(Originally published in the June 11, 2011 issue of The Blood-Horse magazine. Feel free to share your own thoughts and opinions at the bottom of the column.)    

It took more than 60 years for William Gregory to realize his boyhood dream of training Thoroughbreds. Seven years ago, the retired Gregory obtained his trainer’s license, and at Hollywood Park May 26 he won his first race, at age 78. He not only trains Charlie’sboywins, he and his wife, Nancy, bred and own the 4-year-old California-bred gelding.

Charlie’sboywins is named for Gregory’s father, Charles, who rode show horses in Kentucky, but refused to allow his son to become a racehorse trainer. Yet Charles’ profession introduced young Billy to racing.

“I grew up in Fulton, Ky., and we’d always go to county fairs,” said Gregory. “All of the fairs back then had racetracks, and I thought it was so thrilling to watch. We’d be sitting on the rail and almost get our heads ripped off as the horses raced by.”

Billy attended the University of Kentucky, his college days cleaved by service in the Korean War, and he went on to vet school at Auburn University. The idea of racehorses continued to intrude, however, whether he was helping collect urine samples at the Red Mile harness track or meeting Spendthrift Farm’s Leslie Combs II when Gregory worked part-time measuring tobacco.

“I had to go up to the house to see Mr. Combs,” Gregory recalled. “He asked me if I wanted to see a real racehorse, and he showed me Nashua.”

Only after Billy graduated from vet school did his father reveal the reason behind his aversion to the racetrack.

“I told my dad, ‘I’ve gone through college, a war, and vet school—why can’t I be a racetrack vet?’ He said, ‘There’s a bad element on the racetrack.’ I told him, ‘There’s a bad element everywhere.’ ”

Gregory began his veterinary career as a large-animal practitioner in Kentucky. But he had seen California’s ocean and mountains when he went through the state en route to Korea, and decided he wanted to live on the West Coast. In Northern California he worked as a large-animal vet until, while traveling to a Sunday morning call for a horse, he injured his leg in an auto accident. He switched to a small-animal practice.

“When he retired,” said Nancy, “I pushed him to go to the track and hang out with the track vet at Hollywood Park just for something to do. He loved being at the track and thought about getting his trainer’s license, but he felt he was too old.”

Nancy was having none of that and told him, “It’s never too late to be what you might have been.”

Once Gregory did get to the backstretch, instead of the bad element his dad warned him about, he found a helpful one. Trainer Gary Lewis spent time teaching him about being a trainer. Leonard Duncan, Kristin Mulhall, and Jack Van Berg have also aided him along the way.

It hasn’t been easy financially. The Gregorys work in the mutuel department servicing self-serve betting machines to help pay for the horses.

They bought Spanish Gypsy, the dam of Charlie’sboywins, from Lewis and boarded her locally. She produced Gregory’s two current runners—Charlie’sboywins, by Fruition, and Philly Slew, by Corslew.

Charlie’sboywins has been a particular challenge.

“There’s not a bad, vicious bone in his body,” Gregory said, “but if he doesn’t want to do something, he won’t.”

While Charlie’sboywins enjoys racing, he’s not keen on the work he must do to get fit. One morning on the Hollywood training track, he simply sat down. It took four pony horses to get him up and back to the barn. Gregory now works him with horses on either side so that he thinks he’s in a race.

Before Gregory could get Charlie’sboywins to the races, the trainer suffered a stroke last August and lost the sight in his right eye for four months. Gregory had the gelding in Van Berg’s barn.

“Jack was there during Bill’s stroke,” said Nancy, “and we owe him an enormous thanks for all his help.”

The gelding finally began his career last December at Hollywood. In his first six starts, he finished second twice and fourth twice.

“I knew he was knocking on the door,” said Gregory. “We’d always run him short, and Gary suggested we try him a little longer. So we ran him at seven furlongs.”

Kerwin John, who had ridden him twice, to a second and a fourth, was aboard again.

“I told Kerwin, ‘You’ll be blessed if you can get him to settle,’ and he did,” Gregory said.

Charlie’sboywins came from last to nip favored Red Dwarf right at the wire in the maiden claiming race.

“He’s very special,” said Gregory. “We’ll probably try a starter allowance race next.”

Of course, Gregory is looking to the future. After all, his dream career has just begun.