From confidential deals to curious real estate transactions, the politically connected developer’s shadow looms over the city’s government.
OCEAN SPRINGS, MS – Joe Cloyd was lobbying legislators in Jackson with Ocean Springs Mayor Kenny Holloway when he got the good news. Mr. Cloyd found out he would be getting $6 from every paid traffic citation under the city’s new Securix camera program.
But it was a secret.
The contract Cloyd signed with the company in 2022 had a strict privacy clause. Nobody was to know. Ever.
And that tracks, given the fact that Cloyd was also a public official at the time, serving as the President of the Ocean Springs School District Board of Trustees – a position he was unanimously appointed to by the Board of Aldermen.
Mississippi law prohibits public officials from profiting off city contracts. Also, anyone lobbying legislators is required to register with the Secretary of State’s office. Despite years of lobbyist activity for the city, state records show Cloyd never did.
A Secret Contract with a Very Public Guy
Mr. Cloyd is a politically connected developer, hotel owner, and a behind-the-scenes operator at nearly every level of Ocean Springs government. He is sometimes referred to as “the eighth alderman.” Cloyd is an owner of The Roost and The Hemingway on Washington Avenue, two of the city’s most prominent boutique hotels.
One of the many companies owned by Cloyd purchased Holloway’s family home just prior to him becoming mayor. Throughout his tenure, Holloway has resided in a different home owned by a Cloyd company.
Securix brought Cloyd in under the pressure of Josh Gregory, who is partners with Cloyd in Frontier Gulf Coast, a political consulting firm spun off from Frontier Strategies — the same operations that ran Holloway’s campaigns in both 2021 and 2025.
Cloyd was not added to the team to help secure new municipal clients. Securix had already closed the Ocean Springs deal nearly a year prior. He was added as a fixer, specifically to smooth wrinkles that may arise from the Securix contract with the city.
“He’s going to give us insurance in Ocean Springs if things get rough after the citations hit,” Gregory wrote about Cloyd in a 2022 email to Securix management.
“He ran Mayor Holloway’s runoff and has been active in most of the council races. Jokingly referred to as the ‘8th councilman.’ Current lobbyist for Ocean Springs and is very involved with Jackson County as well,” Gregory added.
Cloyd sent back the signed contract on March 10, 2022. “Thanks for the opportunity to work together,” he wrote along with the attachment. “I have been in Jackson with Mayor Holloway for the past 2 days.”
The contract, recently acquired by GC Wire, stated Cloyd would get $6 per paid traffic citation, to begin after an initial 6,000 citations were paid in Ocean Springs. Embedded in the document was an iron clad secrecy clause, stating, “The parties further agree to keep confidential the existence of this AGREEMENT and also that they are communicating with the other party.”
Ethics Dilemma
Mississippi law is clear: public officials cannot use their position to benefit financially from government contracts, directly or indirectly, without formal disclosure and clearance through the state’s Ethics Commission.
As school board president, Cloyd was a public servant under Mississippi Code § 25-4-103. That designation comes with legal responsibilities — including a prohibition on any undisclosed financial interest in city contracts, especially when the official might influence, benefit from, or have access to decisions surrounding that contract.
And while the school board and Board of Aldermen are separate entities, Ocean Springs functions as one political ecosystem. School leaders, city officials, and developers frequently collaborate on funding initiatives, joint-use projects, and infrastructure planning. The potential for cross-influence is not hypothetical — it’s built into the system.
In addition to his business interests, Cloyd has been actively lobbying for the city and assisting in grant applications since the beginning of Holloway’s term. He was – and still is – clearly in a place of influence with city leaders.
At the very least, Cloyd was ethically obligated to disclose his financial interest in a city law enforcement program. There’s no evidence he ever did, nor was he contractually allowed to.
He Wasn’t the Only One Cashing In
Cloyd wasn’t the only public official benefiting from the Securix deal in Ocean Springs. City Attorney Robert Wilkinson and Police Chief Mark Dunston also had undisclosed financial ties to the program. Both played key roles in enabling its implementation – and molding it to illegally bypass the court system.
Wilkinson, the city’s top legal advisor, was deeply involved in shaping the Securix arrangement, despite claiming he had recused himself from all matters related to the program. Public records and internal emails later revealed that Wilkinson had a personal financial stake in the outcome, and continued steering legal decisions behind the scenes long after his supposed recusal.
Police Chief Mark Dunston was also connected. In addition to helping launch the program inside the police department, Dunston was later revealed to be on the payroll of Securix itself — a fact that neither he nor the city disclosed to the public while the program was operational.
In 2023, the Securix program in Ocean Springs collapsed under the weight of unethical city practices and growing anger from residents.
Another Traffic Scheme, Another Cloyd Connection
After the collapse of Securix, Wilkinson and Dunston didn’t walk away from the traffic ticket business — they just rebranded it. In late 2023, the pair quietly launched a new enforcement company called Intellisafe, aiming to replicate the same automated citation model that had sparked outrage across Ocean Springs.
The new “Intellisafe” company, which is still up and running with contracts in Moss Point and Hattiesburg, also bypasses the court system. This time, holding faux hearings, designed to mimic official proceedings, in the lobbies of government buildings – actions that have led to multiple lawsuits initiated by residents.
And just like before, Joe Cloyd was close by. Literally.
Intellisafe’s registered headquarters is 929 Washington Avenue — the location of Cloyd’s Hemingway Hotel. It’s the same address used on incorporation documents and official filings. It’s also the same building where the company that owns Mayor Holloway’s current rental is registered.
A History of Influence
Cloyd’s presence and influence in Ocean Springs government is not new. For example, back in 2018, his voice held heavy weight in city infrastructure decisions.
On May 18th of that year, Cloyd appeared at a Board of Aldermen meeting to oppose a FEMA-funded plan to elevate a sewage lift station near his East Beach property. The plan was to raise multiple stations across Ocean Springs.
City engineers warned that failing to elevate the stations could result in raw sewage flooding the streets during a power outage. Alderman John Gill and others were adamant about listening to the experts.
But then Joe Cloyd raised his hand to tell Board members he wants the one by his house to remain like it is. He said elevating the stations would be an unwelcomed scenic change for him.
The Board voted unanimously to leave that one alone. That’s some pretty strong influence.
Coincidentally, this was the same meeting the aldermen voted to approve Securix behind closed doors.
Mr. Cloyd did not respond to a request for comment prior to publication. This article will be updated if a response is received.
Very interesting article. Thank you for your service to our country in Somalia and Bosnia.
Seems like under every rock is a corrupt individual……