The Best American Crime Writing 2006

Paige Williams : How to Lose $100,000,000

from GQ

On Christmas Day 2002, Jack Whittaker, a fifty-five-year-old contractor from Scott Depot, West Virginia, won $314,900,000 off a $1 Powerball ticket and became the biggest lottery winner of all time. Lucky Jack.

But for certain guys, winning the lottery can be just about the worst thing to ever happen. You might as well hand them a grenade. Plenty of winners have blown their dough in the post-payoff delirium, but no one has done it quite like Big Jack. One minute he was a good Christian husband, father, grandfather, and businessman, just another respectable old dude in a cowboy hat living his West Virginia life, and the next he was sitting on a curb outside a titty bar, complaining to the cops that an ex-stripper named Misty and her boyfriend drugged his cocktail, busted out the window of his truck, and made off with a half-million of his dollars. And things were only starting to get ugly.

At its best, W est Virginia is as green as Jack Whittaker's millions, but in March it is muddy-river brown. Windowless factories line the Kanawha River, and in between stand forgettable little towns, drab mountain pockets of overworked humanity, connected by interstates. Every other restaurant is a Biscuit World. Fog hangs on the river and on the bare branches of trees. Rain falls on tobacco barns, boatyards, and coal trains, and on the lonely gold dome of the capitol. It's hard not to wonder how this affects a fellow's psychology. A man might be driven to do just about anything in the brown months of West Virginia.

Jack lives now, as he did then, in one of these little interstate towns, called Scott Depot. His house is a two-story brick number, like countless others in these parts. He owns a construction business, Diversified Enterprise Inc., which builds water and sewer systems across the state. He's been working since age fourteen and has been with his wife, Jewell, about that long, too. Supposedly, his company was grossing more than $17 million for a while but ran into some problems, and Jack had to lay off twenty-five of his 117 employees. His adult daughter, Ginger McMahan, has been battling lymphoma. Jack's own health isn't tip-top, either. He loves his teenage granddaughter, Brandi, so much, he named his office building after her: the Brandi Building. Millionaire or not, Jack liked to play the lottery.

Right before Christmas 2002, the Powerball prize climbed to record size. People in twenty-three states, the District of Columbia, and the U.S.Virgin Islands fattened the pot in anticipation of the televised drawing Christmas night. On the morning of December 23, Jack stopped by C &L Super Serve in the town of Hurricane, where Brenda Higginbotham cooked the food that sat under the heat lamp. Like most mornings, she fixed Jack a bacon-and-tomato biscuit to go, pulling out the biscuit guts to help him with his cholesterol. She called him her "cowboy man" and knew him about as well as you can know anyone who stays long enough to order breakfast and comment on the weather. That morning, along with the biscuit, Jack bought $100 worth of lottery tickets.

By Christmas Eve, the pot reached beyond $280 million, and by Christmas Day, $314.9 million.The odds of winning were 120 million to l.When the winning numbers were announced, Jack had all but one. He went to bed Christmas night thinking he'd won five grand. The next morning he learned that the TV had misre-ported it. He and Jewell checked and checked again-Jack had the sole winning combo: 5-14-16-29-53, Powerball 7.

Jack took the onetime payment of $170 million and walked away with $113 million post-tax. He accepted his easy money before a battery of cameras, dressed in a black outfit and hat, as Jewell, Ginger, and Brandi stood alongside him. The governor handed Jack the big poster-board check and said what a good ambassador Andrew Jackson Whittaker Jr. would make for the state of West Virginia. And for a while, that's what Jack was. Right away, he thanked God for giving him the right numbers. He immediately pledged $17 million to several franchises of the Church of God; then he started giving away millions to various charities. Jack bought people houses and cars and college educations, gave money to old people and poor people and Little Leaguers. He was feted and filmed and generally hailed as the pride of West Virginia but "real down-to-earth," which is just about the best thing one West Virginian can say about another.

You could hardly turn on the TV or open a newspaper without seeing Jack in his big black cowboy hat playing the role of Christian do-gooder with down-home brio. He went on Good Morning America and Today and let the perky morning-talk-show hosts slobber over him; then he went back to West Virginia and impressed his friends and neighbors by working the same long hours at the same old job.

He cut checks to the churches as promised. He bought Higginbotham, the biscuit-maker, a three-bedroom home and a used Jeep Grand Cherokee, and did about the same for the clerk who'd sold him the winning ticket. He promised Brandi he'd spend more time with her and do his best to help her fulfill her dream of meeting the rapper Nelly. He set up the Jack Whittaker Foundation and started handing out what his staff says was $60,000 a month in food, clothing, and household items to needy families across the state, which seems implausible until you remember Jack Whittaker won enough money to give away $1 million a year for the next 113 years. He started getting so many letters of need, he had to hire people just to open them. His neighbors had to deal with extra traffic because half the state wanted a look at the home of an honest-to-God dream come true. Jewell told CNN she literally got sick when Jack won the Powerball but has since decided the money is a good thing because of all the people they can help. She has said her greatest desire is to visit Israel so she can see "where Jesus walked," but other than that, all of this just made her want to run and hide. Jack, on the other hand, decided to come out and play.

From a frontage road west of C harleston, near a carpet outlet and the local Bob Evans, the club with the hot-pink awning calls out to the road-weary, marriage-weary, flesh-starved men of Interstate 64. One night Jack Whittaker heeds the call. He strides right into the Pink Pony and throws about $50,000 on the bar. It's New Year's Eve 2002, and he is six days a megamillionaire.

Mike Dunn, the Pony's general manager, runs a smooth establishment and is not the kind of fellow who needs trouble spelled out for him. He takes one look at that wad and decides to have a word with Jack. He goes over, introduces himself to Jack, says, Glad to have you here, sir, but please be a bit more discreet with the dough. He secures Jack a limo and a guard and gets him and his fifty grand home safe and sound. Jack stops throwing around fifty grand but at his subsequent Pony outings still flashes enough cash to make it clear he's a big shot.

It's a summer Monday evening, and Jack has a hankering for vodka and a briefcase full of scratch: $245,000 in $100 bills and three $100,000 cashier checks. He gets rolling at Billy Sunday's, a bar near his office that has a note on the door asking its patrons to please leave their knives and whatnot in the truck. It's a good place to catch a wet-T-shirt contest or a NASCAR race. The staff didn't know Jack before he won the lottery, but they know him plenty now. Sometimes he shoots pool. Sometimes he just sits and drinks his Absolut and orange (or tomato) juice-doubles, if they recall. If he's feeling generous, he might throw down a good tip or give a cute young bartender a gold Rolex pen right out of his pocket, just for the hell of it, because he can, because he's Big Jack. He tells people he's a martial-arts expert and sometimes gets up to do a few karate kicks to prove it.

By the time he gets to the Pink Pony, it's around 2:00 a.m. and he has had, by his own count, seven or eight drinks. He leaves to drive to the Motel 6 to meet a friend, but the friend doesn't show, so Jack drives back to the Pony. He parks his Navigator alongside the front door and locks it with the engine running. The half-million-dollar briefcase is on the front seat.

The kitchen manager, Jeffrey Caplinger, is in charge for the night. Jeff dates Misty Dawn Arnold, an ex-dancer who gave up the pole upon getting pregnant. The other strippers pay her to help them with their scheduling and outfits and hair. According to the club's bartender, the whole thing went down like this: At some point, Misty walks Jack out to the Navigator-maybe he needs more spending money or aims to dazzle Misty with the contents of the briefcase.Whatever it is, Misty comes back inside, says somebody needs to rob that dude.

Jack orders a vodka and tomato juice, but they're out of tomato juice so they make him a vodka and Hawaiian Punch.According to the bartender, Misty dumps a couple of blue capsules in Jack's drink. The bartender says: Misty, what gives? And Misty says: Don't worry about it; Jeff 's outside breaking into the Navigator. Pretty soon Jack can't hold his head up, so they let him lie down in a back room. Toward dawn he staggers outside and discovers one smashed window, zero briefcases. There's a lot of yelling. Jack and Jeff get into it, and pretty soon Jeff 's got a cut on his nose and the Pink Pony is crawling with cops. Jack summons his own security man, who finds the purloined briefcase stashed behind the Dumpster with the money still in it. The bartender later testifies to all of this at a West Virginia Alcohol Beverage Control hearing on whether to pull the Pony's liquor license, a hearing that culminates in an attorney asking Jack if it's common knowledge that he totes around so much cash, to which Jack responds: "You know, I did win the biggest lottery in history."

It doesn't take long for people to start talking about Jack's predilection for loose cash and naked strangers. Christians come out of the cracks to call him a hypocrite, but Jack keeps on being Jack. One November night, at Billy Sunday's, long past last call, they're shepherding stragglers to the door. Among them the management remembers Jack and a woman they know as his girlfriend. Jack seems to get the idea that people are disrespecting her, so on the way out he tells one of the owners, Billy Browning Jr., to knock it off. Browning tells Jack it's simply time to go home. According to Browning and a witness, Jack says something about having Browning killed. Browning tells him not to come back. But a few months later, Jack's back.

Todd Parsons, the manager at Billy's, takes him aside, asks him to leave. " 'You don't want to do this,' " Parsons remembers Jack saying. " 'You don't want to put me out of here. I'll kill you and your family for this. I've got enough money now to where I can have y'all killed and nobody would ever know.' " Parsons, twenty-eight, who has a wife and two young kids, takes this rather personally. He tells Jack he can either go now or talk to the law. Jack swings. Parsons puts him out. The cops come and charge Jack with assault; according to a police report, a security-camera tape backs it all up.

Jack, meanwhile, is still driving the Navigator.A couple of weeks after the Billy's incident, he leaves $100,000 in a bank bag in the Navigator in his driveway, and naturally, someone takes it. The cops are getting sick of telling Jack to put his money in the bank. They've been spending half their time either writing him up or hunting down his loot. Jack installs security cameras overlooking his front porch (bare but for brass planters full of cigarette butts) and over the driveway and garage (silver Rolls, an Escalade, a muscle car missing a wheel or two).

So Jack's starting to become everybody's favorite joke, but while they're laughing they're also crying, because it seems unfair that God or whoever had handed a life-altering sum of money to a guy who not only already had plenty but who leaves it lying around like trash.

Eight days after the $100,000 goes missing, the state police report finding Jack slumped over the wheel on the side of I-64, not far from the Pink Pony. They wake him up and give him some DUI tests. He fails the follow-the-finger, the walk-and-turn, then he blows nearly twice the legal limit on the Breathalyzer. It's 5:30 in the afternoon.

But this snowball's still rolling.Weeks later, someone breaks into Jack's office and swipes $2,000. That same afternoon, Jack gets sued.The plaintiff is Charity Fortner, a young floor attendant at Tri-State Racetrack & Gaming Center, a greyhound track and slots casino down the road from the Pink Pony. Jack is a regular in the High Rollers Room, where the bet limit is $5. Charity's job is to change out the empty coin hoppers. Jack was gambling one day alongside a "lady friend," and when Charity bent to refill the hopper, Jack grabbed her ponytail and shoved her head toward his crotch. So alleges her suit. Fortner declines to comment, but her lawyer, Scott Segal, says, "The fact of the matter is, if someone doesn't take on men who act this way, it becomes acceptable conduct. Will it be an easier verdict to collect [because he's rich]? I hope it will be. But the way the man's behaving, he may lose every last cent before this case is over. He might as well be throwing it in the river."

It didn't take long for Jack to lose some more dough.Two days after the lawsuit is filed, another $85,000 disappears from the Navigator, again from Jack's driveway. The new security cameras record a man and a woman calmly taking the stash before driving off in a van. The cops begin the hunt for a whole new batch of missing money. Jack tells a local TV news crew: "I'm ready to kill somebody."The feeling is now rather mutual."There's been a lot of unfortunate things," says Raymond Peak, the soft-spoken mayor of Hurricane, where Jack scored his lucky ticket. "Carrying around so much money entices people to want to rob him. People think he's nuts. As a public official, it makes it difficult to condone. But it's his money. I guess he can do what he wants."

By now there's no telling how many people are embroiled in the seamier side of Jack Whittaker's good fortune.This fall, a dead guy was found in one ofJack's houses. His body was discovered around the time police were investigating a burglary of the house by two other men, one of whom committed the crime in drag.The dead guy had been a friend of Brandi's, but apparently the Whittakers didn't have anything to do with his death. This is one of the sadder facts of Jack's life now:The trouble he used to invite now sort of lurks in the shrubs. He was even thinking of polling county residents on their opinion of him to see if he could get a fair trial there.

To be sure, a whole tragicomic parade of formerly anonymous people have lined up to testify for or against him in the criminal and civil courts of West Virginia. In addition, several adultentertainment professionals have lost their jobs, and little roadside churches have had to defend themselves for accepting tithes from a guy who's been treating metropolitan Charleston like his private saloon. His own granddaughter has lost friends because she can't decide whom to trust. "She's the most bitter sixteen-year-old I know," Jack told the Associated Press.

At last check, Misty and Jeff and two separate trios of accused thieves were awaiting trial; the cops were still trying to track stolen Whittaker dough; prosecutors were preparing assault and DUI cases against Jack; two more women had sued, alleging that Jack had sexually affronted them between slot pulls; the owners and managers of Billy Sunday's had hired lawyers to defend themselves in a suit Jack Whittaker brought against them; two other, completely different fellows had now sued Jack over another incident at another club (Jack supposedly became enraged over losing a coin toss or something); bartenders dreaded seeing him walk through the door; and Mike Dunn was still trying to get the Pink Pony's liquor license back.

Robby, the Pony's former cook, wound up behind the bar of another gentlemen's establishment, in a mini-mall next door to a boarded-up adult bookstore. He looks a little wistful there one afternoon as he tends the empty club and its trio of strippers, who alternately work their poles and holler at him to turn up the fucking jukebox and to get them another Wild Turkey, goddammit. Robby misses the Pony. He liked his job, liked his boss, and probably would have kept on there if not for Jack's shenanigans. Like most everyone else, Robby doesn't say too much, because nobody cares to bad-mouth a guy with a load of lawyer money. "Besides," Robby says, "in West Virginia, rats get hurt." He did offer this, though: "People think money gives them power. But it don't."

The huge sign over the C &L Super Serve (the big one sold here!) now seems less celebratory than ironic. Even Jack's preacher, whose little Tabernacle of Praise is $7 million richer, doesn't defend Jack so much as pretend he doesn't exist. When asked about the drinking and fighting and strippers, pastor C.T. Mathews said, "I don't know what you're talking about."Then,"What he does is his business. Here, we talk about our business and the Lord's business."

Lots of people around Scott Depot wish Jack had taken his business elsewhere. "I'll tell you what he should have done: He should have taken that money and gotten the hell out of West Virginia," one bartender said."That's what I'd have done. I'd have bought me an island."

Jack's biggest mistake, though, was probably a gross deficit of subtlety. In flashing his cash, it's almost as though he wanted people to take it. Maybe he felt he didn't deserve it. Or maybe the money made him feel invincible, like the badass he always suspected he was-or wasn't. Maybe he was trying to simultaneously redeem and punish himself. Maybe he broke beneath the burden of divine good luck. But here's the thing. Even though he has been arrested, sued, banned from bars, robbed, and ridiculed, is down $155,000 in Navigator losses alone, and stands to lose thousands more in legal fees, Jack Whittaker has another $100 million or so to lose. So if he should decide to go ahead and blow everything, he'll have a hell of a long way to go.

God help West Virginia.

Paige Williams is a nomadic writer who currently lives in New York. Her story "The Accused" appeared in The Best American Crime Writing 2003.

On the surface this seems like a laughable story, the misadventures of a country goofball. I can say country because I'm from Mississippi and I can say goofball because maybe it takes one to know one except that I don't go to titty bars or have half a million dollars to leave around in a truck. I'm drawn to stories, though, of people whose dark need for respect or drink or vengeance or redemption (it's all the same monster) brings out their most interesting demons. Southerners are particularly good at this. We dig our graves with the most colorful shovels.

These are often tragicomic figures worthy of Shakespeare, to be pretentious about it, and while some might consider a story like Jack Whittaker's a cautionary tale I would say no; we learn our own lessons by our own hand and simply note-with pity, awe, compassion, resentment, gratitude, whatever you're made of-the fatal flaws of others. Jack's fatal flaw, I believe, was a need to stand big- to be reckoned with, to be awed. In America but especially still in the rural or uneducated or undereducated American South nothing does this quicker than dollars. Everyone may not understand the rest of the known world, or want to, but a particular band of Southerners relates solidly and with Pavlovian reliability to money. A Ph.D. means nothing, and an MD everything. John Grisham is a literary hero for his zeroes. I could tell my family this story appeared in GQ and they would say,"That's nice." I could tell them GQ paid me $25,000 for it (which they certainly did not) and my family would love and celebrate me forever. A price tag legiti-mizes-or illegitimates-everything.

I wish I could say everything worked out for Jack Whittaker but I'm not sure that will ever be true. From the time we closed on this piece and the day it hit the racks,Whittaker's life got perhaps predictably worse. An eighteen-year-old friend of his granddaughter Brandi Bragg overdosed at Whittaker's house; the kid's father is suing Whittaker for not having had better "control" over Brandi. (A lot of people thought Whittaker spoiled her. He paid her $109,000 a year to work at his construction company. She was seventeen.) Then,Whittaker was charged with yet another DUI, and with carrying a pistol concealed in his left boot, after his Hummer hit a concrete median off the West Virginia Turnpike. He had $117,000 in cash on him at the time.

Some said winning the Powerball was the worst thing that ever happened to the guy but then the worst thing actually did happen. Brandi was found dead. Her body was discovered the day our issue appeared on newsstands. The timing was sickening. It took months for the details to emerge but basically Brandi and her boyfriend partied one night with cocaine injections and methadone pills and Brandi died in the boyfriend's bed. The boyfriend freaked. He wrapped Brandi in a sheet and a tarp and dragged her out to the yard and left her beneath a junked van. She lay there all through the manhunt, for two long weeks. Finally the boyfriend showed the state police where he'd put her.

They buried Brandi on Christmas Eve, nearly two years to the day Jack Whittaker won big.

As for the Pink Pony debacle, that one apparently has yet to be resolved. In the Billy Sunday's case Whittaker pleaded no contest to misdemeanor assault but later asked the judge if he could take it back and stand trial because he decided the sentence of unsuper-vised probation and weekly AA meetings was too harsh (answer: ah, no).

And on it goes.

Big Jack apparently now lives in Virginia yet has been gilding and gilding the little Tabernacle of Praise, which isn't so little anymore. It's grown from a $4 million church to a $10 million 13.5-acre "campus."

Not long ago he told the Beckley Register-Herald: "I don't have nothing to live for since my granddaughter's dead." But then he said he will use his millions to establish West Virginia rehab centers for teenage girls (Brandi twice went to rehab, out of state). He told the Charleston Gazette: "That's what I'm spending my life doing." I suppose we'll see.