You can meet the richest people on the way to a horse race, especially if that race is the Kentucky Derby. Three years ago, on the first Friday in May, Thomas Allen Pauly was at O’Hare waiting for his flight to Louisville. Pauly, 45, is a Chicago artist who specializes in portraits of racehorses. He goes to the Derby every year so he can paint a picture of the winner and, hopefully, sell it to the horse’s owner.

Sitting next to him at the gate was a woman holding a hatbox.

“Are you going to the Derby?” Pauly asked.

“Yes, I am,” she said. “We have a horse in the race.”

Jeri Knighton and her husband, Sam, didn’t own a big stable, but they had the kind of runner that every owner, from George Steinbrenner to the grandstand gamblers who pool their money to buy a cheap horse, dreams about. The Knightons, builders from Elmhurst, bought Request for Parole when he was two as part of a five-horse deal with two owners who wanted to clear their stable. The Knightons got a steal: as Request for Parole grew, he won so many races and so much money that he earned a spot in the starting gate at Churchill Downs.

Pauly handed Knighton his card.

“If he ever wins a big one, I’ll give you a call,” she promised.

Request for Parole finished fifth the next day. The Knightons decided to enter him in the Belmont Stakes, but while training he fractured a bone in his left front leg. When he returned in February 2003 for a high-stakes race called the Donn Handicap, he finished dead last–he began bleeding internally in the middle of the race and later developed a lung infection. The Knightons sent him to his birthplace, a farm in Kentucky, for a four-month rest. He won a few races later that year, but mostly for small purses.

But some horses are just late bloomers: for every Seattle Slew, who won the Triple Crown at age three, there’s a Request for Parole. When he turned five last year, he “just exploded,” says Sam Knighton. His trainer, Stanley Hough, decided to run him on grass instead of dirt to see if it suited him better. It did, and he quickly began climbing the ladder. He won the Mac Diarmida Handicap, a Grade III race at Gulfstream Park in Hallandale, Florida. A month later he finished second, by half a length, in the Pan American Handicap, a Grade II race on the same course. The Knightons decided to run him in the United Nations Handicap, a Grade I race held on Fourth of July weekend at Monmouth Park Racetrack in Oceanport, New Jersey. The race had a purse of $750,000–the winning owner gets 60 percent of that, and the Knightons were building a new house in Elmhurst.

The day of the race the Knightons were hosting a family reunion at their cottage in Paw Paw, Michigan. Sam Knighton tuned the TV to the race and ordered everyone to hush.

“No one was saying a word,” Sam says. “He broke good, and his jockey kicked him up into third, third, third. I said, ‘Don’t get stuck on the rail.’ At the top of the last turn, he took off. Mr. O’Brien was on the rail, making a charge, and Request just started going, just explosively passing, and in the last 300 yards the house was exploding.”

“That’s the best sound,” Jeri said. “That announcer saying, ‘It’s Request for Parole.'”

It would be a lot easier to build that house now. Because Request for Parole was helping to pay for it, Jeri thought he deserved his portrait over the fireplace–they have a statue of Babe Ruth at Yankee Stadium, don’t they? She gave Pauly a call.

Pauly failed the one art class he took at Schurz High School on the northwest side. At 18 he was working as a file clerk at an insurance office when a friend took him to Sportsman’s Park to watch a horse his family owned. His friend’s horse won, and Pauly drew a cartoon of the victory that night. It occurred to him that what he really wanted to do was draw pictures of horses.

“I think my friend showed [the cartoon] to someone around the track, and they were interested,” Pauly says. “After that, I got my first commission to draw a horse, right out of high school. I got hooked. I got fired from the file clerk job because I called in sick to go to the track.”

He took a job as a repairman with Illinois Bell and began attending races two or three times a week to draw horses. His work got attention: the management of Arlington Park asked him to draw the jockeys, writers, and broadcasters who hung out there, and many of those portraits now hang outside the press box. Then, in 1989, the Illinois Thoroughbred Breeders Association was looking for someone to paint a portrait of Western Playboy, its horse of the year. Pauly was asked if he had ever worked in oils.

Sure, he lied.

The portrait was a success, and soon his paintings, as well as some photographs, were on sale at the Arlington Park gift shop. He was approached by some of the wealthiest people in the horse-racing world. The wife of jockey Shane Sellers commissioned a portrait of her husband winning the Breeders’ Cup Classic on Buck’s Boy. Pauly painted Ghostzapper, winner of last year’s Breeders’ Cup, and the horse’s owner, billionaire racetrack magnate Frank Stronach, bought the portrait. George Steinbrenner bought one of his harness-racing prints at a yearling sale. When Pauly asked him for a card, he says, the Yankees owner bellowed, “‘George Steinbrenner doesn’t carry a card!’ So I gave him a pen and a piece of paper to write down all his information.”

Through all this, Pauly has kept his day job, but lately painting horses has become more lucrative–he estimates that he’s now three years from retiring. By the time the Knightons called, he was commanding more than $12,000 for a portrait, producing between 10 and 20 a year from his Ravenswood studio, which is decorated with racing silks and press credentials from past Derbys.

In Woody Allen’s Hannah and Her Sisters, a cranky artist played by Max von Sydow tells a client who’s looking for a painting to fit above his couch, “I don’t sell my paintings by the yard.” Pauly isn’t so touchy–he’ll work with the money. It took him almost a year to finish the painting of Request for Parole because he had to wait until the fireplace was installed to figure out what size to make the picture.

In that time, the horse developed more problems. He ran a poor race at the Breeders’ Cup in Texas last October, finishing sixth. A chart in the Daily Racing Form said he was “tired,” but in fact he was sick. “The Texas weather was horrible–stagnant and still,” says Jeri Knighton. “He came down from refreshing New York. He had a pretty grueling campaign last year. He didn’t eat his food after the race. The trainer took his temperature, and it turned out he had a fever. They shipped him back to New York, and he spent a month in the clinic with pleural pneumonia. He was on an IV.”

Request for Parole returned to the races last month, finishing fourth in a race at Belmont Park and third in the United Nations Handicap last weekend. To date, he’s won $1.2 million for the Knightons. Of the 19 horses who raced in the 2002 Kentucky Derby, only Request for Parole and Perfect Drift, a gelding, are still active. War Emblem, the winner, was retired to stud three years ago. Medaglia d’Oro, who turned out to be the best performer from that generation, was finished last year.

The day after Request for Parole returned to the track, Pauly brought the 20-by-31-inch painting to the Knighton’s new house, an English-style manor Jeri calls “the house that Request built.”

Pauly asked Jeri to leave the parlor while he hung it up. When she walked back in, “I got the chills,” she says. “It’s just amazing to see such a true-to-life picture of our horse. The way he picked up Edgar Prado, the jockey, is just amazing. It’s just like a picture in the paper. The next day, I came downstairs and just said, ‘Oh, my God.'”

Ted McClelland’s Horseplayers: Life at the Track, parts of which first ran in the Reader, was recently published by Chicago Review Press.

Art accompanying story in printed newspaper (not available in this archive): photo/Joeff Davis.