Josh Gregory hosted a fundraiser for Attorney General Lynn Fitch at his home while simultaneously awaiting an AG opinion on the Securix program. In a private email, he promised a campaign contribution ‘if they ever finish the damn opinion.’ Thousands in donations followed.
OCEAN SPRINGS, MS (GC Wire) — While Mississippi Attorney General Lynn Fitch’s office was considering a legal opinion that could clear the way for a controversial private traffic-ticketing operation, political consultant Josh Gregory, who had a financial interest in the operation, sent an email that is just now being made public, and it is raising eyebrows.
The newly obtained August 6, 2022 email reveals Gregory’s plan to tell Fitch’s financial team that someone from the Securix camp would contribute money to her campaign “if they ever finish the damn opinion so we can get kicked off.”
In the same email, Gregory acknowledged that making a donation while the opinion was pending would be inappropriate. But rather than abandon the contribution, he hosted the fundraiser and also proposed promising money from his group would come once they acquired her opinion.
Copied on the email was Ocean Springs City Attorney Robert Wilkinson, who was also working with the Securix team to launch the controversial program. Wilkinson was also the very person who had requested the pending legal opinion from the Attorney General’s Office.
Wilkinson would later claim that Fitch’s office provided a favorable opinion verbally to him, rather than through the more standard procedure of publishing the opinion publicly on the state’s searchable website.
His private law firm subsequently contributed $5,000 to Fitch’s campaign.
The Email
On August 6, 2022, Gregory emailed Securix CEO Jonathan Miller about an August 25 fundraiser at Gregory’s home. The subject line read “Fitch.”
Wilkinson was copied on the correspondence.
Gregory wrote:
“JM, plan on being at this event at my house on the 25. I’m going to tell the fundraiser it wouldn’t be appropriate for you to write a check while an opinion is pending but you will if they ever finish the damn opinion so we can get kicked off.”
He added:
“I’m going to also get the collections guys to write a check for this event as well.”
The email included an attachment of the Fitch fundraiser dinner invitation. Miller told GC Wire the “collection guys” referred to the company collecting the fines from Ocean Springs motorists.
Gregory was not merely discussing routine political giving. He planned to tell Fitch’s fundraising team that a campaign contribution would follow once her office completed its opinion, even as that opinion remained pending.
Miller did not ultimately make the promised contribution, but contributions subsequently came from another member of the Securix team: Ocean Springs City Attorney Robert Wilkinson, whose private law firm contributed $5,000 to Fitch’s campaign.
The Financial Interests Behind the Securix Team
The relationships among Gregory, Wilkinson, and Miller extended well beyond political consulting and legal representation.
When Securix launched its uninsured-motorist enforcement program in Ocean Springs, Gregory’s Frontier Strategies firm was contractually entitled to receive approximately $36 for every paid citation, according to Securix CEO Jonathan Miller.
That arrangement gave Gregory a direct financial interest in the volume of citations generated by the program.
Meanwhile, Wilkinson, while serving as Ocean Springs City Attorney, was working with Securix to secure additional municipal contracts, often touting to prospective cities the progress he was having in Ocean Springs.
The business relationships were further cemented with the creation of QJR LLC in 2023, a company whose name represented the first names of its three principals: Quinton Dickerson, Josh Gregory, and Robert Wilkinson.
Dickerson and Gregory were partners in the Frontier Strategies consulting firm, while Wilkinson was both a private attorney working with Securix while still a public official in Ocean Springs.
QJR immediately entered into a 50-50 partnership with Securix to establish Securix Mississippi LLC, giving the three QJR principals an ownership interest in the company positioned to expand the ticketing operation across Mississippi.
The financial arrangements are significant to the August 2022 fundraising email.
Gregory was not simply organizing a political event for a candidate he supported when he wrote the email. He had a financial stake in Securix’s ticketing operations, as well as one in receiving a favorable opinion by the Attorney General.
The three men were working toward the same business objective when Gregory proposed telling Fitch’s fundraiser that a campaign contribution would follow “if they ever finish the damn opinion.”
Wilkinson’s Wishy-Washy Accounts of His Securix Involvement
Robert Wilkinson has provided conflicting accounts of when his involvement with Securix began.
In June 2025, the Sun Herald reported that Wilkinson claimed he first met Securix CEO Jonathan Miller around May 2021, but did not establish a business relationship until six to ten months after Ocean Springs signed its contract, which was May of 2021.
However, internal Securix documents obtained by GC Wire identify Wilkinson in a proposed financial agreement dating to March 2021. A March 2022 email also shows Wilkinson personally renegotiating a consulting agreement with Securix and referencing work performed over the preceding 12 months — contradicting the timeline he provided to the Sun Herald.
Also in 2025, Wilkinson gave another account of his involvement with the company. This time it was to the Mississippi State Bar.
In an April 2025 letter defending a Bar complaint, Wilkinson told the agency he first learned of the existence of Securix in 2022, while in the same letter confusingly mentions emails he sent regarding Securix in 2021.
$12,700 in Campaign Contributions During Securix Window
As the Securix team was being assembled in early 2021, firms associated with Josh Gregory and Robert Wilkinson were already contributing to Attorney General Lynn Fitch’s campaign.
Campaign-finance records show that Wilkinson’s former law firm, Dogan & Wilkinson, contributed $6,500 in 2021, while Gregory’s Frontier Strategies contributed another $1,200. The donations occurred both before and after Ocean Springs signed its Securix contract that May.
Following Gregory’s August 2022 fundraising email, Wilkinson’s later law firm, Wilkinson, Williams, Bosio & Sessoms, contributed another $5,000 — $2,500 in September 2023 and $2,500 in August 2024.
In all, firms connected to Gregory and Wilkinson contributed $12,700 to Fitch’s campaign between 2021 and 2024.
The final $2,500 contribution came just 14 days before the Mississippi Department of Public Safety ordered Securix’s access to the state’s insurance database terminated.
GC Wire has been unable to locate any contributions to Fitch from the group after the Securix program was shut down.
The contributions do not establish that Fitch took any action in exchange for campaign money, nor do they indicate the Attorney General was notified about the offer to contribute money following the rendering of her opinion.
Securix CEO Jonathan Miller eventually became a whistleblower, providing oversight agencies and this reporter with thousands of documents that he claims show Gregory and Wilkinson “bastardized” his software company and failed to follow state and federal laws.
Miller told GC Wire reports of illegal activity were “sent twice to the AG’s appointed ‘fraud guy’ and never had the courtesy of a response.”
GC Wire has reported extensively on those alleged actions, as well as information obtained through our own investigations.
We are publishing the unedited August 6, 2022 email so readers can examine Gregory’s words and the circumstances surrounding them for themselves:
