Former Politician Named CEO of Wilmington’s Most Powerful Nonprofit

Dan Winslow has mellowed out.

Asked if he would still be “spicy” as the New Hanover Community Endowment’s new president and CEO, he said, “As I’ve gotten older my tolerance for spice has gone way down.” 

Fifteen years ago, Winslow was a rising star in the Massachusetts GOP. Smart, ambitious, and with politics in his blood, he had already served as a judge and general counsel for Gov. Mitt Romney before winning a seat in the state house in 2010. Winslow was politically moderate in a way that looks almost liberal in 2024: a fiscal hawk who backed gay marriage and drove an electric car. But his theatrical style was anything but moderate.

When Winslow introduced himself to the press this week, he acknowledged that some of us had already Googled him, likely finding what the CommonWealth Beacon dubbed, the “Dan Winslow Show.”

That includes the pyramid of marshmallow fluff that Winslow once left outside a state finance official’s office, 10 containers of it, each with a suggestion on how to cut—you guessed it—the fluff from the budget. Or Winslow’s feisty presence on what was then Twitter, comparing state leaders to Kim Jong Il and calling U.S. congressional leaders from both parties “idiots” who needed “psychotherapy or an enema.” 

By 2013, after an unsuccessful primary run for Senate, Winslow resigned from office to join the private sector, building a sizable legal team for a tech firm. In 2021, he moved to the nonprofit world as the president of the libertarian-leaning New England Legal Foundation, which apparently aspires to do for “individual economic liberties, property rights, and limited government” what the ACLU does for civil rights.

These days, Winslow’s social media account has been deleted—at least for now—but that doesn’t mean he’ll have nothing to say.

“I hope to remain quotable—but I hope to remain substantively quotable,” he said.

There will certainly be plenty to quote him about. On October 1, Winslow is set to take the reins of the $1.3-billion community foundation, created by the county’s contentious sale of New Hanover Regional Medical Center to Novant Health. 

Winslow inherits the position from William Buster, who was ousted in February over differences regarding the endowment’s future. He also inherits a fraught relationship with the public, as the endowment has consistently struggled with community engagement, messaging, and projecting a clear sense of direction.

For six months, the endowment has been thinking about what it wanted to see in its next leader, and they’ve no doubt considered how the next CEO would handle these issues.

So far, Winslow’s answer is that he doesn’t know. His first plan of action, he said, is to listen. 

On his first day at work, he committed to sitting down with the Endowment’s Community Advisory Council, who have publicly said they’ve been sidelined. He also said he’ll listen to staff and the board on issues like transparency, communication, and staffing. (The endowment, Winslow acknowledged, only has “network officers” for half of its four pillars of investment.) 

Winslow said he wants a lean, effective foundation that can leverage corporate and private sector dollars to maximize impact. But he offered no concrete plans.

“I don’t want to come in with ideas necessarily before I’ve had the chance to speak with people,” he said on Monday. “I know that some folks have been unhappy. I hope to learn from those people. I hope to learn from any kind of constructive criticism.”

Winslow’s already faced some of that criticism, especially from Heal Our People’s Endowment, the organization created by former Wilmington mayor, one-term Democratic state senator, and hospital sale critic Harper Peterson. In a social media post, the group credited the “good old boy network” for picking a “‘free market’ ideologue.” It also called Winslow’s dearth of philanthropic experience a “slap in the face.”

Peterson has been critical of the board’s increasingly white, male, and conservative makeup, an issue he’s brought to N.C. Attorney General Josh Stein, who is currently running for governor. The former senator isn’t quite a one-man army: His group’s petition criticizing the endowment’s direction and urging Stein’s intervention has collected more than 1,200 signatures.

But with a few exceptions, Stein has declined to get more involved, and his office has nothing to say about the hiring of Winslow, a 66-year-old white male conservative, as CEO of a foundation serving a region known for significant racial and economic disparity. 

And it’s true that, unlike Buster, Winslow has no philanthropic background. Asked about it, he said he’d learned a lot on the nonprofit side of things, applying for grants, and that he would lean heavily on the endowment’s existing staff to get up to speed, adding that he’s a “quick study.” 

For someone about to run a billion-dollar foundation, that sentiment might not inspire confidence—especially in critics like Peterson. But, at the same time, it’s not clear that’s even something the endowment was looking for this time around.

Introducing Winslow to the public on Monday, endowment Chair Bill Cameron reflected on the CEO search process, saying board members had put together a “great list” of qualities they wanted to see. He said they, of course, understood no single candidate from the pool of over 150 would meet every criterion. 

Then, with a subtle flourish, Cameron added, “Let me tell you something, we found a candidate who met every damn one of them.” 

I followed up with Cameron to ask him if Winslow checked every box, does that mean philanthropic experience wasn’t one of them? Cameron didn’t answer my question, instead sending a statement saying Winslow’s background “creates the right mix of skills needed to drive transformational change in our community.”

A press release the endowment’s PR firm distributed on Monday claimed Winslow’s career will provide a “fresh perspective.” And while that definitely has the fingerprints of corporate spin on it, it feels premature to judge things conclusively before Winslow has spent a single day at the office. He could surprise his critics, as he did in the Massachusetts House. He might even push back on the endowment board itself, now and then.

Who knows how spicy things might get if Winslow still has the stomach for it?

Ben Schachtman is the news director for WHQR in Wilmington and co-author of our weekly newsletter on the Cape Fear Region, The Dive.