Women of Substance & Style: Michelle Freeman

by Virginia Coyne


Charles M. Freeman Companies President and CEO Michelle Freeman, photographed at Charlie Palmer Steak in Washington, D.C.

“I believe service to others can heal a broken heart.” It is with those words of conviction that Michelle Freeman began the 18-minute TedX talk she gave in Wilmington, Del. last December. The result was part confessional (she discusses her struggles with addiction, being a single mother in her 20s and living on food stamps), part road map for becoming whole again after suffering unspeakable loss. “It felt like a story I needed to get out there,” she says. “There are dark times in everybody’s life and when you turn to service to another human being, there is some repair of your soul,” she says today.

The darkest of times came in 2006 when Freeman lost her husband, real estate scion Joshua Freeman, in a helicopter accident. Still in shock, she was handed the reins to the family business, the Carl M. Freeman Companies, as well as Carl M. Freeman Foundation, which provides grants to nonprofit groups.

She subsequently began the Joshua M. Freeman Foundation in southern Delaware to honor her late husband, a music lover. The non-profit operates Freeman Stage at Bayside, an entertainment venue near the beach, and brings art and music into schools that otherwise would go without.

Tragedy would strike again eight years later, when her new love, Matt Haley, a chef and humanitarian with whom she thought she would spend the rest of her life, died after being struck by a truck while riding a motorcycle through India.

Devastated and broken, she turned to service once again to help her get out of bed in the morning. Only two weeks after Haley’s death she attended an event to raise money for THEARC in Anacostia. Her head and heart weren’t in it, she says, but it proved the impetus for her to continue her mission of giving. “As human beings, if we can take the very times we are the neediest, that we feel we need to be taken care of and become a giver, it’s transforming,” she says in her TedX Talk. “It’s magical. And it frees you.”

Michelle’s Style: An entire section of Freeman’s closet is devoted to the color red — pants, sweaters, coats and shoes. As a minority partner in Monumental Sports and Entertainment, which owns the Washington Capitals and Wizards, she takes “Rocking the Red” as seriously as the fans.

Fashion is fun for her now, she says, which hasn’t always been true. “AftervJosh died, I wore suits all the time. They became almost like armor for me,” she says. “There was so much coming at me — so much pain and so much sadness that when I buttoned the suit it almost kept the world from hurting me.”

Today, she’s more adventurous. “I wanted white boots and I said to myself, you know what, at 51, I can wear little white boots and I can have some fun with my fashion. I take chances that I probably wouldn’t have taken even five years ago.”

This story appears in the April 2018 issue of Washington Life Magazine.

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