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Talk about long-term relationships. When North Carolina residents Frank and Ann Loving bought Double Bill, Ronald Reagan was president, a first-class postage stamp cost 20 cents, Amadeus won the Academy Award for Best Picture, and Spend a Buck won the Kentucky Derby.

Double Bill at age 31It was 1985, and the Lovings ventured to Ocala, Fla., at the behest of bloodstock agent Bill Thomas to consider a 2-year-old son of Nodouble and the High Echelon mare Queens Way. Ann Loving still vividly remembers that first impression of the now 31-year-old gelding.

“He was training with an exercise rider on him, and this gal was strong. He basically ran away with her that day. We could just see that there was a whole lot of potential in this horse. So we bought him and sent him straight to Jonathan Sheppard, which was obviously good fortune for us and good fortune for Double Bill. He started him out on the flat and then took him into steeplechasing.”

Double Bill was based at his trainer’s Ashwell Farm in West Grove, Pa. Sheppard–who happened to have another stellar 2-year-old named Storm Cat and legendary jumper Flatterer in the barn at that time–campaigned the Lovings’ purchase throughout the Mid-Atlantic region. Consistent and useful, Double Bill hit the board in his first 10 efforts. He made 15 starts on the flat, winning twice, before Sheppard switched gears and sent him out over jumps as a 4-year-old in July 1987.

Peruse his lifetime past performances, and you’ll see Double Bill’s name listed more often than not. From that summer of 1987 until April 1995, the chestnut gelding took his connections to every major meet on the steeplechase calendar.

“We went to see him a lot,” Ann Loving said. “In fact we had a motor home, and the front of it said ‘Chasin Racin.’ That was basically what we did. We’d take that motor home in the summer and go from one race to another. It was fun, and I can say we were owners who recognized their horse; often that’s not the case. But when we went down to see him in the shedrow we didn’t have to be told which horse was ours. We knew.”

Double Bill made it worth their while. Topping his list of achievements were back-to-back wins in Saratoga’s prestigious New York Turf Writers Handicap in 1989 and 1990 under Ben Guessford. The pair returned to defend in 1991, finishing third behind stablemates Yaw and Moon-struck. But more stakes followed, with scores in the Delta Air Lines Cup Handicap and Crown Royal Handicap in 1992. At age 10 in 1993, he won the Coca Cola Handicap and repeated in the Crown Royal, winning by 8 lengths while earning the comment “Much the best” on the chart.

When 12-year-old Double Bill went postward for the final time at Tryon’s Block House meet in April 1995, his resume boasted 75 starts with placings of 15-16-14 and $476,826 in his coffers. Not once did he run for a claiming price, and Sheppard was at the helm for every bit of it.

According to the trainer, Double Bill’s sense of self-preservation very likely contributed to his longevity.

“He was a classy horse and he was very durable. He was a pretty smart horse; I would say that one of the reasons he stuck around for so long was that he probably took care of himself just a little bit. I think he had the credentials to be a slightly better horse on the flat than he was, but when he switched to jumps, he just seemed to get his competitive spirit up. And obviously he couldn’t have compiled a record like he did if he wasn’t pretty determined.”

Sheppard went on to say that the horse had so much natural ability that things came easier to him than to many of the horses he ran against. But when things weren’t going exactly to his liking, Double Bill would back himself out of the equation rather than risk mishap or injury.

“At that time we were for-tunate enough to have a pretty strong group of horses over jumps, and he was certainly one of the top members of that group,” Sheppard went on. “He was a tough old bird. Some horses are just so incredibly game and determined that they’ll just sort of run ’til the wheels fall off. I would say he wasn’t that type–he was going to give 95 percent to us and save 5 percent for himself. But he was very successful at a high level for a good number of years.”

The Fair Hill community is so rife with Sheppard protégés that it seems nearly every third or fourth person has some connection to Double Bill. Trainer Graham Motion, then groom to champion Flatterer, accompanied Sheppard and Double Bill to England and Ireland to race in December 1988.

“He was a lovely horse, very kind. I used to gallop him. I mean, everybody galloped everybody, but I was over in England with him for a couple of weeks,” Motion remembered. “We stayed at Bruce Jackson’s parents’ stables when our horses ran at Cheltenham. I got on him in the field behind Bruce’s parents’ house. There’s a really cool picture of Jonathan on Summer Colony and I’m following him on Double Bill–it’s at my parents’ and is one of my favorites.”

“Everybody” also included Motion’s chief assistant Adrian Rolls, who actually rode Double Bill in an allowance at Saratoga in August 1989 (they were third). Sue Kenny, Motion’s secretary, worked for Sheppard during that period and was also occasionally aboard Double Bill in the morning. And Fair Hill-based trainer Chuck Lawrence was in the tack when Double Bill ran in the Breeders’ Cup Steeplechase in 1991.

Furthermore, Guessford is frequently aboard horses at Fair Hill and his wife Mary works in the National Steeplechase Association office.

Double Bill is a long way from Fair Hill, a fixture on the Lovings’ 22-acre Burnt Chimney Farm in Tryon, N.C., just up the road from the scene of his last race.

“We love Tryon; we came here 20 years ago. We had a house in Palm Beach, Florida, and a place in Lake Placid, New York. We also had a breeding farm [Loving Way Farm] in Versailles, Kentucky,” Ann Loving said. “When we knew that we were going to get out of the breeding business and bring things off the track, we wanted to have a forever home for them, so we bought this place. We have a fabulous trail system here that’s a cooperative for landowners. It’s over 100 miles of trails. I can ride out in four different directions from our farm and ride all day. And Bill’s been on those trails, every one of them.”

In the 19 years since his racing career, Double Bill hunted with the Tryon pack, serving as a huntsman’s mount during a season. He did local hunter paces. He even performed on an ad hoc drill team with Ann Loving.

“That was the funniest thing he did. Some friends of mine got together, we were a real hodge-podge of horses but we had fun and he was part of it. We started out as a little quadrille and then got up to eight of us in it. Just getting together and we’d usually put on a little bit of a show for somebody, but it was just local stuff. Some freestyles to music and that type of thing.”

Loving said that Double Bill remained “very active” up until about three years ago, but even at this stage of the game she will take him out for a leisurely stroll on the trail a few times a year.

Also retired at Burnt Chim-ney are 23-year-old home-bred Bangguster, another former Sheppard trainee, and Will o’ the Wish, whom Loving refers to as “Bill’s longtime girlfriend.” Admittedly, Double Bill looks his age at 31 but still charges across the field to the fence when feed time arrives.

“He might not look great,” she said, “but he’s feeling good!”

/Maggie Kimmitt


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