Zebra Art

A Chappaqua neighbor famously coined the phrase, “It takes a village.” When Dr. Jeff Gilbert befriended Michael Bailey, a homeless artist, he proved her words true.

Gilbert was on his way back to his home in Chappaqua after the June 22nd Yankee game when he spotted a shoeless man sitting on Babe Ruth Plaza surrounded by pictures of baseball player Aaron Judge and football player Saquon Barkley. He stopped to purchase the five-dollar Judge print, and as he boarded the train, he regretted not buying the Saquon picture. He tracked down the artist via the artist’s website – artofzebra.com – listed on the print.

The artist, 60-year-old Bailey, has been down on his luck and living on the street after a bad marriage, difficult partnership, bout of depression, and subsequent drug problem. Bailey, an architect with an MBA from the University of Chicago, opened the Zebra Gallery in 1990. In 1995, he expanded the Zebra Gallery, establishing Zebra Art, Inc., an art publishing and distribution business. “I had a million-dollar business, and I lost everything. It was going very well for a while. Then, with my divorce, and my son being taken away from me, everything went bad,” says Bailey.

Bailey grew up with his mother and his sister, Helen, in Chicago. Helen, who now lives in California, still maintains Bailey’s site. Bailey’s son, who lives in Tampa, stores some of Bailey’s original artwork. But since 2007, Bailey has lived on the streets of Chicago, New York, Dallas, Cleveland, and various other cities to which he’s traveled, trying to promote his artwork. “I’m trying to show my work,” relays Bailey.

A Friendship Forms

Gilbert became more than another person whom Bailey met in his travels. They became fast friends when Gilbert gave Bailey a copy of his children’s book, Milton’s Moment. “That was a gesture of friendship,” according to Bailey, who refused to take money for the Saquon print Gilbert wanted to purchase.

“I felt like I knew Michael from somewhere as soon as I met him,” says Gilbert, who just “knew Michael was a good person.” Overwhelmed by Bailey’s story and kind nature, Gilbert invited Bailey to dinner and then to visit him up in Westchester. “We have so many resources available up here. Things that Michael could never access on his own,” notes Gilbert.

A Supportive Community

But Gilbert couldn’t change Bailey’s life on his own. So, he reached out to his wide circle of friends and to the Chappaqua, Briarcliff, Pleasantville, and Armonk communities via FaceBook to tell Bailey’s story.

Thanks to the power of positive social media and community support, Gilbert witnessed “so many members of our community mobilizing to make a difference in this man’s life.” Helena Terilli, Co-President of the food pantry at the Methodist Church in Pleasantville, bought Michael almost $300 of new clothes. And the community has contributed almost $5,000 to the gofundme.com page that Gilbert established for Bailey.

“I meet a lot of people in different cities,” noted Bailey, “but it was Jeff who changed my life.” For the first time since 2007, Bailey is no longer sleeping on the streets. While he does not have a home yet, he is staying in hotels as he travels the country to show his work.

Thanks to Gilbert’s efforts, Bailey’s artwork is also being exposed to a significantly wider audience. In June, he was invited to show and sell his work in Pleasantville at Yogolicious and The Village Bookstore.

The opportunity to connect to more people and to show and sell his work to people who didn’t know anything about him six months ago, is deeply meaningful and life-altering for Bailey, who sees art as his spiritual calling. “Art is my gift from God. When someone buys a piece of art from me, I tell them that I am sharing this gift.” Bailey generously shares this gift with others, often giving children free prints of their favorite athletes, superheroes, or musicians.

Late this summer, Bailey spent some time in Chicago, working on a painting of the New York Yankees’ veteran pitcher, CC Sabathia. He showcased it at the table that The Rotary Club of Chappaqua donated to him for Chappaqua’s Community Day on September 14th. Gilbert also arranged for Bailey to show his art at the Chappaqua art gallery, The Art Closet.

Future Plans for Bailey

After Community Day, Bailey spent a few days selling prints outside of Yankee Stadium before he hit the road once again. He then returned to sell his prints at the Chappaqua Children’s Book Festival on October 5th. In the coming months, Gilbert will continue to look for “creative ways to help Michael.” No doubt, he will continue to rely on his “village” for help.