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Dan Winslow has mellowed out.
Asked if he would still be โspicyโ as the New Hanover Community Endowmentโs new president and CEO, he said, โAs I’ve gotten older my tolerance for spice has gone way down.โ
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 โDan Winslow Show.โ
That includes the pyramid of marshmallow fluff that Winslow once left outside a state finance officialโs office, 10 containers of it, each with a suggestion on how to cutโyou guessed itโthe fluff from the budget. Or Winslowโs feisty presence on what was then Twitter, comparing state leaders to Kim Jong Il and calling U.S. congressional leaders from both parties โidiotsโ who needed โpsychotherapy or an enema.โย
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 โindividual economic liberties, property rights, and limited governmentโ what the ACLU does for civil rights.
These days, Winslowโs social media account has been deletedโat least for nowโbut that doesnโt mean heโll have nothing to say.
โI hope to remain quotableโbut I hope to remain substantively quotable,โ 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 countyโs contentious sale of New Hanover Regional Medical Center to Novant Health.
For The Dive, Ben Schachtman introduces the region to one of its most powerful leaders.
Former Politician Named CEO of Wilmingtonโs Most Powerful Nonprofit
Former GOP star Dan Winslow was named the New Hanover Community Endowmentโs new CEO. With no philanthropic track record, Winslow faces an uphill climb to win over skeptics.
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Ferry Tales

Last week, The Assembly detailed Lee Robertsโ quest to purchase the Bald Head Island ferry system through his private equity firm, SharpVue Capital.
Now that Roberts has been named UNC-Chapel Hillโs chancellor, he will no longer captain the SharpVue ship. But Robertsโ team continues without him: SharpVue attorneys were at the N.C. Court of Appeals last week for a hearing on the attempted sale.
SharpVue first agreed to purchase the system from the islandโs developer, Bald Head Island Ltd., for $56 million in 2022. But the small village government, which also wants to purchase the system, has impeded SharpVueโs hopes of smooth sailing. The village appealed the Utilities Commissionโs approval of the transfer to SharpVue last year, one of five active cases surrounding the future of the ferry system.
SharpVue would operate a monopoly system, the village asserts, with loyalty to investors rather than ratepayers. The village argues the commissionโs approval wasnโt strong enough to protect those most reliant on the system.
Village attorney Samuel Ervin IV asked the court to remand the case back to the commission and compel it to conduct additional fact-finding. โWe are not trying to re-argue the facts,โ he told the court.
Among other critiques, the village opposed the commissionโs authorization for future rate increases to keep pace with inflation. Typically, utility rate increases go through a separate and rigorous process, but by folding it in with a transfer, Ervin argued the commission is essentially letting SharpVue raise fees without proving necessity.
Bald Head Island Ltd.โs lawyer, M. Gray Styers Jr., told the court the relief the village is seeking is โliterally unprecedented.โ
After a four-day hearing, thousands of pages of documents, and a 35-page order, Styers said the commissionโs detailed analysis was sufficient.
Ervin criticized Styers for making verbal arguments not previously raised in the written record and urged the court to consider the importance of the case for life on the island. โItโs important that it be done right,โ Ervin said. โWe ask that you recognize the monumental consequences that this will have on the village.โ
The court will render an opinion in this case within the next few months. Its decision on another appeal related to the commissionโs ruling of regulating the ferry systemโs parking and barge operations is expected sooner.
โJohanna F. Still
Catch up on an audio conversation on last weekโs edition of The Dive here, or contact The Dive team with tips and feedback at johanna@theassemblync.com.
Around the Region
Wedge Issues: Democratic candidate for state Senate District 7 David Hill has threatened litigation against his competitor, Republican Sen. Michael Lee, over political ads about his position on gender-affirming care for minors. WHQR breaks down the issue.
Old Hanover: County Commissioners OKโd a $300,000 facility study to determine what can be done to fix the century-old New Hanover High School. The school will welcome students next week despite having several classrooms closed due to structural decay, Port City Daily reports.ย
New School: Most Brunswick County Schools will soon reach capacity, so the county recently transferred $1.2 million worth of property near its landfill to the school system, the Brunswick Beacon reports.
Around the State
Feeding An Army
Nearly one out of three Fort Liberty soldiers and their family members are food insecure. Can efforts to address it fill the gap?
The Last Dance of Tim Moore and Phil Berger
Republicans have failed to deliver on key priorities, and some blame a diminished relationship between House and Senate leaders.
Transition of Care
After passage of legislation restricting medical treatment for transgender youth, families are seeking care across state lines.

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