The two met when Jessica called up Jan on the recommendation of her then-trainers, Mike and Emma Winter, who were relocating to England. “The long drive to Virginia has proven to be well worth it,’ laughs Jessica, 27, who was living in Alabama at the time. ‘I had no idea what a difference she would make in my life.”

Originally from London, ON, Jessica has lived in the States since the age of five and is now based in Gladstone, NJ. She developed an interest in horses while attending elementary school, where there happened to be a barn on the property – every little girl’s fantasy. Fast-forward almost ten years and she was showing avidly in the hunter and jumper rings, eventually tackling her first event at the age of 18. She was first named to the Canadian Eventing Team long list in 2006, is short-listed in 2012 and hopes to be selected for the Canadian Olympic Team this summer in London.

Her mount for Rolex was High Society III (Trevor), a horse found by the Winters in 2005. “I was looking for a horse that would do a CCI** and maybe do a couple of advanced,” she recalls, “I ended up getting much more and could not be more thrilled with what he has done for me.” Jessica and Trevor began working with Jan once they graduated to the three-star level. “After working with Jan for a short period of time, she and I agreed this was a once-in-a-lifetime horse. She has been a huge part in further establishing Trevor and I at the three- and four-star level.”

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