As Always Dreaming came around the far turn in the April 1 Florida Derby and appeared to lose a touch of momentum, Anthony Manganaro wondered if he'd made a terrible mistake.
Less than two weeks prior, the Crownsville businessman had paid a sum that "made me blanch" for a minority piece of the potential Kentucky Derby contender. And if Always Dreaming proved no match for top competition, Manganaro would watch that money go right down the drain on the dirt at Gulfstream Park.
"I would've looked pretty stupid," he said.
As it turned out, Manganaro had nothing to fear. Always Dreaming proved to be the best horse that day, and he was even better five weeks later at Churchill Downs.
A winter gamble has become a smashing spring success. And Manganaro, 73, gets to welcome a Kentucky Derby champion to his backyard for the 142nd Preakness.
"It's definitely special as a Maryland guy, having the Derby champ and watching him come to the Preakness," he said Thursday.
Manganaro grew up in a blue-collar suburb of Boston and moved to Maryland in 1981. He built a successful real estate development company, best known for the ezStorage facilities that dot the Baltimore-Washington landscape.
About nine years ago, Manganaro was ready to cede control of the business to his son. He wanted to do something entirely different, so he hopped a plane to Kentucky, snapped up 220 acres of pristine land and built a horse farm.
He believed he could blend old-school breeding methods with his new-school love of data to create a successful operation. And with 26 broodmares and a growing list of stakes winners, Siena Farm is on the way to fulfilling Manganaro's ambitions.
For him, taking a horse to the track is a secondary joy. His greatest fulfillment comes from finding the right mare-stallion blend to produce a brilliant thoroughbred.
"I think it starts with the majesty of the breed for me," he said.
He also loves thinking about how cutting-edge technology might introduce the sport to younger generations who've drifted away from racing. Imagine, he said, if you could use virtual reality technology to raise a foal on a Kentucky farm or guide a Derby contender through the field of 20 at Churchill Downs.
Given such far-reaching dreams, his decision to invest heavily in an established 3-year-old was unusual. But Manganaro had heard sensational buzz about Always Dreaming's Florida workouts. And he had sent his own horses to the colt's trainer, Todd Pletcher.
He has the highest regard for Pletcher, whom he said could "run General Motors."
"I was evaluating Todd's reaction to the horse as much as anything," he explained. "And I think Todd looked at Always Dreaming as a special horse from the beginning."
So he talked to his friend, Terry Finley, the CEO of West Point Thoroughbreds, about buying a piece of the rising colt. Both men knew Vinnie Viola, who owned Always Dreaming with his childhood friend, Anthony Bonomo.
"He'll never do it," Finley told Manganaro.
Actually, Viola would, for an unspecified but hefty price.
Pay it, Manganaro said, going with his gut. And the deal was complete five minutes later.
Though a Triple Crown run was never his driving ambition in the thoroughbred business, Manganaro has relished the last seven weeks. He's formed deeper bonds with the other members of Always Dreaming's sprawling ownership group, and he'll host 80 friends and family at the Preakness on Saturday.
"I must have gotten a lot friendlier," he said. "Or more handsome."