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John Scheinman has covered horse racing for the Washington Post for six years. He got the gig at a time when the sport and the whole realm of turf writing were thick with a doom-and-gloom aura.

That aura remains. But to hear Scheinman talk about his job, he’s the luckiest guy since Lou Gehrig got Lou Gehrig’s disease.

“At times, maybe I feel like I could do more substantial work with my life,” says the 40-something Northwest resident. “But I feel like I have one of the coolest jobs there is. It’s a treat to be able to cover racing, even though racing’s dying, and I feel like I’m hitting my stride as a writer.”

He caught the racing bug after reading Post legend Andrew Beyer’s peerless how-to books as a student at American University. Since Beyer took a buyout from the paper in 2003, Scheinman has covered the game as a beat writer would—he’ll be in Louisville all this week to prepare readers for the May 6 Kentucky Derby. But he’s technically a freelancer for the paper. Scheinman supplements his Post paycheck by moonlighting as a boxing commentator for Comcast and as a copy editor for a suburban newspaper.

The racing assignments, however, allow him moneymaking opportunities that his other jobs don’t: He can wager while he works.

And, like pretty much everybody who goes to the racetrack for work or play or whatever reason—and as Beyer did quite famously while in the Post’s employ (“Windows of Opportunity,” Cheap Seats, 6/4/2004)—Scheinman does wager.

“I’m not a wild gambler, not by any means,” he says. “But I bet.”

As racing’s high season begins this week, he’ll be celebrating the first anniversary of his biggest score and the cementing of what he, with a chuckle, calls “the legend of John Scheinman.” On last year’s Derby Day, surrounded by turf writers from around the globe, Scheinman struck gold at the press-box betting window.

Scheinman’s greatest day at the track didn’t really get started until the 10th race on the Churchill Downs card. He had been scouting all 20 three-year-olds in the field since winter. In his writings and chats for the Post in the days before the big race, he had steered readers away from the consensus favorites, George Steinbrenner’s Bellamy Road and cancer-charity darling Afleet Alex, and toward Sun King, a horse that went off at 16-1.

But just before post time, as the field loitered and “My Old Kentucky Home” blared over the track public-address system, Scheinman had an epiphany. It involved the No. 10 horse, a 50-1 longshot named Giacomo.

“Every horse I liked looked dead,” he says. “I didn’t like Giacomo, but he was one of the only horses in the field that looked good at all.”

Scheinman went to the window and got a $1 Pick Three ticket—an exotic wager requiring a bettor to select the winners of three consecutive races—selecting Giacomo to win the Derby and a pair of no-name longshots—British Attitude and Grand View Cliffs—to win the 11th and 12th races on the Churchill Downs card, respectively.

Bellamy Road and Afleet Alex were indeed dogs that day. Giacomo, however, came in. No tout of renown had predicted the winner correctly. After the race, Scheinman couldn’t find anybody in the press box who bet on Giacomo, either.

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Scheinman learned long ago that nothing builds credibility among racing scribers quite like picking a winner. “When I started with the Post, it was an honor and a privilege just to get to work with Andy Beyer, my hero,” says Scheinman. “But Andy never really would talk to me. Then one day at the track I shot my mouth off that a horse named Jorgie Stover was going to win the Maryland Million Sprint, and that horse killed ’em at 25-1. From that day on, Andy talked to me.”

So Scheinman flashed his live Pick Three ticket to others in the Churchill Downs press box and got a lot of attention for it. But if his other horses didn’t come in, that ticket was only worth the paper the numbers 10-2-9 were printed on.

Scheinman spent the next hour and change facing a problem that writers who cover football or basketball or golf never face.

“As soon as the Derby ends, the press box is a beehive of activity,” he says. “Everybody’s getting down to crafting their leads, and they’ll fill in the quotes later. Giacomo wins, and nobody’s got him but me. So now I’m paying attention to these absolutely worthless races that follow the Derby and still trying to file a first-rate story.”

The deadline wordsmithing only got harder when British Attitude won the 11th by nearly eight lengths at 13-1 odds.

“Everybody in the press box is coming up to me to see the ticket,” he says. “And I’m thinking, Don’t you know there’s a job for me to do here?”

Everything came down to Grand View Cliffs in the 12th, and this gelding was no gimme: The morning line listed the horse at 12-1. Three horses hit the wire at about the same time. Grand View Cliffs was declared the winner by a head.

Scheinman has had good wagering/cred-building days before. In 2001, the first Derby he covered for the Post, he had talked up, written about, and even bet on huge longshot Invisible Ink. He cashed “about $5,000” worth of exacta and place tickets after Invisible Ink finished second.

And at the 2004 Belmont Stakes, he went against the hearts, minds, and wallets of pretty much every racing fan and writer in the country by betting on Nick Zito’s Birdstone instead of 1-2 favorite Smarty Jones.

“All the writers at the Belmont wanted Smarty, because they’re going to finally get the chance to write about a horse winning the Triple Crown,” Scheinman recalls. “And as the horses come down the stretch, everybody in the press box is looking down at the track, their necks craned looking out this long window, and Smarty’s in front, and you can hear all these reporters saying, ‘Come on Smarty! Come on Smarty!’ All of a sudden, there’s this other horse coming up, and this other horse comes across ahead of Smarty, and I see it’s my horse. So while everybody in the whole place lets out this big groan, I sort of pump my fist quietly, and this one woman looks at me and says, ‘You didn’t.’”

But it was nothing compared to his Derby Day haul. The last Pick Three of the day was worth $14,972.10.

“Suddenly, it was like I was the story,” he says. “A writer for the Louisville Courier-Journal, the home paper there, came out and said, ‘We want to write about you!’ It dawned on me how weird this was, and I was like, ‘No! No! No! Not even a sidebar!’ I didn’t want to be the story that day, and I started having all these visions of people following me out to the parking lot. I think I was freaked out by having a roll of 149 tightly folded-up $100 bills in my pocket.”

Scheinman’s Derby score keeps alive a tradition among Post scribes of coming up big in Triple Crown races: Legend has it that Beyer cashed in for $80,000 at the 1984 Belmont.

Scheinman met his Post deadline and made it home with all his money. He doesn’t say where it went but suggests that a chunk of that Derby Day wad has been donated back to the racing industry at betting windows over the past year.

Asked to pick a winner for the 2006 race, Scheinman says he’s heading to Louisville intending to throw a few bucks on Maryland-based longshot Sweetnorthernsaint. But, as his Pick Three from last year proves, there’s plenty of time to change his mind.

“I’ve been at this for a while now,” he says. “But it all is still fascinating for me, and I’m integrated enough that people in racing actually recognize me now, and that amazes me. I guess if I look around, I have to say that I’m one of the top horse-racing writers in the country. There’s just not that many left.”—Dave McKenna