The second edition of the Real Rider Cup, a charity jumping competition that features racing personalities aboard ex-racehorses, had an entirely new lineup this year, but once again the individual winner came from the world of steeplechasing. Just like the 2017 winner, Mark Beecher, perennial leading steeplechase trainer Jack Fisher was the first rider on course and jumped clear in a time that no one could beat. Fisher rode former trainee Quite a Journey and was sponsored by the gelding’s previous owner, Mrs. Gil Johnston. They completed the course of a dozen 2 ½-foot obstacles in 1:03, six seconds faster than runners-up Katelyn Jackson, who rode Santa’s Playboy for sponsor Madaket Stable, and Penelope Miller, in the familiar robin’s-egg blue and brown of Marylou Whitney. The Real Rider Cup, which benefits the Retired Racehorse Project and the nonprofit Plantation Field—site of a prestigious three-day event in Unionville, Pa.—raised more than $21,000 in its first year. In 2018, donations soared to nearly $50,000. The 16 participants were organized into squads called Exercise Riders, Owners, Racing Analysts, and Trainers. The team with the lowest cumulative time was the Exercise Riders. One of its members was Sharon Dominguez, whose husband, three-time Eclipse Award-winning jockey Ramon Dominguez, was there to cheer on Sharon and her teammates Lorna Chavez, Jodi Murphy, and Paddy Young. Fisher, who was also a successful jump jockey, has won six straight national steeplechase training titles. When Quite a Journey didn’t pan out as a steeplechaser, Fisher gave him to Rachael Lively, who works for him, and the gelding is now being ridden by her 11-year-old daughter, Cassie.  It was a busy day for Quite a Journey, who had already competed in the Fair Hill Thoroughbred Show in Maryland on Sunday morning. He then made the half-hour van ride to the Real Rider Cup and traveled back to Fair Hill for another horse-show class that afternoon. Fisher said he schooled Quite a Journey a few times recently, “because my wife made me—she yelled at me and said I wasn’t taking it seriously enough.” He added, “The important thing is that it raised twice as much as the year before. It also brings more awareness to the Thoroughbred retirement program.” Katelyn Jackson helped organize and promote the inaugural Real Rider Cup last year, when she worked for one of its co-creators, Anita Motion. She is now with BSW Bloodstock, which advises and manages Madaket Stable. Her mount, 21-year-old Santa’s Playboy, once competed at the top level of three-day eventing and was a veteran of the 2017 Real Rider Cup. “I joked with Anita that I would only ride if they put me on a really good horse,” she said. Jackson said she knew that she and “Santa” weren’t going to be the speediest pair in the Real Rider Cup, so she shaved seconds by cutting corners and taking the inside routes—including the final jump on course, where Santa’s Playboy saw a big fence that was still in place from the previous day’s most advanced show-jumping division and pricked his ears.   “He was ready for it!” said Jackson. “We tried, but we still couldn’t catch Jack.” While Jackson had never ridden Santa’s Playboy until the morning of the competition, Penelope Miller got in a practice session the day before with her mount, Disco Elvis, which may have helped the pair go clear. “He got me out of a couple of bad spots,” she said. “He has the big Thoroughbred heart that is just so generous. He made me look better, which I appreciate.” Miller, senior manager of digital media for America’s Best Racing, rides at Riverdale Stables in the Bronx, where the school horses include Quarter Horses, warmbloods, and Thoroughbreds. “I love riding the off-the-track Thoroughbreds so much more than any other horse, because you’re not constantly asking to do something,” she said, echoing the sentiments of many eventers. “They want to do whatever it is you want them to do—you just have to figure out how to ask. Once they know what you want, they’ll give you the world. They’re just the most eager horses, and they all want jobs. They’re a joy to ride.”