Flaherty had roles in films and miniseries such as Lonesome Dove, Natural Born Killers, Book of Shadows: Blair Witch 2 and Signs. He also had a brief role in Men in Black 3, and appeared as Jack Crow in Jim Mickles 2014 adaptation of Cold in July. Other film appearances include Winter People, Millers Crossing, Blood In Blood Out, Tom and Huck and Home Fries while television roles include guest appearances on The Equalizer, New York News and White Collar as well as a two-episode stint on The Education of Max Bickford as Whammo.

Flaherty was a graduate of Pontotoc High School, and attended University of Southern Mississippi after high school. He resided in New York City.