Jennie Saville’s had a busy spring preparing three horses for the Land Rover Kentucky Three-Day Event, but as the spring season wound down, she was able to focus more on her up-and-coming horses like FE Connory.

Olympic medalist and steeplechase jockey Kevin Freeman said he had the best of both worlds he occupied simultaneously in the 1960s and ‘70s, explaining that his heart belonged at once to both eventing and jump racing. “But I loved steeplechase best of all.” Freeman said that, at surface level, the...