Comeback • Thomas “Hollywood” Henderson

By winning the lottery, the trouble-plagued former linebacker changed his life—again.

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

More Texas Monthly

Loading, please wait...