A Flight to Remember with Thomas “Hollywood” Henderson

I am speaking today at the Oklahoma City Town Hall and have enjoyed returning to this wonderful city. Yet, while this city never ceases to amaze me, it was the flight to Oklahoma that proved overwhelming. Before my flight, an older man called me over at the gate to say hello. It turned out to be Thomas “Hollywood” Henderson, the Super Bowl champion and Pro Bowl  linebacker.  It then turned out that we were not only flying on the same flight but were seated next to each other. What followed was an incredible conversation with the former member of the “Doomsday defense.

It turns out that we are both speaking in OKC on Thursday. However, the subject of Henderson’s speech is particularly poignant.  The only thing more impressive than Henderson’s football career is what occurred after his career. It is a story of redemption from the ashes of utter self-destruction. In the case of Henderson, his demise was played out in front of millions and, for most fans, he vanished from the public eye.

On November 8th, Henderson will have been sober for 39 years after tackling addiction to alcohol and drugs that left him with blackouts and left his career in tatters. He will be speaking at a sobriety center about his struggle and it is a story that everyone should hear.

The flight was filled with stories about playing against football legends, including my hero Walter Payton on the Bears. (He cut me little slack as a Bears fan and noted that he never lost a game to the Bears or Payton ).

Henderson is living NFL history and offered vivid accounts of working with the likes of Roger “Captain America” Staubach and even O.J. Simpson. He was even coached by Mike Ditka during his stint as an assistant head coach with the Cowboys. He also discussed his diagnosis (and settlement) for Chronic Traumatic Encephalopathy (CTE) like many in his generation of NFL players.

Henderson was part of the “Doomsday defense” that was the most feared line of its time. In his carry-on bag were his three Super Bowl rings, including the Cowboys defeating the Broncos in Super Bowl XII in 1978. (I was more freaked about the rings than Hollywood and pushed him to zip up the bag on the way off the flight).

Henderson played against the Steelers in Super Bowl X in 1976. He played again against the Steelers in Super Bowl XII in 1979. All close games that were some of the most exciting in history. He was known for his taunting of the Steelers and Terry Bradshaw (who shared the cover of Newsweek with Bradshaw before the Super Bowl).

Yet, Henderson was struggling with a towering drug addiction to crack and cocaine. We discussed how he fell more and more deeply into addiction while partying with his close friends Richard Pryor and Marvin Gaye.

It would ruin the remainder of his career in a crash-and-burn played out on national television. He even reportedly did drugs before Super Bowl XIII. He reached the bottom when he was charged with sexual assault after snorting cocaine with two teenage girls. Henderson says that he remembers nothing from the incident but he vividly recalls the shame that he felt later in telling his mother of the charge. He pleaded no contest and entered a rehab program. He would be there for months and it changed his life.

He has been clean ever since and now actively works with addicts around the country. His trip to OKC holds particular meaning for him because he graduated from high school in the city. He recounted how he was heading into an all-too-familiar pattern in Austin, Texas where he was born.  He decided to call his grandmother and ask if he could live with her. She said yes and changed his life. He would go on to become a first round draft pick after playing for Langston University and being selected as Southwest Defensive Player of the Year.

As an avid football fan, I was enthralled by the football stories that flowed from Henderson. However, the most inspiring moments came from his account of his struggle against addiction. It was self-effacing and honest, particularly in discussing the deep shame in facing his mother over his conduct. She would live to see him sober and dedicated to helping others who are facing the same struggle.

He is flying high in exactly the way that his mother hoped he would: as a symbol to others that they can recover and rebuild from lives left in self-induced destruction.

Henderson came to the speech despite being less than four weeks out of knee surgery and still in pain when walking. I insisted that he allow me to get him a wheelchair after the flight and, as we waited, asked if he might need a bit more recovery time. He said he had to come. It was not just that it was OKC or that it was part of his commitment to sobriety programs. Knowing my Bears allegiance, he said wryly with a smile, “you just learn that when Payton’s on the field, you got to get in the game.”



40 thoughts on “A Flight to Remember with Thomas “Hollywood” Henderson”

  1. He was only on one SB winning team as a player..Where did he get the other two rings? Was he coaching in the NFL?

    1. David, players on each team…winning and losing…are given a Superbowl Ring.

      Henderson played in three Superbowls (X, XII, and XIII), thus he has three rings.

  2. Thanks for an inspiring insight. One of my closest friends represented Walter Payton and relates some fun stories.

      1. LOL.
        He did win the Texas lottery in the year 2000 ($28 Million Dollars), but he did not give it all to his church.
        He used about 10% of it to start a charity and make two donations to the community where he grew up…and kept the other 90%.

  3. What a great and positive story. There are a few snide comments, but…those of us who have travelled the journey of addiction that Mr. Henderson has (there are literally millions of us), stayed clean and sober and worked to help others is incredibly uplifting. Addiction is an insidious disease – yes, it is a disease. Hollywood Henderson is a fantastic person, giving back to struggling addicts what was freely given to him. God bless HH!

  4. Redskins fan here. Now THAT was a rivalry! Mean men on both sides of the ball. As for Walter Payton? Walter Payton’s last game for the Bears was a playoff game against the Washington Redskins. Knocked him out at half time. Cowboys? Troy Aikman’s las play was against the Redskins when LaVar Arrington ended his career in the second quarter. Boom!

    1. Skins Fan I remember Sweetness sitting on the bench with his helmet on after his last game. I don’t recall him having been knocked out at the half.

      1. I well recall – National Football Conference Semifinal , Washington R – E – D – S – K – I – N – S vs . Chicago Bears at Soldier Field , Sunday , 1 7 January 1 9 8 8 .

        Bears , up 1 4 to 0 ; game tied at fourteen at the half . DARRELL GREEN returns a punt forty – seven yards for the winning touchdown in the third quarter .
        Chicago ‘ s Kevin Butler kicks a field goal to cut the lead , but neither team scores after that .

        Walter Payton , on fourth down and seven , catches a Jim McMahon pass and advances the ball for six yards , ball goes over , Washington wins , 2 1 to 1 7 .
        Payton ‘ s disappointment at losing his final game is arduous , and he sits on the Chicago bench long after the final gun .

        Grateful though I was that the R – E – D – S – K – I – N – S would win Super Bowl X X I I two weeks later , the sight of Walter Payton on the bench , still wearing his
        helmet , inconsolable , is one of the saddest memories have I of pro football .

        Box score , Washington @ Chicago , 1 7 January 1 9 8 8 , https://www.pro-football-reference.com/boxscores/198801100chi.htm .

  5. Now there’s a name I haven’t heard for a long time. What a great guy. Thanks for sharing your story.

  6. Did the Dallas Cowboys hire and promote through an unconstitutional, government-mandated policy of affirmative action?

    Answer: No.

    “Hollywood” Henderson earned three Super Bowl rings the old-fashioned way.

    He EARNED them!

    1. Oh, and Professor Turley is a shameless name dropper.

      No, no.

      I’ll bet “Hollywood” Henderson ran right out and told everybody that he just met America’s Lawyer, Professor Jonathan Turley.

      Question: Who got whose autograph?

      1. You are a simple minded fool. Only a fool who take a story about REDEMPTION and say something as stupid as this… Your comment really makes me worry for humanity.
        Your mama is calling and needs the trash taken out… AGAIN. Get upstairs and get it done. Maybe take a shower while you’re up there. WORM.

        1. Hollywood Henderson changed his life under the encouragement of coach Landry. He was even asked to recite a eulogy at his funeral. Anyone who detracts from his story doesn’t K ow of all his accomplishments!

        2. The intended humor went right over this erudite, scholarly, highbrow and entitled “victim’s” head.

          “A man may well bryng a horse to the water, but he can not make hym drynke without he will.”

          – John Heywood, 1546

      2. I’m weak in some areas, but I know enough about lawyers, if Prof Turley was talking Hollywood or someone is likely getting a bill. LOL;)

  7. As always, another great article for us to chew on. BTW, in 2000 he won 26 million in the Texas Lotto. I seem to recall he won two big time lottery payouts, but i was only able to verify one of them.

    Speaking of Walter Payton, I was fortunate enough to meet his backup running back for the Bears who shared with me the time he came home after playing on Thanksgiving to his suitcases packed by the front door and a cold uncooked turkey on the kitchen counter. He told me Payton had called his wife pretending to be the backup running back’s girl friend, telling his wife how unfair it was that he had to spend Thanksgiving with his wife and not the girl he really loved. He immediately called Payton telling him he better fix things with his wife or he would open his own can of whoop-backside, with some things I will leave on the cutting room floor.

  8. Stories of Redemption are always excellent reading!

    Now if we could just get the Good Professor to join the Republican Party…..that would be another such story I would love to read.

  9. I agree, a great story. Addiction is awful and one of the toughest things to beat. Those that come back from it are truly a gift to us all. It’s like a soul that is lost returns to us.
    Chance meetings during travel like this came be incredible because they are so unplanned and can be more exciting than the original reason for the trip.
    I sat down to breakfast at a bar in a hotel restaurant in Ok City, of all places, because it had no other open place to sit. Soon after 4-5 musicians from Kenny Rogers band (they had performed a concert the previous night) came in and sat on both sides of me at the bar and just started talking and joking and pulled me into their conversation like I was an old friend (I had never met any before). Truly one of the greatest breakfasts I ever had and definitely the most hilarious.
    You just never know.

  10. “He was known for his taunting of the Steelers and Terry Bradshaw (who shared the cover of Newsweek with Bradshaw before the Super Bowl).”
    Super Bowl XIII (1979):
    Steelers 35
    Henderson (and Cowboys) 31

    Terry Bradshaw MVP

    Oh and nice catch Jerry:

  11. I enjoyed the Cowboy team through those years – being a Texan and Cowboy fan since their inception. Henderson was blessed with extraordinary speed and physical skills, and was a constant problem child for Tom Landry and the team. An amazing thing: he was probably the only player that Landry put up with in spite of his self-destructive nature.

  12. Professor, the organizers of your trip couldn’t have done a better job to book you a seat next to Thomas “Hollywood” Henderson, just shy of some months to turn 70!

    Every life have ups and down and especially for those on the spotlight the dirt goes public. For me what “Hollywood” made so special that he don’t whitewash what happened 30 in the one way or the other 30 years ago.

    What also should be mentioned that Thomas won a Texas Lottery Jackpot of $ 28 Million in 2000. He not only founded HHH 56 [1] Investments, Ltd, but also opened “East Side Youth Services & Street Outreach” Charity and has made generous donations to the East Austin community where he grew up. He currently gives motivational speeches and sells videos of his anti-drug seminars.

    Imagine Thomas Henderson, former Speaker of the House and Presidential bider Newt Gingrich met up with Herschel Walker on his campaign trail. All three have some stories to share…

    [1] 56 was his number, later worn by outstanding “linebacker” Lawrence Taylor.

    1. Thanks for the background details, I always wondered what he did with the lottery money. If only more of the winners did something like that. You can web search using terms like “what happened to lottery winners” and an awful lot of the stories wind up tragedies or close.

  13. Henderson’s is a great story. Unless you or a loved one has gone through this struggle, you really have no idea what it is like. One thing I learned is that addiction is a mental illness which must be faced head-on and not hidden to avoid shame.

  14. After he finished his time in treatment, I met him when he arrived at the California Men’s Colony to begin his 2 year prison sentence.
    He was a model inmate, never requesting special treatment but looking for ways he could be of service to others.
    I was convinced that he’d had a genuine wake-up call and was truly humbled as a result.
    I’m really happy to hear that he’s stayed straight and is still helping others. ~ MTA Thomas, D-Quad

  15. A moving tribute. Important to highlight stories of redemption and of people dedicating themselves to helping others. As to Da Bears, it’s a long time since ‘85.

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