LOUISVILLE, Ky. -- Seven hours after Omar Jennings left his Catonsville home for his Kentucky Derby getaway, he was sitting before a big screen TV at Churchill Downs hollering for a horse named Dublin Assets.
He was hollering for a first-place finish. For a quick $80 payoff.
At his side were New York Leni, Mister B, Big Jeff and Dave the Rave, who each ponied up $700 for this weekend at America's premier racing event, the first jewel in the Triple Crown. Al the Hammerhead was there, too. But he needed to be on his feet, within an easy stride of the betting windows at Silks, a restaurant inside the track. Hammerhead -- Albert William Ford Jr. to most who know him -- preferred to watch the races on a bank of eight overhead screens.
Dublin Assets, the No. 2 horse, loped behind the finishers. Omie's boys were disappointed but not deterred. "The first race at Churchill Downs and already I'm in the hole, where I'm very comfortable being," says Jennings, the host of this party, who quickly picked up his racing program and began circling his selections for the second race.
That was Wednesday, and they finished the day a couple thousand dollars in the hole. Yesterday, their luck was changing.
Jennings bet three horses to win -- and there they were, out front and charging. As they crossed the finish line, Jennings was on his feet, his face flushed. "I got the triple, baby," he says, a combination bet that put about $500 cash in his pocket. "Tell my wife, go to the mall. I'll pay for it."
Jennings has been a regular at the Derby since 1985 when a customer at his Jennings' Cafi in Catonsville offered him box seats for the Run for the Roses. He didn't hesitate and plunked down $600 for the six-seat box. He invited five friends to join him. They rented a Winnebago -- "for the first and last time" -- and drove to Louisville for a weekend of betting, beers and Kentucky hospitality.
"I remember I had the winner, Spend A Bunch," says Jennings, 40. "You never forget your first winner at the Derby, and ever since I've spent a lot."
The box seats now cost him $1,500. "That includes a box for [Kentucky] Oaks day, too," Jennings says, referring to the Friday stakes race for fillies.
But coming to the Derby isn't about money. Winning or losing it. Although the way "Big Jeff" Moran tells it, "If you put a cockroach on the table, we'd put a bet on it."
Coming to the Derby isn't about the sport, although Jennings says it's in his family. His uncle trained a horse, Neapolitan Way, that placed second in the Preakness, Maryland's second gem in the Triple Crown.
It's about hanging with the boys under blue skies, the smell of spring and thoroughbreds in the air.
"We come to have a good time with all our friends," says Dave "The Rave" Baxter, a contractor from Clarksville. "We come to relax, to take the edge off, to leave all the problems at home."
"We come for the camaraderie. If we win that's a bonus," adds Jennings, in between gulps of his Miller Lite.
Two of the original six members of the group have since died. Another, Robert "Mike" Carney, had to cancel at the last minute.
"Here's to Mike," says Moran, raising a toast to the 60-year-old accountant from Catonsville.
"He sets the tone for the young folk. We really love him and miss him," confides Baxter, 38.
Leni Kern, who owns The Spot nightclub in Fells Point, joined the trip at the invitation of his future brother-in-law, Brian "Mister B" Higgins. This is Kern's first Derby.
"Leni's getting married in two weeks," says Higgins, "and he figured he better blow his money now."
Al "The Hammer" Ford strides over to the table. "I can't sit here," he tells his friends apologetically. Jennings teases him. "Al, you can't bet every horse at every track." But Ford was having none of it. He didn't come all this way to sit and drink beer. He left his wife home with their 7-week-old son Albert III to come to the Derby.
"That was part of the pre-nuptial," says Ford, of Catonsville.
On the big screen, horse No. 9, Sock Hop, rounds the bend.
"Come on 9. Come on 9," shouts Moran. "Come on home. It ain't over, baby."
But it was. The horse didn't hit the board.
"A lot of horse races is luck," says Baxter, "being at the right place at the right time. Not always the best horse wins."
"Not always the best man wins the money," adds Jennings.
But they gamble nonetheless. At night, they spend their money at a casino on the Ohio River just over the Kentucky-Indiana border.
"We did so good they got us a limo for the ride home," says Jennings.
Jennings has been a constant at the Derby for 15 years. He can't say the same for the Preakness, although he has attended the Baltimore race in years past. The city of Louisville has Derby fever, Jennings says, and it's contagious. "Every place you go, every restaurant, every bar, is Derby-oriented," he says.
Baxter joined the Derby run in 1992, having already attended the Preakness every year since he was 14. But the atmosphere in Kentucky is different than Maryland, he says.
"When they sing 'My Old Kentucky Home,' they really take it personally. Whereas in Baltimore I don't know how many people in Baltimore know 'Maryland, My Maryland.' "
Nevertheless, Baxter will be in his seats at Pole 16 on Preakness day, May 20. Moran can't yet commit.
"It depends," he says, smiling, "on how much money we have left."