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In text messages, coordinators of Ron DeSantis’ migrant flights to Martha’s Vineyard reveled in plotting surprise political stunt

Venezuelan migrants board a bus on a ferry from Martha's Vineyard to Woods Hole on Sept. 16. The group was transported to Joint Base Cape Cod in Buzzards Bay.Carlin Stiehl for The Boston Globe

The text messages were punctuated with exclamation points, thumbs-up emojis, and smiley faces. “Yahtzee!” crowed one missive, after a key goal was attained.

Weeks before 49 migrants were flown to Martha’s Vineyard in a surprise event that thrust Massachusetts into the national spotlight, Florida officials and executives with a Florida-based plane company were on the ground in Texas gleefully exchanging plans to send unassuming migrants to blue states, according to documents obtained by the Globe.

Beyond emojis, Florida Governor Ron DeSantis’ public safety czar Larry Keefe and others made plans to celebrate their work with “some wine at dinner,” according to the documents, released this week as part of a public records request.


Florida’s $12 million state-funded migrant relocation program has since become the center of a criminal probe, and some of the migrants sued DeSantis and others involved in the relocation. They allege Florida officials and others defrauded them by making false claims about where they were going and the benefits — including money and jobs — they would receive upon arrival.

While DeSantis immediately took credit for sending the migrants to the Vineyard on Sept. 14, the documents provide new, granular details about the involvement of other high-level officials and the time they spent in Texas before the September flights.

Keefe and businessman James Montgomerie, who owns the company Florida hired to fly the migrants from San Antonio, conferred about travel logistics and communications with the Florida Department of Transportation. They messaged using Signal, an encrypted messaging app, according to the documents.

Keefe was also often in contact with Perla Huerta, a former US Army counterintelligence specialist who migrants said recruited and enticed them to board the flights.

Meanwhile, a separate series of texts revealed the administration of Texas Governor Greg Abbott was privy to the plan. James Uthmeier, the chief of staff for DeSantis, and Luis Saenz, who served in that role for Abbott, exchanged messages sharing Keefe’s contact information. Those texts were obtained from Texas by the Florida Center for Government Accountability and provided to the Globe.


Advisers of Florida Governor Ron DeSantis and the office of Texas Governor Greg Abbott were both looped in on the progress of the transfer of migrants from San Antonio to Martha's Vineyard.OFFICE OF THE TEXAS GOVERNOR/NYT

Uthmeier wrote that Keefe was asked to be the point of contact for the operation in Texas, and can loop in other parties “as needed.”

“He serves as one of [DeSantis’] senior advisors for public safety. He’s a former US Atty under Trump,” Uthmeier told Saenz. “Trustworthy and effective.”

Neither DeSantis, Huerta, Keefe, nor Montgomerie responded to requests for comment.

The texts among Florida officials and their agents were mostly used to share mundane details like booking hotel rooms and rental cars. But they sometimes had an air of excitement, where DeSantis officials and others discussed updates on their travels to Texas and efforts to recruit migrants in August.

Keefe was heavily involved in coordinating the effort, the documents show. In the texts, he shared bits of information or news clips with Huerta and others in the chat, like a New York Post article with the headline “How selfies fuel rise in illegal migrants.”

“Maybe we should encourage selfies,” Huerta responded.

A few weeks later, Keefe shared an El Paso Times article about Abbott’s program to bus migrants to cities like Chicago, New York City, and Washington, D.C.

“I’m sure it won’t be long before other places jump on board,” Huerta responded.

In the messages, Huerta asked for advice on where to find migrants, and she showed Keefe screen shots of Google searches she had made. One asked: “What states are immigrants going to?” The second posed: “Which US state has the least amount of immigrants?”


As she searched for migrants to recruit in San Antonio, she detailed to Keefe all the places she had looked: churches, a transportation office, a Stripes convenience store parking lot.

On Saturday, Sept. 10, Montgomerie, who owns the transportation company Vertol Systems, told Keefe that they had secured 34 migrants and “will be at 50 by Tuesday, no problem.” He said he believed they could arrange another flight to President Biden’s home state, Delaware, for the following week. Other records obtained by the Globe showed that Vertol pitched the Florida Department of Transportation additional migrant flights to Delaware and Illinois, where former President Barack Obama spent much of his adulthood.

“The network has grown exponentially!” Montgomerie told Keefe, according to the documents. “We believe we could probably generate another 50 inside 48 hours.”

James Montgomerie

Sept. 10, 2022, 7:03 PM

  1. We are at 34 tonight confirmed on the manifest, will be at 50 by Tuesday no problem

  2. Excellent
  3. Sept. 11, 2022, 2:33 PM

    Larry Keefe

  4. We are 50 today 👍
  5. Congratulations. Great work

  6. The network has grown exponentially!
    We believe we could probably generate another 50 inside 48 hours

The Miami Herald has reported that Keefe had represented Vertol Systems in a dozen lawsuits between 2010 and 2017, when he was a private attorney.

Two days before the Vineyard flights, Huerta shared with Keefe that they had secured enough migrants to fill the two planes: “Yahtzee!! We’re full.”

2 people

Sept. 12, 2022, 6:20 PM

  1. Yahtzee!!

    We're full
  2. Perla Huerta

  3. Excellent!
  4. Larry Keefe

On Sep. 14, the day the migrants were flown from San Antonio to Massachusetts, Keefe texted a contact he dubbed “Kiwi” the cellphone number for Dave Abrams, an adviser to DeSantis’ political operation.


Perla Huerta

Sept. 14, 2022, 4:21 PM

  1. Victory Arms For you!!!! Thank you for this opportunity and support.

  2. Thank you for all, Perla !!! Let's drive on !!! Salute to you. Larry
  3. Larry Keefe

The day the migrants, confused and lost, landed in Massachusetts, Huerta wrote to Keefe: “Victory Arms For you!!!! Thank you for this opportunity and support.”

Keefe responded: “Thank you for all, Perla !!! Let’s drive on !!!”

Read our previous coverage on the migrants sent to Martha’s Vineyard:

Samantha J. Gross can be reached at Follow her @samanthajgross.