The Gulf Shores private investigator indicted this month for allegedly impersonating a law enforcement officer once played a central role in an elaborate undercover operation aimed at Fairhope public officials — a months-long ruse in which she and a partner posed as an Atlanta couple looking for a home on the Eastern Shore, according to sworn court testimony.
Court records from a 2022 federal lawsuit show Tobi Lynn Libbra was identified as part of a private investigative team allegedly hired by Baldwin County developer 68 Ventures, posing as a couple from Atlanta looking to relocate. The operation, detailed in a sworn declaration by Fairhope Planning Commissioner Hollie MacKellar, was staked out over multiple months and involved fake identities, handcrafted backstories and spoofed Facebook profiles.
Libbra was indicted by a Mobile County grand jury earlier this month on two criminal counts brought by the Mobile County District Attorney’s Office, which alleges she pretended to be a state investigator in order to secure an interview with a witness in the DA’s fraud lawsuit against South Alabama Medical & Rehab. A recording of that interview was played in open court on July 17 by the injury clinic’s attorneys. She was arrested Monday, Aug. 24, after prosecutors secured the indictment.
Records show this is not the first public controversy involving Libbra and her affiliated firms.
‘The Cuttinghams’
In a 2024 sworn affidavit filed in the federal case, MacKellar claims she and two other Fairhope officials were secretly recorded by Libbra and one of her partners during an operation MacKellar says was intended to elicit inflammatory statements that 68 Ventures could use in its ongoing litigation against the city over rejected subdivision plans.
According to MacKellar’s affidavit, investigator Ketrick Kelley contacted her in June 2022 pretending to be a man named “Tyler Cuttingham,” while Libbra allegedly played his wife, “Olivia.”
“Unbeknownst to me, the Cuttinghams were impostors that were hired by 68V to secretly record me and attempt to entrap me into making statements against Nathan Cox, 68V, and the Gables at Lawrence project,” the affidavit states. “Also, unbeknownst to me, the people pretending to be the Cuttinghams secretly recorded every meeting and telephone conversation we had without my knowledge or permission, and under false pretenses.”
MacKellar said the couple fabricated a house-hunting backstory and asked for her help finding a home in Fairhope. She met Kelley in person on June 28, 2022, while he was undercover, and showed him two houses — the start of a relationship that continued for months through dozens of follow-up meetings, calls, texts and emails. She testified that she dedicated more than 20 hours to working with the Cuttinghams.
A story that grew more personal
According to MacKellar’s testimony, the fictional couple’s backstory grew increasingly intimate as the operation stretched on.
“They told me that Olivia Cuttingham’s mother had fallen, was in Thomas Hospital, and was in poor health,” she stated. “Later, they told me that Olivia’s mother was seeing a doctor in New Orleans, and a few months later they told me that her mother had passed away. I prayed for the Cuttinghams particularly on the news that Olivia’s mother passed away.”
By October 2022, MacKellar said, Libbra had joined the operation in person: she, Kelley and Libbra met for lunch at Dragonfly in Fairhope before returning to MacKellar’s real estate office to review additional listings. Libbra added her own details to the couple’s backstory, MacKellar said, including a claim that she had been assaulted in Atlanta and was especially concerned about crime when considering where to live.
MacKellar said she later learned nearly every element of the relationship had been manufactured.
“I have since learned that almost all of what they told me was a lie, including their made-up cover story involving a pretend family and false reasons for contacting me,” she stated.
Burner phones and a phony Facebook
MacKellar alleged the investigators used burner phones, fake email addresses and a phony Facebook account to maintain their identities. She also claimed Kelley met with Fairhope Planning Director Hunter Simmons and Planning Commissioner Rebecca Bryant under false pretenses and secretly recorded them as well.
She said the conversations were steered toward crime, class and 68 Ventures’ proposed Gables at Lawrence development, in an apparent attempt to prod her into making negative statements about low-income housing and company founder Nathan Cox. “Kelley repeatedly asked me about unsafe areas around town, and repeatedly stated that he was trying to avoid areas with ‘transients’ and avoiding areas of town with ‘low rent,’” she stated. At one point, she said, Kelley brought up the Gables project directly, asking “what kind of people are living in those houses.”
MacKellar maintained her vote against the Gables project was based on traffic and drainage concerns, and she denied that her opposition was motivated by the prospect of apartments or lower-income housing. She said the experience changed her view of Cox and 68 Ventures, noting she had previously recommended homes built by Cox’s former company, Truland Homes — and had even presented some of them to Kelley and Libbra during their operation.
“I did not think he would stoop to the level of hiring someone to secretly record and harass volunteer Commissioners, deceptively trying to get us to say something that was not true,” MacKellar stated.
The litigation behind the operation
68V BTR Holdings sued Fairhope in October 2022 after the Planning Commission rejected the Skyline and Gables projects, alleging the denials were arbitrary, capricious and violated due process. The case has been stalled on appeal since December 2025 pending a decision by the Alabama Supreme Court.
Kelley and Libbra are both licensed private investigators and partners in Kelley’s firm, ketWork Investigations, and Libbra’s company, 4:59 Consulting. Kelley, according to his online resume, is a retired FBI special agent and former Mobile police officer with more than three decades of investigative experience, including an assignment to the FBI’s local white-collar crime unit. He was previously reported to have been assigned to a drug investigation into Orange Beach fitness trainer Danny Williams — a case that was used to launch a probe into local public officials.
Neither Kelley nor Libbra has been charged in connection with the Fairhope operation, and 68 Ventures has not publicly responded to the allegations in MacKellar’s affidavit. The affidavit was filed as evidence by Fairhope’s attorneys in the federal case, where its claims remain contested.
From the sting to the indictment
Libbra’s recent legal trouble is separate. The Mobile County DA secured an indictment alleging she violated state law by posing as a state investigator to secure a recorded interview with one of the state’s witnesses in October 2025 in the civil fraud case against South Alabama Medical & Rehab — the alleged “claim-jacking” operation the DA says funneled crash reports through telemarketing, treatment and legal referrals. The clinic, which has ties to Texas chiropractor Michael Kent Plambeck, was closed prior to a preliminary injunction ordering it to cease operations in the case. Plambeck and his companies were previously sued under RICO in Ohio in 2008 for a nearly identical operation and found liable for millions of dollars.
For Fairhope, the newly public details add an unusual chapter to a running dispute between the city and one of Baldwin County’s most prolific developers — and raise questions, at least for the officials who spent months unknowingly hosting two fictitious house hunters, about how far private investigators will go when a developer’s project is on the line.