Winterhalder was born in New England, grew up in Connecticut, and moved to Oklahoma in 1975 after serving in the US Army. In Oklahoma he joined the Rogues Motorcycle Club and was a close associate or member of the Bandidos outlaw motorcycle club for more than twenty years.

In 1997 Winterhalder established the Oklahoma chapter of the Bandidos and was the high ranking member of the Bandidos responsible for the 2001 assimilation of a Canadian outlaw motorcycle club known as the Rock Machine into the Bandidos, which became the Canadian chapters of the Bandidos. Winterhalder left the Bandidos in 2003 to spend time with his family, pursue business interests and better manage his construction company.

Since 2005, Winterhalder has authored or co-authored books and produced DVDs on the Harley-Davidson biker lifestyle, and is the creator and executive producer of the Biker Chicz television series and the Living on the Edge DVD/television series. He is also a consultant to the entertainment industry for television shows and feature films that focus on the biker lifestyle [1], has been seen on Fox News (USA), the Discovery Channel (USA), National Geographic aka Nat Geo (USA, Australia, UK & New Zealand), History Television (Canada), the History Channel (USA & Australia), Global TV (Canada), Prime TV (New Zealand), the CBC Canadian TV evening news and been a featured author on Bravo TV's "The Word"[2].

Winterhalder has been quoted in magazines and newspapers such as the Seattle Weekly, the Austin Chronicle, the Sunshine Coast Daily in Australia, and UK The Guardian. In 2009 he was interviewed by Louis Velazquez on the UCW Radio Show.