His former girlfriend and the mother of his daughter, Molly, had been murdered, Dutrow said. His father, well-regarded Maryland trainer Richard Dutrow Sr., had cancer and would die in 1999. And his personal habits were problematic: He had been suspended for a year in Maryland in the early 1980s for repeatedly being found in possession of marijuana at the track, he was ruled off New York Racing Association tracks for five years after testing positive for marijuana later in the 1980s and he would have his license revoked again for five weeks in 2000 after another positive marijuana test.
"I needed to go through that," Dutrow said of his months in the barn. "I loved every minute of it. I had my microwave, my cot, my fridge, my TV and my horses. That's all I needed."
Said Vinny Marchione, the waiter who would help change Dutrow's fortunes: "He always spoke about being his own worst enemy and getting himself in trouble. He'd say, 'I'm good at the barn. It's when I leave the barn I get in trouble.'"
But Dutrow did leave the barn occasionally to eat at Vincent's Clam Bar in Little Italy, where Marchione befriended him. A former commodities trader on Wall Street who had gone through some tough times of his own, Marchione was into racing. He and Dutrow hit it off, and he wanted to help Dutrow get his career going, so he offered to arrange a meeting with a deep-pockets Wall Street guy named Sandy Goldfarb.
Goldfarb was big into the trotting game and just diversifying into thoroughbreds. Dutrow was dying for an owner who would give him some cash, give him some horses and give him a chance.
"Rick had a flawed past, but he always had talent," Marchione said. "I thought, 'Maybe his other demons are gone.' So I arranged for Rick to meet Sandy."
Goldfarb told Marchione he'd send a limo to pick up Dutrow for dinner. Marchione told Goldfarb to send the limo to Barn 1 at Aqueduct.
"It was hard for me to explain to Sandy that the guy I wanted him to give a million dollars to lives in a barn," Marchione said.
Once the two met, Dutrow took it from there, as he recalled this week.
"What's your angle?" Goldfarb asked him.
"You're looking at it," Dutrow responded.
Goldfarb eventually was sold and started sending Dutrow horses. It's been a blazing ride up the ladder since.
They won a single stakes race together in 2000. In 2001 and 2002, Dutrow was the leading trainer in New York by wins, and Goldfarb was the leading owner. Since then, Dutrow's client base has grown, and his bank account along with it. He has more than 700 wins since 2000, including the 2005 Breeders' Cup Classic with Saint Liam and two other Cup victories.
Dutrow said he bet $160,000 on Saint Liam to win in that race, pocketing more than $380,000. He's promised to drop a bomb on Big Brown on Saturday, too, as will the colt's sprawling connections. (More than 100 people are expected in the Big Brown party.)
"He'll be 8-5," Dutrow said, before his colt drew the highly unfavorable No. 20 post.
An 8-5 line was highly unlikely anyway for a horse with three career starts. Even Empire Maker, the much-hyped favorite in 2003, didn't go off at 8-5. He said that virtually the only thing that could keep him from winning the Derby is a bad break out of the gate and insisted that starting gate would not be a factor.
But Dutrow bravado is par for the course. He's been a dreamer since those days sleeping in the tack room.