Bobcat Montgomery was an exceptionally quick-fisted lightweight who fought many great matches with Beau Jack, Ike Williams, and others. He turned pro in 1938. Bobcat won recognition by the N.Y. as World champion after beating Beau Jack in May 1943, but lost it in a rematch in November of that year. In the days when suspensions were not automatic, Montgomery lost via knockout to Al "Bummy" Davis in 63 seconds. Less than a month later, he fought a rubber match with Jack and re-won the title.

After win the title he had tough fights against Cecil Hudson, Tony Pellone and Allie Stolz, bere losing a unification bout to Ike Williams.

In 1995, Montgomery was inducted into the International Boxing Hall of Fame.