“So, the next race comes up, and I have the eight.”

Joel Einhorn is telling the story of a Pick Four sequence he once bet on the races at old Roosevelt Raceway in New York.  The vivid details, the passion in his voice make it seem like something that happened last night.

It was 27 years ago.

“The horse’s name was Valuable Doughnut.  Like I would ever forget that name,” he chuckles.

Einhorn sounds like a human race chart when describing his 52 years of following the sport.  As he talks about this fateful night in 1985 at the Nassau OTB, he gives the names and numbers of the horses he bet and a play-by-play of each race.

“Valuable Doughnut sweeps by the field and wins in a laugher.  Paid $16.

“So, that gets me through three legs, and here we go with the final race,” Einhorn says.  “I have the seven, Penman.  P-e-n-m-a-n.  Roosevelt was a half-mile track, so as they’re coming around the second time, Penman, he tilts out and makes a move around the field, coasts all the way home.”

Einhorn is not telling this story to brag about his handicapping ability.  Sure, he’s always had a “knack” for handicapping.  But right now, he’s talking about pure luck.  Einhorn played a straight Pick Four of five-four-eight-seven.

“It was the last four digits of my telephone number,” he says in his unmistakably New York accent.

Einhorn cashes the Pick Four ticket for $13,000.

“You don’t always have to be smart,” he says.  “Sometimes, it’s just about being lucky.”

A week from Saturday, Einhorn hopes fortune smiles on him again, adding another unforgettable story to his collection.  The 68-year-old from Fresh Meadows, N.Y., won the chance to place a $100,000 win wager on this year’s Kentucky Derby Presented by Yum! Brands.  Einhorn was randomly selected to make the free wager through the Kentucky Derby DreamBet online contest offered by Churchill Downs, NBC Sports and CNBC for the third consecutive year.

Two years ago, Glen Fullerton of Houston won $900,000 after placing his bet on Super Saver at odds of 8-1.  Last year, Chicago’s Dave Flores fell just short when Mucho Macho Man finished third in the Derby.

Einhorn is taking his opportunity seriously.  Just not too seriously.

“Ultimately, I’ll put some names into a hat and pull one out,” Einhorn deadpans.  “I’m kidding!  That’s a joke!”

In reality, Einhorn, whose handicapping prowess landed him a spot in this year’s National Handicapping Championship in Las Vegas, is taking a systematic approach to seeking out the winner.

“First, I did away with all the preconceived thoughts that were in my head about this year’s field and started over,” he says.  “The horses that I would consider the top group – I’ve looked at all their races and their Brisnet past performances, and I’ve read as much as possible about them.  I’ve also reached out to very knowledgeable people to get their opinions.”

Those people include Dr. Steve Roman, creator of the Dosage Index, and long-time writer and handicapper Steve Davidowitz, CEO of GradeOneRacing.com.

“I’ve done some very good handicapping over the course of my life,” says Einhorn.  “We can handicap and know who to choose, but the running of the race, we have no control over it.”

An Unexpected Miracle

Like a lot of people, Einhorn’s love affair with racing began with one horse.

“The first time I saw Kelso run, it was July 1960,” Einhorn recalls about his first year visiting the track as a high school student.  “He ran in an allowance race that day and won by 12 lengths in 1:34 and one.  That horse hooked me.”

It also didn’t hurt that Einhorn’s first-ever bet was a winning one.  It was a Daily Double at Aqueduct.  It paid $54.

“I remember things like it was yesterday,” Einhorn continues.  “There was this claiming race – I can give you their names if you want – but these two horses ran neck-and-neck the whole way around the track.  In racing, there’s always something exciting happening.”

Einhorn was at Belmont for each of the Triple Crown victories of the 1970′s.  The Affirmed-Alydar stretch duel in the 1978 Belmont stands out in his seemingly photographic racing mind.

“The crowd was jumping around so much, the entire third floor of the grandstand started swaying.  It was incredible.  It was like we were having an earthquake.”

But Einhorn has also seen his share of bad moments in the business.  He was at Belmont when Ruffian broke down in the 1975 match race with Foolish Pleasure – and when Go For Wand suffered the same fate at the 1990 Breeders’ Cup.  His first foray into ownership, in the mid-90′s, didn’t go very well either.

“I named him Unexpected Miracle, which was perfect, since I didn’t think I was ever going to own a racehorse,” Einhorn says.  “But he was hurting from the get-go.  We didn’t win, and I didn’t have a whole lot of fun.”

Unexpected Miracle went 0-for-10 before Einhorn sold him.  In his first start with a new owner, the colt won by 13 lengths.

“He was running on Bute that day,” Einhorn recalls.  “He ran through his discomfort.  He had a checkered career after that.”

But Einhorn kept tabs on Unexpected Miracle and eventually purchased him back for $1,000 to ensure the horse had a proper retirement.  He’s now 19 years old, living a peaceful existence in New Hampshire.  Einhorn still gets reports on him.

“That’s as important to me as anything, that former Thoroughbred racehorses get saved and don’t end up in the slaughter house,” says Einhorn, who’s been involved since the beginning of the Exceller Fund, a rescue group started by racing fans in 1997.  The group was named for the 1970′s star, Exceller, who won 11 Group or Grade 1 races in North America and Europe. He never won a year-end championship but was inducted into the National Museum of Racing Hall of Fame.

Exceller was sent to slaughter in Europe at age 23.

‘I guess my luck is average’

After another bad ownership experience, Einhorn limited his involvement to partnerships, and he found some success.

“We had a lot of winners, a lot of pictures, a lot of fun,” he says.
Like everyone in the racing business, Einhorn has felt the swings of fortune.  He says his luck is “no better than anyone else’s,” but he seems to hold his own when it comes to serendipity.

“I saw a commercial for a chance to win the bet,” Einhorn says of the $100,000 wager.  “It wasn’t something I was thinking about at all.  I wasn’t planning to go to the Kentucky Derby.”

But he entered the contest, and he won.  As he heads to Louisville next week, his lips are sealed about who his horse might be.  Not a word.  He plans to tell no one until he announces it publicly during the Derby telecast on NBC.

“Once I reveal the horse, I’ll hear opinions from everyone about it.  I don’t need that stress.  I put enough pressure on myself.

“When push comes to shove, it’s going to be luck,” he says.  “If I have it down to four horses, I’m going have to choose one of them.  That horse is going to have to have a good trip.  A clean trip that gives me a shot at winning.  That’s all I can ask.”

Whether Einhorn gets the breaks this time or not, one thing’s for sure.  He’ll be able to tell you everything about the moment.