DeSantis aide used private email in talks with ex-client over migrant flights contract

Larry Keefe, the governor’s public safety czar, used a private Gmail address that displayed his name as “Clarice Starling.”
Gov. Ron DeSantis' public safety czar, Larry Keefe, was previously the U.S. attorney for the Northern District of Florida.
Gov. Ron DeSantis' public safety czar, Larry Keefe, was previously the U.S. attorney for the Northern District of Florida. [ U.S. Department of Justice ]
Published Dec. 27, 2022|Updated Dec. 28, 2022

A top aide to Gov. Ron DeSantis used a private email address with the alias “Clarice Starling” — a reference to the Hannibal Lecter serial killer novels — to help his former client win a state contract to operate Florida’s controversial migrant flight program, recently released public records show.

The records suggest that Larry Keefe, DeSantis’ public safety czar, wrote some of the language that the private contractor, Vertol Systems Co., used in its bid proposal to fly migrants from Texas to Democratic states.

Keefe, a former U.S. attorney under the Trump administration, represented Vertol for many years in private practice. DeSantis appointed him last year as a top adviser with a portfolio that included combating illegal immigration.

Related: Top DeSantis aides were deeply involved in migrant flights

The emails between Keefe and his former client, Vertol CEO James Montgomerie, first reported by NBC6, show a close relationship that continued after Keefe entered government service. It was a relationship that helped Vertol land a lucrative taxpayer contract, which Keefe discussed without using his standard, state-issued email account.

“This is the email channel to use,” Keefe wrote to Montgomerie on Aug. 26, as Vertol, an aviation company based in Destin, was preparing to bid for the state’s migrant flight program.

The email account was a private Gmail address that displayed Keefe’s name as “Clarice Starling,” the FBI trainee and heroine from the serial-killer thriller book and movie “The Silence of the Lambs.” The account also included the phrase “Heat 19,” which Keefe said was a call sign given to him during his time in private practice by a former U.S. Air Force Special Operations commander.

Four days after that initial message, Keefe sent Montgomerie eight paragraphs of language that the Vertol CEO would include almost verbatim in his official proposal for the migrant flight program. The Florida Department of Transportation approved Vertol’s proposal soon after, and the first flights happened a little more than a week later.

Keefe and Montgomerie exchanged dozens of emails and text messages — some on the encrypted messaging app Signal — in the run-up to the contract being approved.

DeSantis’ office did not answer questions about why Keefe was using a private email address. Keefe and Montgomerie did not immediately respond to requests for comment.

The new emails were released by DeSantis’ office just before Christmas.

The records became public only after wrangling between the governor’s office and the Florida Center for Government Accountability, a nonprofit that has sued the state over delays in releasing public records about its migrant flight program.

Related: Watchdog group wants DeSantis held in contempt over withholding public records

The program has so far seen Florida pay Vertol at least $1.5 million to fly 49 mainly Venezuelan migrants from San Antonio, Texas, to Martha’s Vineyard, a Massachusetts island, on Sept. 14, as well as for planning flights to Delaware and Illinois that have yet to happen. While DeSantis has defended the flights as an attempt to draw attention to the border crisis, the taxpayer-funded program has led to several lawsuits, including from migrants who say they were tricked into getting on the planes, and a criminal investigation by the Bexar County sheriff in Texas.

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The migrant flight program was designed to remove “unauthorized aliens” from Florida. But critics, including Florida Democrats and immigration advocacy groups, have pointed out that the migrants had legal status in the United States and were found in Texas, not Florida. Internal documents show Vertol and the state referring to the program as a “humanitarian operation.”

DeSantis handily won reelection this year and is expected to be among the front-runners for the Republican presidential nomination in 2024. The migrant flights proved popular with his GOP base.

Several attendees at the governor’s preelection rallies wore “DeSantis Airlines” T-shirts.

‘Antithesis of open government’

Although state officials like Keefe are allowed to conduct public business via private email, doing so raises questions of transparency, according to Michael Barfield, director of public access for the Florida Center for Government Accountability.

“Our open government laws were designed to prevent backroom deals and keep the public informed. This is the antithesis of open government. Using encrypted apps and military lingo, it doesn’t square with doing things in the sunshine,” Barfield said in an interview. “Worse, both Mr. Keefe and Mr. Montgomerie knew what they were doing. They are very well versed in the public records laws. Communicating in this way sure makes it more difficult for the average citizen ... to uncover what was really going on behind the scenes.”

The emails were not originally produced in response to public records requests. After the Florida Center for Government Accountability suggested that the state was withholding some records, Keefe remembered that he might have used the “Clarice Starling/Heat 19″ email account to discuss the migrant flight program, according to the state’s Office of Open Government.

That led the state to discover the communications between Keefe and Montgomerie, including the email where Keefe appears to draft Vertol’s bid.

“Who is Mr. Keefe working for?” Barfield said. “The state of Florida or the contractor or both?”

The emails also suggest that Montgomerie lied under oath when being deposed in the Florida Center for Government Accountability’s lawsuit, according to a motion the nonprofit filed in court.

During sworn testimony last month, Montgomerie was asked about a “draft” he mentioned in a Sept. 1 Signal message to Keefe. Montgomerie replied that he was talking about a consent form to be filled out by migrants. But the recently released emails show he was actually discussing the draft for Vertol’s bid, according to the Florida Center for Government Accountability.

In its motion, the nonprofit is asking a judge to allow it to question Montgomerie again.

Miami Herald staff writers Mary Ellen Klas and Ana Ceballos contributed to this report.