[2] Tillman twice defeated Mike Tyson as an amateur, winning both bouts via close decisions.

Tillman turned pro in 1984 as a cruiserweight and had a disappointing professional career, primarily due to a weak chin.

At the 1984 Summer Olympics Henry met his bride-to-be Gina Hemphill, a granddaughter of Jesse Owens, she carried the torch into the Los Angeles Coliseum at the opening ceremony, and worked as a production assistant on The Oprah Winfrey Show in Chicago.

In February 2001, Tillman was sentenced to six years in prison for a 1996, attempted murder and voluntary manslaughter charge, and released from custody in 2002.

[4] In July 2004, Tillman was sentenced to 37 months in prison after pleading guilty to federal identity theft charges.