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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.
Dan Winslow, pictured during his 2013 Senate run, will be New Hanover Community Endowment’s next CEO. (AP Photo/Elise Amendola) 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?
Benjamin Schachtman: All right, Johanna Still, thanks for being here.
Johanna Still: Thanks, Ben.
BS: Okay, so this week we wrote about Daniel Winslow, who's the new president and CEO of the New Hanover community endowment.
JS: You gave The Assembly readers and The Dive readers an introduction to this guy who is from Massachusetts – so we locally might not have any familiarity with him, and you got to meet him. You went to a press conference for his introduction, and you kind of laid out his background, and what shows up when you Google him, which is some sort of theatrical, interesting stunts from his past. Can you give us an insight into what some of those were?
BS: Yeah, one of the first things that will come up when you Google him, or if you talk to reporters from the Boston, Massachusetts area who covered him, is a – some called it a political stunt that he pulled. He created a tower of marshmallow fluff. If you don't know what that is, it's like a big gloop of semi-melted marshmallow that some people love on sandwiches, and he made a tower of this stuff. Each individual container had a sort of budget suggestion on it for cutting ‘fluff’ out of the budget. So this pyramid of fluff he put in front of like a state finance director's office. Fluff is also made in Massachusetts. So it was hometown proud, and it got, you know, it got noticed,
JS: And he was also very active on Twitter.
BS: That’s right, yes, the social media platform that was Twitter back in the early 20-teens, he referred to Massachusetts House leaders as Kim Jong Il, and he wrote sort of an open letter Tweet to congressional leaders of both parties, calling them “dear idiots,” and saying that they needed “psychotherapy or an enema,” and this was over sort of a fiscal debate that they were having in Congress at the time.
JS: So he's not boring. No one can say that. But he did tell you that he's mellowed out, right?
BS: He claims to have mellowed out. I asked him if he would still be spicy, and he said that his tolerance for spice has gone down as he's aged, so he's at least trying to present himself as being a more mature person. He has spent the last decade running a veritable army of international attorneys, and for the last three years, he's run a nonprofit, the New England Legal Foundation, which is to libertarian ideals, what the ACLU is to civil rights.
BS: So his past was in the state House of Representatives in Massachusetts as a Republican. So he has has these political ties, but as you pointed in your piece, it was, you know, on the more moderate end of Republicanism.
BS: Yeah, he was sort of, you know, independently minded. He broke with his own party on issues. He is still definitely a conservative. And one of the things he was involved in with the New England Legal Foundation was going after moratoriums on eviction during Covid, which they called unconstitutional. I was definitely a conservative talking point when we were dealing with lots of protections put in place during Covid. So yeah, he's a conservative. I don't think that's changed. I think his public style has been dialed back a bit.
JS: And aside from his political past, what you have garnered from reporting on this and what we've seen publicly so far is that, I guess you could say the controversy with his appointment is in his lack of philanthropic experience. Can you talk us through the search process that led to this selection, which will, as we'll point out, in case it's not clear to listeners, is going to be, this is already is the most powerful nonprofit in Wilmington. They're sitting on over a billion dollars in what was once public money. So his lack of philanthropic experience, for some people who are critical of it, is what you had pointed out previously, alled a quote “slap in the face.”
BS: Yeah, that’s Heal Our People's Endowment, it's a group created to ask for more oversight, in particular from Attorney General Josh Stein, over the Endowment, and it's led up by former Willington mayor and state senator Harper Peterson. In a social media post, they called it a slap in the face, and yeah, the consulting firm that the endowment hired Moss + Ross apparently worked through over 150 candidates, some of whom I spoke with on background. They described a very thoughtful, very thorough interview process, and people that we spoke to who are critical of this just couldn't understand, with a national search and 150 vetted candidates, how no one could bring either philanthropic experience or any sort of diversity aspect to this role. I mean, it's not to put too fine a point on it, but it is a conservative, older white man who is now going to be running the Endowment. It has galled people who have previously noted that the Endowment is getting increasingly more male, more conservative, and more white.
BS: Well, we know that Mr. Winslow is officially starting next month, and I know he has said he wants to start by a big listening and learning process. So I know that you and I will be staying tuned to see what that entails.
BS: Absolutely. All right, Johanna, thanks for being here.
JS: Thank you.
