One of the most decorated amateur boxers in US history, Bentt won four New York City Golden Gloves titles, five United States Amateur Boxing Championships and three (New York State) Empire State Games gold medals. After having won the bronze medal at the 1986 World Amateur Boxing Championships and the 1987 Pan American Games he placed a controversial second-place finish at the 1988 United States Olympic Trials and Box-off's to the Seoul Olympics eventual Gold Medalist, Ray Mercer. Sport writers frequently misspelled his second name, writing "Bent" or "Bennet" instead of "Bentt," and after he defeated Tommy Morrison, HBO's host Larry Merchant ironized in a way that he's finally have to add the third "T" to his name.