The Great Portrait Artists, by Celia McGee

I was in my Matisse mode,” Hilary Cooper says with a laugh, discussing her 2008 portrait of Jane Brown Grimes, the first female head of the United States Tennis Association. Cooper had asked to paint Grimes in a knee-length cherry-red coat she’d worn when presenting Roger Federer the champion’s trophy at the U.S. Open. Commissioned by Grimes’s father, Hazard Gillespie, éminence grise of the law firm Davis Polk, the portrait is typical of Cooper’s bright, spare-as-all-New-England style. Depicting Grimes seated in an armchair, the picture conveys her athletic prowess and inner strength.

Cooper is a popular portraitist in her three home bases— New York City, Aspen, and Lakeville, Connecticut— and she prides herself on being able to draw out even her most reluctant subjects. “I like being with people,” she says. “I’m not one to sit alone. It’s a joy to portray another person. It’s a privilege, and it suits me.”

During her previous life, in leveraged buyout financing and corporate cash management, Cooper took classes at the Art Students League. As commissions began to accumulate, she quit banking in 1987 to paint full-time. Cooper, who has done portraits of a number of high-profile figures, says many commissions arise from— and lead to— friendships. Her portrait of Louis Begley, the distinguished lawyer and author, for example, came about after they got to know each other at a club they both go to. Another portrait, of Oliver Dobbs (now a CIO at the London hedge fund CQS), was a gift for his wife. Cooper later painted her as well, and a close friendship now exists among them all.

Cooper enjoys the challenge of developing a rapport with her sitters, be it a prickly Ed Koch, now one of her biggest fans, or a restless Peter Matthiessen, the novelist, adventurer, and Zen master whom Cooper painted in his priestly rakusa. “I reminded him that he sits still for forty-five minutes at a time when he meditates,” Cooper says. “So much of portraiture is an abstraction of visual experience— the process of discovering who someone really is.”