George began racing as a young boy, and he was quickly determined to make cycling his career. George won 10 junior national titles and two world medals prior to joining the professional ranks. The following 19 years brought victories in a record 17 Ronde van Vlaanderen races and a second-place finish at the grueling Paris-Roubaix, which was the best placement of any American. George also competed 17 times in the Tour de France and won three U.S. National Road Race championships, making him one of the best known riders in the world.

In 2012, George retired from the professional racing circuit, but he continues to be directly involved in product development for Hincapie Sportswear and the racing team. From assisting in the selection of riders to accompanying the team on training rides to securing sponsorships and funding, George has played an integral role in the advancement of the team.