Information Dreaming’s Story Starts With 2 Brooklyn Boys’ Trips At Horse Racing

Viola’s father was among the regulars who folded their newspapers and placed them in the seams of their seats to claim the seats as their own, a custom that is still part of the horseplayer’s code.

One job for the young Viola was to stand in front of the track’s tote board and watch for sudden shifts in wagering. It would help him understand numbers, and it was also “magical being next to your dad, as he was really committed to a sport he loved,” Viola said.

Through the years, Viola and Bonomo’s friendship continued, as Vinnie went to West Point and Anthony to Queens to pitch baseball for St. John’s.

“I just loved seeing him in that West Point uniform,” Bonomo said. “He actually represented everything I wasn’t — orderly, disciplined.”

They continued to dream, too.

“Growing up as kids, we’ve won a lot of Kentucky Derbys, but never in reality,” Bonomo said.

Both men built successful business careers.

Viola, an Army Reserve major, became a billionaire Wall Street trader and the owner of the Florida Panthers in the N.H.L. He was President Trump’s first nominee to be the secretary of the Army until he withdrew his name in February, citing an inability to extricate himself from business ties to meet ethics requirements. Bonomo made it big in the insurance industry and is the chief executive of Physicians’ Reciprocal Insurers.

When Viola decided to get into the horse business, he called his childhood friend Bonomo.

“I think we just knew, when we got together, something special was going to happen,” Bonomo said.

The horse that became Always Dreaming fell into the hands of the partners when Bonomo’s son, Anthony Jr., busted his father’s prescribed budget and bought the colt, the son of Bodemeister, for $350,000 at the Keeneland September Yearling Sale.

The elder Bonomo’s wife, Mary Ellen, fell for the colt and decided on a name that encompassed her husband, his friend Vinnie and their old neighborhood. Her father, too, was a horseplayer who would rather have spent a day at Aqueduct or Belmont Park than anywhere else.

“I just always daydreamed,” she said. “I probably daydream a little too much. Why don’t we just name it Dreaming? Everybody dreams of something, whether it’s a big event or special day, the birth of their child, winning the Kentucky Derby. So I just said, ‘Always Dreaming.’ It just took off.”

So did the colt on Saturday, jetting on a wet track to a largely uncontested two-and-three-quarters-lengths victory. They had their Kentucky Derby — this time for real.

Now, Viola and Bonomo say they intend to take Always Dreaming to the second leg of the Triple Crown, the Preakness Stakes, at Pimlico in Baltimore.

“My initial impression is he finished the race great,” said Todd Pletcher, the colt’s trainer. “He came back to the winner’s enclosure and seemed like he caught his breath pretty quickly. So, you know, I think, if he’s doing well, we’re going to go to Baltimore. I don’t think I’ll have to twist anybody’s arm on the other side of the table here to do that.”

No, he won’t. Viola and Bonomo want to go. Whom will their colt face? No one knows yet. Baltimore racing officials will hustle up some horses to fill the gate for the Preakness.

Can Always Dreaming win again? His owners know speculation is worthless and predictions foolish. A potential Triple Crown? They stiff-arm that notion — ask after Baltimore.

Mary Ellen Bonomo, however, can’t help looking ahead. Dreaming, even.

“When this horse has its first baby,” she said, “we will name it Keep on Dreaming.”

Why not? It worked once.