When Jonathan Sheppard was asked whether he wanted to take a 9-year-old who had tendon problems, hadn't run in several months and hadn't won since 2007, he was understandably reluctant. It's not that he didn't mind reclamation projects or working with older horses, but this one seemed particularly hopeless.
"My first thought was, 'How am I going to get out of this one?'" he said.
But something about Cloudy's Knight intrigued Sheppard. He remembered the gelding's game win in the 2007 Grade I Canadian International. With a horse that had once been that classy, perhaps Sheppard could bring him back successfully. If not, maybe he could turn him into a jumper.
The challenge stirred something in him. Not long after he first heard from co-owner Shirley Schwartz, Sheppard was preparing to welcome Cloudy's Knight to his stable. He was hoping for a useful turf horse. Against all odds, he wound up getting one of the most productive flat horses he has trained in a long, Hall-of-Fame career.
Cloudy's Knight might not have the star power of Zenyatta or Rachel Alexandra, but his 2009 season has been one of the more remarkable campaigns in racing history. At an age when he should have been well past his prime and coming off what appeared to be a career-ending injury, the old pro has won three stakes this year, earned $338,409 and missed winning a Breeders' Cup race by a nose.
"What this horse has done is absolutely amazing," Sheppard said. "It's mind-boggling. We haven't done anything too different with him. He's done it himself. It's that he's an amazing animal."
Before Sheppard entered the picture, Cloudy's Knight was based in Chicago and was trained by Frank Kirby. He had won nine races, none more important than the Canadian International, that year a $2 million race.
A year later, Cloudy's Knight, then 8, struggled mightily. In four starts, he failed to finish in the money. It seemed obvious that age and infirmities had caught up to him and that retirement was the only viable option.
But before completely giving up, the owners decided to consult with a veterinarian. He told them that the soft tissue injury in a hind leg had made remarkable progress and that perhaps Cloudy's Knight could run again. He also suggested that they try a trainer who trained horses in a style typical of Europe, where horses aren't stabled at racetracks and are often given long, slow gallops in fields an other open terrain. He figured that was the best fit for an older horse with problems. That's why they picked the British-born Sheppard, who trains off a farm in Pennsylvania.
"They sent me the horse and this enormous, rangy animal arrives," Sheppard said. "He's about 17 hands. We did start jumping him a little bit when he first came to get him legged back up. He took to the jumping quite well, but once we got further along we cut out the jumping because he was training so well. It looked like he still had some life left in him as a flat horse. In his works, he showed amazing stamina."
With Rosemary Homeister Jr. aboard, Cloudy's Knight made his comeback at Kentucky Downs. Sheppard had come to the conclusion that the gelding's greatest asset was his stamina, so he entered him in the mile-and-a-half Kentucky Cup Turf on September 19. It was the gelding's first race in 373 days and he had not won in 23 months.
He was anything but rusty. He won that day at Kentucky Downs by 1 1/2 lengths and one month later returned to win the Sycamore at Keeneland. At that point, Sheppard wasn't quite sure what to do next with the gelding, but a chance meeting with a turf writer changed that. Marty McGee, the Daily Racing Form's Kentucky correspondent, ran into Sheppard one morning at Keeneland and told him he thought Cloudy's Knight would be a good fit for the Breeders' Cup Marathon.
"I hadn't even thought of that," Sheppard said. "Marty put the idea into my head."
After discussing the situation with the owners, Sheppard decided to go for the Marathon, hoping that his turf specialist would handle the synthetic surface.
It worked. Cloudy's Knight ran a remarkable race, losing by just a nose. After that, he headed up to Canada, where he won the Dec. 6 Valedictory Stakes at Woodbine.
No matter what happens from here, Sheppard has pulled off one of the great all-time training feats. It's something of which he's understandably quite proud.
"It means quite a lot to me," he said. "To resurrect an older horse who had seemed to have lost a step and had a major injury, to bring him back off a long layoff and win first time out at a mile-and-a-half in a graded stakes, I take professional pride in that. It's also been something that has given me a lot of pleasure. It's fun to be around a horse like that."
The plan now is to give Cloudy's Knight some time off and gear up for some races in the spring. Sheppard has been so encouraged by what he saw from Cloudy's Knight this year that he plans to aim even higher in 2010.
"We might pick up the tempo," he said. "We might have a more ambitious schedule and point for some of the bigger Grade II and Grade I races on the turf."
No 10-year-old has ever won a Grade I race, so the odds of Cloudy's Knight taking a top-level race next year aren't good. But he's obviously not just any horse. The latest chapter of a remarkable story about a remarkable horse may just be beginning.
Bill Finley is an award-winning racing writer whose work has appeared in The New York Times, USA Today and Sports Illustrated. Contact Bill at email@example.com.