The Executive Branch: Inside DC’s Most Controversial Private Club—and Its Unexpected Security Chief

When the Executive Branch opened its doors in Washington, DC last spring, the private club’s launch was immediately enveloped in a cloud of political intrigue and celebrity cachet. The club’s founding roster read like a who’s who of Trump-aligned tech and finance power players: Donald Trump Jr. as co-owner, Trump administration AI czar David Sacks, venture capitalist Chamath Palihapitiya, and crypto twins Tyler and Cameron Winklevoss.

“We wanted to create something new, hipper, and Trump-aligned,” Sacks explained at the time, as reported by Politico. The club positioned itself as a modern conservative hub, a place where MAGA-minded entrepreneurs and political operatives could network in style. But proximity to Trumpworld came with a hefty price tag—membership fees reportedly reaching as high as $500,000, despite the club’s basement location tucked behind a suburban shopping complex.

The initial press coverage identified Trump Jr. and his business associates Omeed Malik, Chris Buskirk, and Zach and Alex Witkoff as the club’s co-owners. Later reporting from Mother Jones revealed the involvement of David Sacks’ frequent business associate Glenn Gilmore, a San Francisco Bay Area real estate developer who holds multiple titles on official documents including co-owner, managing member, director, and president.

But corporate filings reviewed by WIRED reveal another key figure whose involvement has not been previously reported: Sean LoJacono, a former Metropolitan Police Department officer whose career took an unexpected turn from law enforcement to private club security.

LoJacono’s path to the Executive Branch is anything but conventional. In 2017, while serving as an MPD officer, LoJacono conducted a stop-and-frisk that would become infamous in Washington policing circles. The incident, captured on video, showed LoJacono questioning a man named M.B. Cottingham for a suspected open-container violation before conducting a body search that Cottingham later described as invasive.

“He stuck his finger in my crack,” Cottingham says in the viral YouTube footage. “Stop fingering me, though, bro.”

The American Civil Liberties Union of the District of Columbia sued LoJacono on behalf of Cottingham, alleging that LoJacono had “jammed his fingers between Mr. Cottingham’s buttocks and grabbed his genitals.” Cottingham settled his lawsuit with LoJacono in 2018 for an undisclosed amount paid by the District of Columbia, which admitted no wrongdoing.

The MPD announced its intention to dismiss LoJacono following an internal affairs investigation. While the Cottingham search was not deemed a fireable offense, investigators found another search LoJacono had conducted the same day violated department policy. By early 2019, LoJacono had appealed his dismissal, arguing in well-publicized hearings that he had conducted searches according to how he had been taught by fellow officers in the field.

The police union’s collective bargaining agreement enabled LoJacono to further appeal to a third-party arbitrator, which in November 2023 ruled in his favor. Rather than returning to the police force, LoJacono pivoted to private security.

A LinkedIn profile featuring LoJacono’s name, likeness, and employment history lists his current position as “Director of Security and Facilities Management” at an unnamed private club in Washington, DC, from June 2025 to the present. Official incorporation paperwork for the Executive Branch LLC, filed with the District of Columbia’s corporations division in March 2025—just before the club launched—lists LoJacono as the “beneficial owner” of the business. The address on the paperwork matches the Executive Branch’s location.

Donald Trump Jr. and other reported owners are not listed on this incorporation document; Gilmore appears as the company’s “organizer.”

The revelation that LoJacono is considered a beneficial owner raises questions about what this designation means for the club’s operations and governance. In corporate terms, a beneficial owner is someone who enjoys the benefits of ownership even if the title is in another name. This could indicate LoJacono has significant control over the club’s security operations or potentially other aspects of its management.

The Executive Branch’s security apparatus has become particularly relevant as the club has hosted high-profile events and political gatherings. With its Trump-aligned membership and location in the nation’s capital, the club has become a magnet for political activity and media attention.

Security professionals note that private clubs of this caliber typically employ former law enforcement and military personnel for their security teams. However, LoJacono’s specific background—combining a controversial police career with his current role overseeing security at one of DC’s most politically connected private venues—represents an unusual case.

The club’s other owners have not publicly addressed LoJacono’s role or his designation as beneficial owner. Attempts to reach the Executive Branch for comment were unsuccessful. Neither LoJacono nor representatives for the club’s other owners responded to requests for comment.

As Washington’s private club scene continues to evolve, the Executive Branch stands out not just for its political connections but for the complex web of ownership and management that underlies its operations. The involvement of figures like LoJacono adds another layer to the club’s already controversial profile, raising questions about the intersection of law enforcement, private security, and political networking in the nation’s capital.

The story of the Executive Branch—from its star-studded launch to its unexpected security chief—reflects broader tensions in Washington around power, access, and accountability. As the club continues to host influential figures and political events, the full extent of its ownership structure and operational control remains a subject of speculation and scrutiny.

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