Chester is a 17-time U.S. Equestrian Federation Four-in-Hand National Champion, and regularly ranks in the top 3 for FEI world rankings. 

He has won 4 silver medals at World Equestrian Games, and a historic team gold—in 2018 at the WEG in Tryon.

When he was 18 years old, Chester was the youngest driver to be named to the United States Equestrian Team for the World Pairs Driving Championships in Beesd, the Netherlands.

Chester serves on the USET Board of Trustees, the USEF High Performance Driving Committee, the National Driving Committee, the Safety Committee, the Hearing Committee, the Licensed Officials Committee and the Driving Technical Committee

 Live Oak Stud in Ocala Florida serves as Chester’s home and Team Weber’s base of operations when not on the road.