Business owner/philanthropist Michelle DiFebo Freeman has overcome challenges with gumption and generosity

By Lynn R. Parks  |  Photograph by Carolyn Watson
From the May 2017 issue

may-MichelleFreeman A Model of Resiliency - Delaware Beach LifeOn a mantel in the Freeman home in Potomac, Md., sits a candlestick that was once used as a prop by the Washington National Opera. The candlestick was last on stage 16 years ago, when it sat on a desk during a production of Mozart’s “The Marriage of Figaro.”

In the audience for that performance — seated in one of the boxes at the Kennedy Center Opera House — were Sussex County residents Joshua Freeman and Michelle DiFebo. Josh was on the board of the opera company, a seat that his father had held before him, and Michelle, part of a large Italian family, had grown up listening to opera.

“It was Christmas,” Michelle recalls. “The opera was in the first act” — lead characters Figaro and Susanna were preparing for their wedding, which was to take place later that day. “There was a moment when the music was quiet and all of a sudden, Josh was on one knee, asking me to marry him. It was really beautiful. I said, ‘Yes.’ And then we left.”

The couple had been going out off and on for seven years. On their second date, Michelle, who had a then-3-year-old son, asked Josh if he ever intended to marry. “He didn’t have to say that he was going to marry me,” she says. “But I didn’t date willy-nilly. Being married and having a family life was important to me. If he didn’t plan on marrying, then I wasn’t interested in dating him.”

Josh told her that that was “the weirdest question” anyone had ever asked him on a second date. But he said that yes, he intended to wed someday.

Later on in their courtship, Josh had a couple questions of his own. Would Michelle convert to Judaism? The answer was no. And would she move from her home in Delaware to Maryland, where he was working for the Carl M. Freeman Cos., a development business that his father had started in 1947?

“I told him, only if we were engaged,” she says. “I was selling real estate and had an interesting career. I had great friends and had just bought a new house in Salt Pond,” a development near Bethany Beach. “Unless it was moving forward into something meaningful, I wasn’t leaving. I had my core values and I was not going to give up who I was and all the things that I had worked for.”

But on that evening in the Kennedy Center, knee-deep in the magic of Mozart, Christmas and romance, none of that mattered.

“I knew that I wanted a life with Josh,” Michelle says. “We had worked so hard to be together and all of a sudden, religion, where we were going to live — none of that mattered.”

They were married in 2001. And five years later, after the births of their two children, Josh was killed in a helicopter crash near Dagsboro. He had been at a Christmas party at one of his company’s properties, Bear Trap Dunes, in Ocean View, and was headed back to the western shore. It was a foggy night, state police said at the time. Also killed in the crash was the helicopter pilot, Alisa Danielle Howell.

Josh was just 42. Michelle immediately stepped up to take care of the business, which has offices in Rockville and near Fenwick Island. After three years of “getting up to speed by serving on the board,” she took over as president and CEO in 2009.

“There were people who suggested that I should give it up: sell the company and take the money. Just put on a sweatshirt and curl up somewhere,” she remembers. The wife of an associate went to her office one day after work to ask when she was going to step aside and let someone else run the company.

“‘When are you going?’ she asked me,” Michelle says. “I told her, ‘Never.’ And I said that if there were people who were waiting for that, maybe they should go work someplace else.

“I knew that if I didn’t step in and be present, the legacy of the family and all of the people who worked there would be at risk.”

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