Evan Shipman Jackson, Successful Trainer Who Gave Up A Career At The Track For Life In Florida Keys, Dies At 88 by Ray Paulick|01.22.202201.28.2022|9:02pm4:59pm His biggest horse was named Mr. Right, who defeated the mighty Damascus by a nose in the 1968 Woodward Stakes. But training Thoroughbred racehorses in the modern era turned out to be the wrong profession for Evan Shipman Jackson, who quit the game in the early 1990s and spent the last 25 years of his life operating dive boats in the Florida Keys. Jackson died in Key Largo, Fla., on Jan. 7, failing to wake up after taking an afternoon nap. Active until the end, gardening and riding his bike around town, he was 88 years old. Born Aug. 13, 1933, in Keswick, Va., Jackson was named for his uncle, the esteemed horse racing writer Evan Shipman. He grew up around horses in the Charlottesville, Va., area where his trail-blazing mother, Mary, operated a riding school on her farm. Mary Jackson did a lot of buying and selling of show horses and was referred to in one article as “Saratoga's most unique buyer” at yearling sales in upstate New York. Evan Jackson would become a steeplechase rider in his teens and rode at various meets throughout the Midatlantic region into the early 1960s – his riding career interrupted while serving in the U.S. Army during the Korean War. Jackson transitioned to trainer when his riding career ended and within a few years was winning big races on both coasts. Mr. Right, owned by the wife of bandleader and pianist Peter Duchin, was his first major horse, winning the 1968 Santa Anita Handicap. The victory made the son of Auditing the first New York-bred to win a $100,000 race and a stakes in California. Mr. Right went on to beat 1-10 favorite Damascus by a nose in the 1968 Woodward Stakes and shortly thereafter was sold for $400,000 to a partnership that included singer Frank Sinatra. For Sinatra and his partners, Jackson sent Mr. Right out to win the Trenton Handicap and Suburban Handicap in 1969 before the horse went to stud. Other major stakes winners followed, including Acorn winner Cathy Honey and Haskell Handicap winner Gladwin – both for Californian Hastings Harcourt in 1970. Others included El Cajon Stakes winner Quick Bluff in 1973; G2 Del Mar Handicap winner Redtop III in 1974; G1 Century Handicap winner Winds of Thought in 1976; Grade 1 Flower Bowl Handicap winner Rossard (Den) in 1984; and Grade 3 Affectionately Handicap winner Descent in 1985. Jackson's two daughters, Tara and Kelle, remember their father training for celebrities both in New York and later when he moved his stable to California. “I remember the time a limo came to our house in New York to pick my dad up for dinner and it was Frank Sinatra,” said Tara Jackson. Summers in Del Mar were special for the trainer's children, who lived with their mother most of the year on the East Coast after their parents divorced. “We would rent a beach house for six or eight weeks and it was so much fun,” Tara Jackson said of their Del Mar summers. “That was when you could take horses from the track over to the beach. My dad loved loved his horses and loved doing that.” “Those summers were exciting,” remembered Tara Jackson. “Dad was playing tennis with Farrah Fawcett and Lee Majors and he trained for Burt Bacharach and Angie Dickinson. He got his pilot's license and I remember he would train in the morning and fly us to Mammoth Mountain to ski in the afternoons.” But everything wasn't rosy with Evan Jackson. “He had a very strong will, was an old-school horseman and a big animal advocate,” said Tara Jackson. “He butted heads with owners and didn't like the direction the game was going. I remember listening to him and (the late Hall of Fame trainer) Allen Jerkens lamenting the lack of long-distance races. He hated it when he started seeing horses brought into the paddock with lip chains. Racing simply didn't fit him any more and he said he'd rather be with any animals over most humans.” Jackson quit training and went to work at a ski resort in Taos, N.M., then landed in the Florida Keys, where he worked air traffic control at a small airport and eventually began operating dive boats. “My Dad walked away from the only thing he knew as an occupation and way of life – because anyone that works in Thoroughbred horse racing knows it's a way of life not just a job – because he couldn't fall in line with what he saw happening,” Kelle Jackson said. “He was a quintessential horseman – which worked well when horse training was a craft and a sport – when the horse mattered and intuition, observation and personal judgment were more important than the business, more than the person with the heaviest pocketbook. But times started changing and the quintessential horseman became not as important as the business. He knew his horses personally and he treated them as such. He admittedly had some regrets in life but he was a man that was driven by 'to thine own self be true.' “My dad was not an easy man to deal with when he was sure he was right about something,” Kelle Jackson continued. “And I'm not so sure owners appreciated that or that he could find the right balance to allow for some change in the industry while doing what he thought was best for his horses. He chose his own personal integrity over the work that was so near and dear to him for decades and that he was born into.” In addition to daughters Tara and Kelle, he is survived by a son, Evan Jackson Jr., by Kim Welchel, his daughter from a previous marriage, and by nine grandchildren and nine great-grandchildren. An animal lover throughout his life, Jackson is also survived by his beloved cat, “Trim,” who he adopted as a stray many years ago in Key Largo. Trim has been taken in by a group of people that lived in the same community as Jackson for the last 17 years. Kelle Jackson said her father's wishes were to be cremated and have the ashes spread at his childhood home in Keswick, Va. That will be done this spring.