Thomas "Hollywood" Henderson Won Lottery After Retiring From NFL

Published on July 15th, 2024 9:55 pm EST
Written By: Dave Manuel


Thomas "Hollywood" Henderson is certainly one of the most interesting characters to have ever played in the NFL.

After missing his junior year of high school football due to an eligibility issue (he moved to Oklahoma City to live with his grandmother), Henderson wasn't recruited by any colleges in his senior year.

Henderson decided to walk onto the Langston University football team, where he would win various accolades, including being named a small-college All-American defensive end twice.

Henderson, who was also a track star, garnered enough attention to be taken by the Dallas Cowboys in the first round of the 1975 NFL Draft.

Henderson earned himself the starting strongside linebacker job in the 1977 season, and ended up being named to the Pro Bowl in 1978. Henderson was also a part of the Cowboys team that won the Super Bowl at Super Bowl XII.

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Henderson, however, had some demons that would ultimately cost him his career.

Henderson was addicted to drugs and alcohol, and would snort liquid cocaine during games that he kept hidden inside of an inhaler. After an incident in which Henderson mugged for the cameras during a Cowboys loss, head coach Tom Landry decided that Henderson was done with the Cowboys.

Henderson would admit that he had a drug problem in 1981, and was one of the first high-profile players to enter a drug rehab program.

After bouncing from the 49ers to the Oilers to the Dolphins, Henderson suffered a neck injury that would end his career.

Henderson would be arrested in 1983 and serve nearly 2 1/2 years in jail for a variety of charges.

Henderson had hit rock bottom.

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After leaving jail, Henderson turned his life around.

Henderson was happy with his life, but things would improve dramatically when he won the lottery in 2000 for $28 million.

Henderson, after squandering his NFL career due to a drug addiction, was now suddenly flush with cash.

The previous version of "Hollywood" Henderson would have blown through this money, though Henderson was now a changed man with kids and grandkids.

Henderson would start a charity and donate a significant amount of his money to various causes.