Soul brothers

Chappaqua doc + homeless artist = two lives transformed

A Chappaqua doctor, a homeless man and a chance encounter outside Yankee Stadium that would transform both of their lives.

It was after the New York Yankees’ defeat of the Houston Astros on June 22 of last year that Jeff Gilbert, M.D. – an ob/gyn who is the medical director of STIs at BioReference Labs in Elmwood Park, New Jersey — noticed a man selling prints of his paintings of baseball players and other athletes outside the ballpark. Gilbert purchased a picture of Yankee right fielder Aaron Judge for his office, then lamented not getting one he saw of New York Giants’ running back Saquon Barkley. The next time Gilbert was at the stadium, he searched for the artist but to no avail.

Looking more closely at the Judge print, he found a website and then a phone number and that was the beginning of an odyssey and a relationship. Gilbert discovered that the artist, Michael Bailey, though homeless, would travel back and forth between his hometown of Chicago and the Bronx, selling his wares. Over dinners at Yankee Tavern and his own home, Gilbert learned more about Bailey, who would go on to the World Series and the Super Bowl to ply his trade. He wasn’t always well-treated.

“I told Michael that I would see to it that he didn’t have to sleep on the street ever again,” Gilbert – author of the children’s book “Milton’s Moment,” about kindness – writes in a piece called “Adoption.” “I would put him up in a motel or a hotel for the rest of the baseball season and then wherever he would be as he journeyed across the United States, selling his work outside of baseball and football stadiums from coast to coast.”

In March, Gilbert got Bailey an apartment near Yankee Stadium where the artist spends his days painting and Gilbert visits weekly, bringing groceries and supplies donated by others. You could say Gilbert is a patron of the arts. But he sees himself as something, someone, else.

“Michael is my brother. It is good that he is able to pursue his artwork in the safety of his apartment. I am confident that (post-pandemic) he will be out there again displaying his talents. Until that time, he knows that I will continue to be there for him. As I tell him, ‘You ain’t heavy, you’re my brother.’”

Bailey will exhibit his work Aug. 8 from 9 a.m. to 2 p.m. at Bobo’s Café in the Chappaqua Metro-North station, 1 Station Plaza. For more, visit and…/.

Georgette Gouveia


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