City Attorney Rejected Small Settlement, Benefited From Prolonged Lawsuit

OCEAN SPRINGS, MS – A recent public records request revealed that the Ocean Springs Board of Aldermen quietly gave away their authority to City Attorney Robert Wilkinson’s private law firm — a move that may have resulted in significant legal fees paid to Wilkinson and his firm.

Decisions that should have been made by elected officials in public meetings were instead made behind closed doors by lawyers with a financial stake in the outcome.

Now, a quiet settlement in a free speech lawsuit has opened the door to a bigger question: How many times over the past 20 years has Wilkinson’s firm made legal decisions, collected legal fees, and cut settlement deals — all without the Board’s approval or the public’s knowledge?

A Federal Lawsuit That Didn’t Have To Be

In 2023, Ocean Springs was one of many Coast cities visited by Jeff Gray, a First Amendment auditor who travels the country testing free speech rights. Gray stood on the front lawn of City Hall holding a handwritten sign that read, “God Bless the Homeless Vets.”

Gray’s audits consist of peaceful demonstrations in public areas to evaluate whether local authorities uphold citizens’ constitutional rights to free speech and assembly. In Ocean Springs, however, Gray’s display sparked a hostile encounter with local police, who ultimately cited him for trespassing — despite his presence on public property.

Within minutes, Ocean Springs city officials called 911 to have Gray removed. The encounter with police, which was documented on video and published to Gray’s YouTube channel, went viral and caused uproar throughout the nation.

A federal lawsuit followed, but not before Gray tried to resolve the issue with city officials.

Gray initially proposed a simple resolution: a modest $1,791 donation to a homeless veterans charity and a few procedural reforms to safeguard free speech rights. Rather than accept, the city chose to engage in a costly legal fight — escalating a minor dispute into a federal lawsuit and drawing attention to a possible conflict of interest within its legal process.

The City Clerk’s office has confirmed the decision to decline Gray’s proposal was made without a vote by the Board of Aldermen.

Unilateral Decisions by City Attorney

City Attorney Robert Wilkinson serves as the city’s legal advisor through a contract arrangement — but when Ocean Springs is sued, it’s his private firm, Wilkinson, Williams, Bosio & Sessoms, that often gets hired to defend it. This setup allows Wilkinson to profit from litigation he is ultimately tasked with helping the city avoid.

Unlike cities with in-house legal departments, Ocean Springs outsources its legal work to Wilkinson’s firm. He handles routine matters such as drafting contracts and reviewing board actions. But when lawsuits arise, the Mississippi Municipal Service Company (MMSC) — the city’s litigation insurer — selects and hires outside counsel to represent the city in court.

Public records reveal that in nearly every recent case, MMSC has appointed Wilkinson’s own firm for the job. The Jeff Gray lawsuit was no different. Once the settlement offer was declined, MMSC once again hired Wilkinson’s private firm to handle the incoming litigation. Robert Wilkinson served as lead counsel.

After a year of motions, depositions, and negotiations, the Jeff Gray lawsuit was ultimately settled. However, the terms and process behind that settlement remain shrouded in secrecy—and possibly marred by unlawful conduct on the part of City Attorney Robert Wilkinson.

From the outset, Wilkinson exercised near-total control over the city’s handling of the case. He was the one who rejected Gray’s original offer to resolve the dispute amicably through a modest donation to a veterans charity and a few policy adjustments. Instead of presenting the offer to the Board of Aldermen, Wilkinson chose to escalate the matter into an expensive legal battle, racking up months of litigation costs and exposing the city to mounting liability.

Then, just days before his tenure as city attorney came to an end, Wilkinson made yet another unilateral decision: he settled the case. Under Mississippi law, all final actions involving public funds — particularly settlements — must be approved in a public vote by the Board of Aldermen. But in this case, there was no vote, no public discussion, and no official record of authorization. The city later confirmed they were never informed, let alone consulted.

The entire matter was handled behind closed doors, with Wilkinson acting as both legal advisor and final decision-maker — despite clear statutory requirements to the contrary.

The Secret Settlement

Gray told GC Wire the case had been resolved and that final agreements included a non-disclosure clause preventing him from revealing details. However, Mississippi law is clear: a municipality cannot conceal the use of public funds through private agreements. Under the Mississippi Public Records Act, all records involving the expenditure of public money — including settlement agreements — are subject to disclosure, regardless of any confidentiality provisions imposed by one or both parties.

To verify the details, GC Wire submitted a formal public records request seeking a copy of the executed settlement agreement between Gray and the City of Ocean Springs. In response, the City Clerk’s office denied the request, offering no lawful exemption and no explanation for withholding a document that is, by law, a public record.

That denial directly violates the Mississippi Public Records Act, which requires the disclosure of all finalized contracts involving public funds.

The Ethics Commission has repeatedly held that even when a settlement agreement includes a confidentiality clause, the document itself — and particularly the payment amount — cannot be shielded from the public. Government agencies are not allowed to contract around transparency, and any attempt to do so is both legally unenforceable and a violation of the public’s right to know how their tax dollars are being spent.

While the settlement was paid through the city’s municipal insurance fund, that does not absolve Ocean Springs of its legal responsibilities. The City of Ocean Springs remained the named defendant in the case, and under state law, any final action — including the decision to settle — required a formal vote by the Board of Aldermen. No such vote occurred.

Moreover, the source of the funds does not change the fact that public money was used to resolve a lawsuit involving official conduct. The Mississippi Public Records Act does not carve out exceptions for insurance payouts; the amount paid on the city’s behalf must still be disclosed. The public has a right to know not only how much was spent, but also who made the decision — and whether it was done lawfully.

The Bigger Question

The Jeff Gray case raises a larger question that Ocean Springs residents deserve to ask: how many times over the past two decades has this happened before?

How often has a simple, inexpensive solution been cast aside in favor of prolonged litigation — enriching the same attorney who advised the city to reject the settlement in the first place?

And how many of those decisions were made without a single vote from the elected officials who are supposed to represent the public?

The handling of the Gray case isn’t just a one-off lapse — it may be part of a long-standing pattern where transparency is bypassed, laws are ignored, and power is quietly concentrated in the hands of a single unelected advisor.

Ocean Springs ends its contract with Wilkinson and his firm on June 30, the same day a new Board and Mayor are sworn in.