak, the writer who put together the magazine’s yearly list of golf’s top earners. A separate question was whether or not Mickelson’s heavy betting constituted a breach of PGA Tour rules. Its player handbook forbids its members to “associate with or have dealings with persons whose activities, including gambling, might reflect adversely upon the integrity of the game of golf.” Tim Finchem was PGA Tour commissioner from 1994 to 2016, and when it came to player misconduct, he instituted Soviet-style secrecy: player fines and suspensions were never to be discussed publicly, to better uphold the image of Tour players as perfect gentlemen. I recently asked Finchem how closely the Tour monitored Mickelson’s gambling. He replied, “We were aware of the basics of what was happening and that’s pretty much all I would say.”
But given the Tour’s rules that prohibit associating with gamblers, shouldn’t Finchem and his army of vice presidents have been watching more closely?
“It’s a close call,” he said. “People could look at it and argue both ways. Under our regulations it’s certainly one thing if you go out and wager during a competition. But then outside of that we don’t pay too much attention to what a player’s doing on his own time. As long as he’s not obviously doing something else that would bring disfavor on the sport.”
But clearly the Silveira trial brought unfavorable coverage to the sport—was Mickelson ever fined or suspended as a result?
“Well, if we did sanction him, we wouldn’t discuss it,” says Finchem.
Okay, so you won’t discuss specifics, but, Mr. Commissioner, can you at least declare publicly if Mickelson was ever fined or suspended as a result of his gambling?
“You can’t have it both ways,” says Finchem, a lawyer who worked as a Capitol Hill lobbyist before coming to the Tour. “You get to ask a question, but you’ve got to accept my answer. Rules of the road.”
That Mickelson and Walters would become golf buddies had the inevitability of a runaway locomotive speeding toward a washed-out bridge. They had first met when they played in the same pairing at the 2006 Crosby Clambake. (Walters won the pro-am portion in ’08 alongside Freddie “Junkman” Jacobson.) They became friendly after running into each other again at the Tour stop in Charlotte in 2008, when Walters played in the Wednesday pro-am. It quickly turned into a mutually beneficial relationship: Phil could pick the brain of a gaming legend, and Billy gained access to the accounts that Mickelson maintained, which was helpful since Walters would regularly get cut off from his own bookmakers because he enjoyed too much success. There is a misconception that Walters was Mickelson’s bookie; in fact, they were partners, regularly pooling their money and splitting the winnings, though Mickelson lost plenty on bets in which Walters did not partake. (Billy once described Phil to a friend as a “rank sucker.”) With Mickelson spending an increasing amount of time at Butch Harmon’s golf school on the outskirts of Las Vegas, the relationship evolved to the point that Phil called Billy a mentor and Walters came to think of Mickelson as a little brother. “There was a real friendship there,” says a close friend of Walters, who has also spent a lot of time around Mickelson; he would speak only on the condition of anonymity. “They’re both larger-than-life characters who have seen and done a lot of things. They enjoyed each other’s company and of course they loved betting against each other, too.” Walters has said he’s faced a putt worth as much as half a million dollars—he drained it—but in his on-course betting with Mickelson, they kept the stakes relatively low because they didn’t want to add any strain to their partnership. According to a sworn statement by Mickelson’s business manager, Phil delivered to Walters in September 2012 a cool $1.95 million to cover losses “related to sports gambling.” These were for the games Mickelson bet but Walters passed on. Phil’s business manager also acknowledged that his client “owed similar debts to Mr. Walters in the past, and had repaid them.” If only there was a way for Mickelson to make some easy money to help cover such losses. Perhaps in the stock market?
Mickelson was unable to build on his 2010 Masters triumph because his body betrayed him. Two months after his emotional embrace with Amy at Augusta, he woke up in Pebble Beach and his limbs wouldn’t work properly. It was the week of the U.S. Open, on a course where he had already won three times, but Mickelson had trouble just getting out of bed due to an attack of psoriatic arthritis. It took months of testing to dial in the right medication. (Naturally, Mickelson wound up as a paid endorser for Enbrel.) The onset of the arthritis occurred within days of his fortieth birthday, and it sent Mickelson down a new path of health and wellness that would ultimately set him up for a decade of age-defying success. But in the short term, he struggled to find his equilibrium, failing to win for the rest of the 2010 season and only once in 2011, while being a nonfactor in the majors.
Still, the holiday season of 2011 brought some joyous news: Mickelson had been elected to the World Golf Hall of Fame. He would be enshrined the ensuing May, during the week of the Players Championship. The ego boost of getting tabbed for the Hall gave Mickelson a little extra swagger at the start of the 2012 season. At the Crosby Clambake, he played well enough through three rounds to earn a spot in the penultimate pairing alongside one Tiger Woods.
On the eve of the final round, Mickelson attended, as he always does, a dinner party thrown by Jim Nantz in the wine cellar at the Sardine Factory, a swank restaurant near Cannery Row. Nantz often seats Mickelson next to Clint Eastwood but, knowing Phil’s affinity for the NFL, on this occasion he was put next to Tony Romo. They hit it off famously. At one point, talk turned to the impending final-round showdown. “Phil says, with great bravado, ‘There is absolutely no way I’m not winning tomorrow,’ ” says Nantz. “Tony is Tiger’s pro-am partner, so he kind of pushes back and Phil says, ‘Have you not been paying attention to the last four or five times we’ve been paired together? I’m in this guy’s head.’ ”
Before the final round, Woods went to the far end of Pebble Beach’s driving range, seeking solitude. Mickelson took his bag of balls and walked clear across the hitting area to set up right next to Woods. Tiger couldn’t ignore him even if he tried, as they were nose to nose, with Lefty facing his right-handed adversary. In the two plus years since Woods ran over the fire hydrant, he had been badly diminished by scandal and injury. He remained winless since the summer of 2009. Now at Pebble Beach, the site of his most dominant victory, Woods had a golden opportunity to reassert himself, and he had clearly been buoyed by his easy chemistry with Romo. The Cowboys quarterback was so worried about upsetting his partner that at the end of the Sardine Factory dinner, Romo beseeched the other guests not to breathe a word to Woods about his new friendship with Mickelson. “If he finds out I’ve been sleeping with the enemy, I’m dead,” Romo told Nantz. But Mickelson is a master of mind games and, walking off the first tee, at the outset of the final round, he shouted at Romo, who was one tee box ahead, “Hey, Tony, what a great night that was last night. I loved being with you, pal. Such a fun dinner.”
Woods shot a glance at Romo, who mumbled something about having had no idea Mickelson was going to be at the meal. Phil half jogged to catch up to Tiger and his partner and continued to lay it on thick as they walked up the fairway: “What a pleasure to get to know you and [your wife] Candice. Thanks for all the great stories….”
Says Nantz, “Tiger was not amused. And poor Tony wanted to run off the course and hide. He was completely shamed.”
Looking like the cat that swallowed the canary, Mickelson birdied the second hole, then the fourth and fifth. After Woods tapped in for a birdie on number six, Mickelson poured in a twenty-footer for eagle on top of him. Just like that he had blown past Woods (and Charlie Wi) to seize the outright lead, and Tiger bogied three straight holes beginning at number seven, appearing ever more mopey with each miscue. He finally showed some signs of life at the twelfth hole, holing a bunker shot for birdie, but Mickelson then stepped up and buried a thirty-footer to save an unlikely par. An even longer putt on fifteen slammed the door. Mickelson shot 64 to roar to victory, trouncing Woods by eleven shots in the worst beatdown of his career. By the end of the round, the once-imperious Woods looked so out of his depth he elicited an unfamiliar emotion: pity. It was the fifth straight time Mickelson had shot a lower score than Woods when they were paired together in the final round, and Phil had now won three of those tournaments compared to zero for Tiger. Mickelson’s fortieth career PGA Tour victory made him just the ninth player in Tour history to reach that whopping number.
After the champion’s press conference broke up, Mickelson casually offered Tod Leonard, a longtime reporter at his hometown San Diego Union-Tribune, a ride south on his jet. “In the awkward five seconds it took me to answer,” says Leonard, “a thousand things went through my head: I’ve got a story to write on deadline…. I have to return a rental car in San Jose…. This is awesome…. Is this journalistically okay?… Will anybody on the plane talk to me besides Amy?” Leonard declined the invitation, which he says left him “shaking.” But to him the moment was revealing of how much the resounding victory over his old nemesis meant to Mickelson. “He was just so out-of-his-mind happy,” says Leonard. “Other than the majors he’s won, I’ve never seen Phil happier.”
In the ensuing two months, Mickelson nearly won at LA and Houston, and he rode that momentum into Augusta. Rounds of 74-68-66 left him in second place, a mere stroke behind European tour fixture Peter Hanson. A fourth green jacket was well within Mickelson’s grasp, a tantalizing prospect as that would tie him with Woods and the great Arnold Palmer for the second-most ever, behind only Big Jack’s six. But on the tough par-3 fourth hole, Mickelson suffered maybe the worst break of his career. With the pin in a perilous position front-left, his preferred miss off the tee was left of the green, which would leave an uphill chip. Alas, he pushed his tee shot a bit too much. Mickelson was unbothered as his ball drifted toward the grandstand left of the green; a free drop would leave him a good angle to save his par. But instead of settling in a fan’s lap, Mickelson’s ball clanged off a metal railing and shot dead left into a bamboo thicket lining the edge of the Augusta National property. He had no room for a backswing but couldn’t take an unplayable penalty because the only place to drop no nearer the hole was deeper into the shrubbery. Mickelson could have swallowed the stroke and distance penalty and returned to the tee box, but for his third stroke he would be replaying one of the toughest shots on the course and he’d have to work hard to make a double bogey from there. So, he took the calculated risk of trying to gouge his ball out of the hedge… right-handed. His first attempt moved the ball about six inches. The next right-handed swing advanced it a dozen steps forward, onto trampled turf where the gallery had been standing, which was muddy after days of rain. Mickelson dumped the ensuing shot into the bunker. When the hole had mercifully ended, he took a triple bogey, tumbling down the leaderboard. Mickelson birdied the three ensuing par-5s to stay in the fight, but ultimately finished two shots out of the Bubba Watson–Louis Oosthuizen playoff. Hanson offered a succinct summary of the bad bounce Mickelson suffered on the fourth hole: “He got buggered.”
Yet a few weeks later, Mickelson lit up the Hall of Fame induction ceremonies for a glittering class that included Dan Jenkins, the Sports Illustrated scribe who invented modern golf writing; Sandy Lyle, the onetime world number one who won a Masters and Open Championship; and Hollis Stacy, winner of the three U.S. Women’s Opens. Mickelson commanded the stage as he told a series of amusing stories that showcased what he called “my own little sick sense of humor.” His voice cracked slightly a couple of times as he offered heartfelt words to his loved ones and reflected on his journey. “I would just like to say that since I was a kid and first picked up a golf club I have been living my dream,” Mickelson said. He added, “I want to thank the fans because they have made this such a fun ride. There have been a lot of highs and lows that we’ve shared together. There have been a lot of times I’ve struggled and it’s been their energy that pulled me through. I’ve tried to reciprocate by launching drive after drive in their general direction.”
It was a good line. Mickelson had no way of knowing that the highs were about to get much higher, and the lows a heckuva lot lower.