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.
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.
Best of Chicago voting is live now. Vote for your favorites »
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.
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.
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.
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.
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.”
