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Rollin’ Hard began training in the mid-90’s at Danny Davis’ wrestling school but soon fell under the tutelage of Ian Rotten, who continued training him. He debuted for Rotten’s IWA organization in late 1996 under the moniker “Tornado Taz”, but would start using the name “Trustworthy Taz” by years end. He wouldn’t start using the Rollin’ Hard name until April of 1997, when he was used in a far more prominent role.
Rollin’ would come to the ring using a mixture of popular African American themed sitcom themes and a gigantic afro that would often grow larger by the week. While originally hated by the IWA crowd, antics like calling himself the “Food Stamp Champ” won fans over and soon he was among the IWA’s most popular homegrown stars. By the end of 1997 he’d win the IWA Television title and participate in the companies first ever death match tournament, making it all the way to the semi-finals before losing to Ian Rotten.
Rollin’ remained one of the IWA’s main performers for close to seven years and would win both the Heavyweight and tag team title three times. Eventually though Rollin’ would be used less and less as IWA Mid-South began focusing less on the hardcore wrestling aspect of their company. His last regular appearance was on October 23, 2003 in Scottsburg, IN. He made his IWA Mid-South return, for one night only, on September 16, 2004 in New Albany, IN. Outside of the ring he was a sports coach for local children.
In October of 2005 Rollin’ was diagnosed with colon cancer and was rushed into surgery where Doctors removed a large portion of his colon. He underwent chemotherapy for six months, from November until May 2006. Even before he finished his treatment he was planning on making his return to wrestling, which he did on April 21, 2006 for IWA Mid-South. On that night he’d go on to win a bunkhouse battle royal to receive a bye in the 2006 edition of the King of the Death Matches, which were to be held on June 2 & 3 in Plainfield, IN. Rollin’ would go on to be eliminated from the tournament by longtime friend and partner Mitch Page.
Things continued to look up for Rollin’ as test in August came back showing him to be clear of cancer. His wrestling career though didn’t pick up as he had hoped and after the King of the Death Matches he was not being used by IWA Mid-South, which disappointed him. Another blow came when his Doctor told him he needed ankle fusion surgery and that he’d never be able to wrestle again.
Like with everything else, Rollin’ would surprise Doctors and fans alike when he made his return at the 2007 edition of the King of the Death Matches on June 22, 2007. He’d go on to wrestle for IWA Mid-South four more times, having his last match there on March 1, 2008 in Joliet, IL. Less than two weeks later he’d find out that the cancer had returned and that this time it was not curable. He was given 18 to 24 months to live.
In addition to radiation and chemo treatments, Rollin’ underwent surgery on 7/16 to remove parts of his gallbladder, spleen, pancreas and bowel system as a precaution in response to fears that the cancer had spread. His condition deteriorated so much after the surgery that he was placed on life support on 7/21. Rollin’ though continued to fight and his condition improved until eventually he was able to be taken off of it. Still his overall condition continued to deteriorate and little could be done about it.
In his short life Roland Montgomery gave himself to wrestling fans, the wrestlers that grew to see him as a brother, the kids he coached, and his family. His contributions to all of those should not be forgotten, because his story deserves to inspire as many people as possible. That would be a fitting outcome for the fighter that was Rollin’ Hard.
“This sh** might get me in the end, but as of right now I have control over it and I’m gonna take full advantage of it. I’m gonna LIVE HARD till i cant live anymore.” – Rollin’ Hard