Meet the Lawyers

Four outside law firms. $345,822 in invoices. The district already had lawyers.

Meet The Lawsuits explains the cases. This page explains who the board hired to fight them — and why the hiring is the strangest part of the story.

What a school district's lawyers usually look like

A school board appoints one law firm as its counsel, at its annual meeting. A statewide model policy spells it out: one firm advises the board on everything, and special counsel is the exception — brought in for a specific problem, usually on the regular counsel's recommendation.

Those firms specialize in school law. Ingerman Smith has represented school districts since 1937. Guercio & Guercio since 1956.

Massapequa has a firm like that. Guercio & Guercio is the district's regular counsel — it was still handling a routine appeal for the district in November 2025.

For its lawsuits, the board went somewhere else entirely. It hired four outside firms — and the deeper the fight went, the further from school law the hires got.

Sokoloff Stern — the normal hire

Sokoloff Stern is a Carle Place litigation firm. The board hired it in July 2023 to file the first mascot lawsuit. It billed $61,208.

School law is one of its eight practice areas. Its own website leads with municipalities, businesses, and insurance companies.

It also represented Wantagh, Wyandanch, and Connetquot in their mascot cases. Those districts lost, accepted the rulings, and moved on.

After a federal judge dismissed Massapequa's case in March 2025, the board escalated — and brought in three more firms.

Rigano LLC — the bankruptcy lawyer

Rigano LLC is a two-lawyer firm in Melville. One of its lawyers, James Rigano, is a former EPA enforcement attorney who practices environmental law. The other is Nicholas Rigano.

Nicholas Rigano's background, from his own bio: corporate bankruptcy and restructuring. Chapter 7 and Chapter 11 cases. Environmental litigation — PFAS, pollution, wetlands. He has published in bankruptcy journals and lectured on bankruptcy.

Nothing in his background is education law, civil rights, or the First Amendment. Massapequa was his first school-district client: his education-law work begins in the fall of 2024, with the regionalization fight.

He is now Massapequa's lawyer on the regionalization case, the federal bathroom-policy case, and the state-court mascot case. He bills $350 an hour, and he has billed $127,800 — more than any other outside firm. (The district's regular counsel, Guercio & Guercio, is paid separately, under its own retainer.)

Locust Valley hired him too. Its board retained him as special counsel in October 2025, and he filed its copycat bathroom lawsuit — the one that named Massapequa parents as defendants. On November 12, 2025, the Commissioner of Education wrote to Locust Valley that it should have known its policy would be stayed "because they retained the same lawyer as Massapequa."

Holtzman Vogel — the dark-money firm

Holtzman Vogel is a Washington political-law firm, founded by the former chief counsel of the Republican National Committee.

What it does: campaign finance, election law, tax-exempt organizations, government ethics. Federal records show its biggest clients are the Republican national campaign committees and Karl Rove's American Crossroads.

OpenSecrets describes the firm as "known for its work with secretive dark money groups." ProPublica and WNYC called it "the go-to place for conservative dark money groups."

In 2020, The Daily Beast reported from court records, firm founder Jill Holtzman Vogel advised Kanye West's presidential campaign behind the scenes. The work never appeared in the campaign's federal filings — watchdog groups said it may have been an illegal, undisclosed contribution.

It does not list education law among its practice areas. No school district appears in its client lists. Before Massapequa, its only school-related work was election law for parent groups fighting school boards in Virginia.

On September 9, 2025 — the same night the board adopted the bathroom policy — the board passed a resolution authorizing "its special counsel, Nicholas Rigano and Holtzman Vogel, to commence litigation in Federal and/or State court." Nobody had sued the district over the policy. The board hired the litigators first.

Holtzman Vogel has billed $118,707, on the mascot refiling and the bathroom case, alongside Rigano. On the bathroom case, its invoices are headed by Susan Greene, a partner who joined the firm in 2025 from a law-school professorship — billed at $430 an hour.

While the firm was on the mascot case, the lawyer doing its work was Oliver Roberts. When he left at the start of 2026 and opened his own firm, the mascot case went with him. Holtzman Vogel stayed on the bathroom case.

Oliver Roberts — the AI lawyer

Oliver Roberts is a Massapequa native and Harvard Law graduate who built his career in artificial-intelligence law: co-head of Holtzman Vogel's AI practice group, co-director of Washington University's Law AI Collaborative, founder of an AI-training company, and editor-in-chief of "AI and the Law."

His own firm offers three services: business strategy, contracts, and AI compliance. No education law. His best-known courtroom win is a tax case against the IRS.

After the first mascot dismissal, he wrote to Education Secretary Linda McMahon, asking the federal government to investigate New York, block the mascot policy, and withhold funding. He appeared on Fox News three times to discuss the case.

At the start of 2026 he left Holtzman Vogel and opened The Roberts Legal Firm — which has billed $38,107 on the mascot appeal since.

The pro bono story

The public was told Oliver Roberts was working pro bono.

News coverage introduced him as the hometown lawyer working on the case for free. Roberts did mark some early work, and some line items, as pro bono. The rest was billed.

The district's own invoices tell the story. His time through Holtzman Vogel was billed at $390 an hour — one June 2025 invoice bills his work entry after entry at that rate. Holtzman Vogel billed $118,707 in total. Roberts's own firm billed $38,107 more in 2026 alone. Rigano billed at $350 an hour throughout.

In December 2025, Board President Kerry Wachter went further: she told the public that Rigano and Holtzman Vogel were handling the case pro bono.

Asked about it in May 2026, Trustee Danielle Ocuto said it plainly: "No, we never had free lawyers."

The pattern

A bankruptcy lawyer runs the civil-rights cases. A campaign-finance firm helps run the bathroom case. An AI lawyer fronts the mascot fight.

That is not how school districts hire lawyers. Districts hire for expertise in the case. This board hired for the politics of the fight.

The other districts in these cases used their regular school lawyers. They lost, or settled, and went back to running schools.

Massapequa's taxpayers got the bill: $345,822 in invoices — on top of what the district already pays its regular counsel.