What are the odds of winning the Texas lottery? Okay, that’s easy: sixteen million to one, in the fifty-number game. But what are the odds of winning it if your name is Thomas “Hollywood” Henderson? That’s a question of near metaphysical proportions. Depositing a $10.7 million lottery check last March was merely the most recent example of Henderson’s talent for the spectacular comeback, the latest chapter of which began in 1990, when the onetime Dallas Cowboys linebacker returned to Austin’s east side.His football career in ruin but his drug addiction apparently in check, he had come home to give some payback and to get some. First, he got a lease on a long abandoned high school football field where his own sports legend had begun. The lease was provisional, based on Henderson’s ability to restore the facility, a feat that seemed unlikely at the time. Fast-talking, cajoling, and breaking every procedure in the city’s codebook, Henderson managed by 1994 to transform this asphalt jungle into a premier playing field, complete with lights and a scoreboard. Three years later Henderson decided East Austin needed a track facility, and he staged a hunger strike to raise the required $250,000. If Gandhi could do it, Hollywood reasoned, so could he.
With only a tent, a sleeping bag, some water, cayenne pepper, maple syrup, and lemon juice, Hollywood set up camp among the pimps, crack heads, and broken sidewalks near East Twelfth Street. Austinites who had never ventured east of Interstate 35 were drawn irresistibly. “One woman brought her grandchildren, these two little white girls who were running and playing with no idea that they might get mugged or propositioned or worse,” recalls Henderson, who at age 47 is considerably more portly and weathered than the lithe and handsome athlete who once galloped the playing field. “I’m watching her watching them. Then she walks over and puts a thousand-dollar check in my jug.”
For some African Americans, Henderson’s greatest gift to his old neighborhood isn’t the football field, the track, or his charitable organization, East Side Youth Services and Street Outreach. It was his assistance in getting rid of Willie Lewis, a controversial black city councilman who was opposed by East Side activists, shortly after he won the lottery. Though Henderson’s felony record during his drug-using years prohibited him from seeking the office himself, as he initially tried to do, he spent $25,000 in support of the eventual winner, Austin police officer Danny Thomas, another African American. Henderson’s benevolence was not just a political act; it was also a payback for an old affront. In 1984, while Henderson was serving a 56-month sentence in a California prison for sexual assault charges involving trading cocaine in exchange for sex with two teenage girls, the Internal Revenue Service seized his mother’s house (which was in his name) and sold it at a sealed-bid auction. “I got some wealthy friends in Dallas to try to buy it back, but the buyer wouldn’t sell and my mama got evicted,” Henderson told me. “Now, as Paul Harvey says, let me tell you the rest of the story. The buyer’s name was Willie Lewis.” Lewis tells a slightly different version—that Henderson offered to buy the house for considerably less than Lewis thought it was worth, an offer Lewis took as a joke. The house on Sara Drive became Lewis’ headquarters during one of the bitterest campaigns in recent local politics. In a paid advertisement in the Austin American-Statesman, Henderson labeled Lewis’ voting record “poor and divisive,” while touting his own contribution to the commonweal. Lewis told the Austin American-Statesman that Hollywood’s $25,000 might better be used to compensate “the teenagers he molested in California.”This isn’t the first time Hollywood Henderson has reinvented himself. A self-described hustler who can “talk a cat off a fish truck,” Henderson specializes in fighting back against long odds that were his own doing; winning the lottery jackpot seems almost predestined. Deserted at birth by his father, he was raised by his single mother and later a stepfather. The word “illegitimate” on his birth certificate was a source of lasting shame, as was his home environment, where drinking and fighting were common. In 1969, after his sophomore year at old Anderson High, he moved to Oklahoma City to live with his grandmother. “I was sick of sleeping in the same bedroom with my brothers and sisters, seven people in two rooms,” he says, “Sick of going to school every morning smelling of urine.” An extraordinarily talented athlete, Henderson became an all-city defensive end on his high school team. Nevertheless, college recruiters ignored him. “I even wrote a letter to Wichita State, who had lost its whole team [actually, fourteen players] in a plane crash in 1970,” he recalls, “and they flat turned me down. Imagine how that made me feel.”
The year that he finished high school, 1971, was a particularly traumatic one for black males: Henderson estimates that 60 percent of the males from the previous class were already serving in Vietnam. He decided to join the Air Force but backed out just before he was to be sworn in. Instead, he enrolled at tiny Langston University, in Oklahoma City. Playing far above his competition, he eventually attracted the attention of the National Football League. Gil Brandt, the Cowboys chief scout at the time, thought Henderson was among the best players in the country and persuaded Tom Landry to make him the eighteenth pick in the first round of the 1975 draft.
Overnight, Henderson was a personality. His feelings of shame, guilt, and inferiority were sublimated, and his Hollywood alter ego permitted to flower. One of the first things Henderson did was track down the father he had never met. He found his old man in New York and simultaneously discovered grandparents and ten brothers and sisters he didn’t know existed. “For twenty-one years I wasn’t on his radar screen, but now I was somebody,” says Hollywood, who loves to play to his enigmatic side. “Here’s a riddle for you. Thomas Henderson is the oldest of fifteen children but he’s an only child.”
Henderson remembers himself as one of the great linebackers of all time, an evaluation not widely shared. But he was damned good, and he helped the Cowboys to three Super Bowls. One of my indelible memories is of Henderson on a tricky reverse play, returning the opening kickoff against the Steelers in Super Bowl X. Hollywood was the captain of special teams for that game and remembers standing in the middle of the field during the coin toss, thinking, “Here I am, this dysfunctional black bastard in the biggest game in the world, and if they really knew me, they’d throw me out of here.” That same year, Hollywood had his first snort of cocaine. “It made everything okay,” he remembers. “It filled a hole in me, made me feel taller, more handsome, made it okay not to have ties with my DNA donor’s family.” He played Super Bowl XIII with an inhaler of liquefied cocaine inside a pocket of his uniform. By age 26 Henderson had made more than a million dollars and blown it all on drugs, whiskey, and women. Landry fired him just before the Thanksgiving Day game in 1979. “Landry had given me plenty of warning,” Henderson admits. “I was a disruptive influence, disrespectful of the coaches, caught up in my own agenda. Still, I was surprised that he fired me before the thirteenth game of the season. In spite of myself I was a serious contributor to that team. Landry did the right thing, but he paid a huge price. He never took a team to the Super Bowl again.”
The San Francisco 49ers gave Henderson a try. So did the Houston Oilers. So did the Miami Dolphins. By 1981, at age 28, Henderson was washed up, unemployed, addicted, and broke. In November 1983 he was arrested on sexual assault charges. Four days later he was admitted to a drug abuse clinic in Orange County, California. By the time he was transferred to prison, eight months later, Henderson was clean, and he has remained clean ever since. “The fact is, I got rescued from myself,” he told me. “I changed socially and psychologically during those twenty-eight months.” In 1993, when he observed his tenth year of sobriety, his old coach and critic Tom Landry was among those who showed up to congratulate him.
In the grand tradition of hustling, Hollywood has capitalized on his addiction, charging $7,500 for his foundation per appearance for motivational speeches and selling tapes and videos. After his lottery windfall, he doubled his appearance fee to $15,000, calculating that his story is now twice as good. Henderson has long had this cosmic understanding that someday he would win the lottery. For thirteen years, starting in 1987, when he was released from prison, he spent $200 to $500 a week on lottery tickets, always including one ticket with the same six numbers: 17-21-27-10-31-35, the scores of his three Super Bowls. He was so certain he would win that he made lists of things to do and people to remember when his ship came in. (His winning numbers were selected randomly by a computer: Only the 17 and the 35 matched his Super Bowl numbers.) Henderson has given away about $1 million, he says, and transferred still more money to his HHH 56 Investments firm—56 was his football number and the H’s are for Hollywood and his two daughters, 21-year-old Thomesa Holly and 6-year-old Dalis Henderson.
Some people regard the windfall as the ultimate test of Henderson’s recovery. His history suggests that he is never more at risk than when something good unexpectedly happens to him. Hollywood dismisses the notion, however. “I’ve done drugs and drink, done them seriously,” he says. “Those things are no longer an option; they’re a death sentence. I’m the most prepared man on the planet to handle success.”