LOUISVILLE, Ky. -- The Boston-to-his-core horse owner did a slight double take when he saw a New York Giants cap in the same frame as his Kentucky Derby contender.
That's what you get when you put a Long Island guy at the center of a heart-tugging Boston sports story. Donald Little Jr. laughed Thursday as he recalled seeing the photo of his longtime friend and thoroughbred trainer, Jimmy Jerkens.
"I called him up instantly and said, 'What the heck are you doing?' " Mr. Little said.
The Giants cap was a small trade-off for Mr. Jerkens' expertise in guiding Wicked Strong, Beantown's favorite thoroughbred hopeful, to today's running of the Kentucky Derby.
It's hard to imagine one colt melding more story lines into a single Kentucky Derby narrative.
Wicked Strong represents Boston, through both his name and Mr. Little's promise to give 5 percent of the colt's Triple Crown winnings to victims of the 2013 Boston Marathon bombings.
He also represents Mr. Jerkens, a second-generation New York trainer who suffered the greatest disappointment of his career when he had to scratch a potential Derby favorite, Quality Road, just five days before the 2009 race.
Finally, the colt represents the wild hopes of 28 investors from around the country, few of whom have any experience in the thoroughbred game.
"It's a great story," said Mr. Little, who has spent his entire life around racing. "It carries a great cause. And this is great for the sport. It will bring people in."
Until a few weeks ago, not many thought Wicked Strong was the horse to pull it off. He was talented but performed poorly in Florida this winter, acting fussy in the starting gate and killing any buzz about Derby contention.
He was an afterthought going into the April 5 Wood Memorial, the traditional final Derby prep for New York 3-year-olds. There, Wicked Strong turned the story on its head with a commanding 3 1/2-length victory. Suddenly, he went from nobody to a popular second choice behind expected Derby favorite California Chrome.
As he watched the Wood unfold, Mr. Little thought, "This is just where we want to be right now."
The four weeks since have been a disorienting rush for Wicked Strong's connections, none of whom are used to this large stage.
Mr. Jerkens, 55, keeps a modest stable of 23 horses in New York. He learned the game from his father, Hall of Fame trainer Allen Jerkens, who brought three horses to the Kentucky Derby and fell short each time.
The younger Jerkens is an understated character who seems uninterested in the hype of Derby week.
"I'll be glad when it's over. I'll put it that way," he said. "There are so many distractions. You want to pay attention to your horse. You're away from your [home] barn for a long time. That's a little unsettling. But it's exciting, too, I admit."
Perhaps he's wary because his biggest career heartbreak is associated with this race. Mr. Jerkens said he'd never worked with a horse so gifted as Quality Road. When he had to scratch the Florida Derby champ because of a hoof injury, he was devastated. That devastation only deepened when Quality Road's owner, Edward Evans, dumped Mr. Jerkens in favor of leading national trainer Todd Pletcher.
"Losing him was the biggest downer," he recalled. "It was really unfair."
He has another shot at the Derby because of a 30-year relationship with Mr. Little that began with their fathers.
Mr. Little, 54, was born and raised in Boston. His grandmother rode steeplechase and his father, Donald Sr., got his first horse at age 16. The elder Mr. Little started Centennial Farms in 1982 with several investor friends from Wall Street.
Donald Jr. grew up around the game, playing professional polo into his mid-30s and joining the management of Centennial Farms in 1987. From his father, who died in 2012, he learned a straightforward business style and a belief in racing as a canvas for "hopes and dreams."
He also inherited a relationship with the Jerkens family. Allen Jerkens was his father's first trainer. And Donald Jr. has continued a similar relationship with Jimmy Jerkens, who handles all of Centennial Farms' New York horses.
Wicked Strong was an early example of a new business model for the operation, with Mr. Little soliciting investors to cover the colt's $375,000 price tag at the September 2012 yearling auction at Keeneland.
Moyne Spun was the colt's name at the time, but that would change a few months later, after Mr. Little watched his beloved city endure the terror of the Marathon bombings. He remembered learning the news from an email, informing him that a close friend who'd run in the race was uninjured. He was angry, then touched as he observed Bostonians coming together in the following weeks.
Mr. Little sought to rechristen the horse Boston Strong, but that name was already taken. So he plucked the popular Boston adjective wicked to achieve the same spirit.
In that light, donating a portion of Wicked Strong's winnings seemed fitting.
Of the 28 partners who own the colt, 20 have no background in racing. Mr. Little guffawed when asked if the novices believe racing investments always turn out this well. He joked that he already has his sales pitch ready for the next horse:
"If they say to do this twice is very difficult, I'll say 'Well, we did it once, so there's a good chance we'll do it a second time. You have to stick around.' "