When Gov. Ron DeSantis’ administration needed a company it could trust to implement a controversial interstate immigrant transfer program, it made an unusual choice. Although Destin-based Vertol Systems Company is involved in aviation, its primary business is training pilots for the military and supplying helicopters around the world. But the company was familiar with a key member of the DeSantis administration: Larry Keefe, the state’s “public safety czar” responsible for carrying out the governor’s anti-immigration programs. The company also has a private jet that flew from Florida to San Antonio a week before charter flights took 48 migrants to Martha’s Vineyard. Before DeSantis hired Keefe and before he was appointed U.S. Attorney for the Northern District of Florida by then-President Donald Trump, Keefe represented Vertol Systems in a dozen lawsuits between 2010 and 2017. Keefe has steered the company’s strategy into lawsuits, suing former employees accused of misappropriating funds, contractors suspected of stealing company secrets and a local lawn care company that stepped over a cable attached to one of the company’s helicopters. The state has paid Vertol Systems more than $1.56 million to organize, among other things, last week’s migrant flights from Texas to Martha’s Vineyard, which have sparked outrage, a criminal investigation by a local sheriff and a federal lawsuit by some of the immigrants. So far, Keefe’s ties to Vertol Systems are the best explanation for why the state hired the company. The DeSantis administration has released few details about the secret program, which is being paid for with $12 million in interest earned from federal COVID aid money. State officials did not say how they selected Vertol Systems, whether the state solicited multiple bids for the project as required by the Legislature, or even released the state’s contract with the company. The governor’s office did not respond to requests for comment. READ MORE: DeSantis-linked officials promised to fly immigrants to Delaware — but left them stranded Court documents and other records show the company is active in GOP politics. In addition to Keefe, U.S. Rep. Matt Gaetz, who Keefe hired before Gaetz was elected to Congress, also represented Vertol Systems in two lawsuits in 2010. The company and its owner, James Montgomery, have given $27,000 to Republican politicians and political committees since 2005. Vertol Systems is also a partner in a company called Zeppelin Holdings LLC with Jay Odom, a prominent Okaloosa County developer and close associate of Gaetz. In 2009, Odom was indicted along with Florida House Speaker Ray Sansom and the then-president of Northwest Florida State College, accused of diverting state school construction funds to build a shed for Odom’s business, Destin Jet. The charges were dropped, but in 2013, Odom pleaded guilty to campaign finance violations in a separate case and was sentenced to six months in prison. Zeppelin Holdings LLC owns an eight-seat Cessna Citation jet that flew a similar route to the planes that went to Martha’s Vineyard. Flight tracking data shows that on September 5, the week before the Martha’s Vineyard flights, Zeppelin’s Cessna flew from Destin to Tallahassee, stopped in Tampa, returned to Destin, and then traveled to San Antonio, where it stayed until September 7. Flight records for the same jet from the previous month show no trips to San Antonio. The jet returned to San Antonio again on September 16, two days after completing the flight to Martha’s Vineyard. Tracking data shows the jet stayed at the San Antonio airport for an hour and returned to Destin. Neither Keefe, Odom nor Vertol Systems responded to questions about whether Jet Zeppelin Holdings was authorized to participate in the governor’s initiative.
Keefe leads DeSantis’ immigration fight
Keefe was hired by the governor’s office last September as the state’s first “public safety czar,” with a salary of $131,725. At the time, DeSantis said Keefe’s role would be “to protect Florida taxpayers from bearing the brunt of reckless immigration policies.” Since then, the state has imposed a series of rules and policies to target illegal immigration. Florida sent state police officers to the southern border in Texas at a cost of at least $1.6 million. cracking down on Florida shelters that provide housing and services to immigrant children on behalf of the federal government; sued the Biden administration over its immigration policies. and issued a broad executive order that, in part, “encouraged” state troopers to pull over drivers transporting immigrants into the state. In December, DeSantis also asked the GOP-controlled Legislature for millions of dollars to export Florida immigrants to other states, citing the wealthy enclave of Martha’s Vineyard. Vertol Systems Company doesn’t seem like an obvious fit to regularly fly dozens of people around the country. The company’s operations have focused on aircraft maintenance and support, pilot training and leasing of its helicopters to fisheries and other companies around the world. From 2000 to 2020, the company received more than $25.7 million in defense contracts for flight training, records show. Since news of the company’s involvement in DeSantis’ migrant flight programs broke, its website has gone offline. In April, its website said it operated four types of helicopters and three types of small planes with a maximum capacity of 12 people. (FAA records show the company owns 55 aircraft.) None of the company’s planes flew the 48 migrants to Martha’s Vineyard. Instead, flight records show Ohio-based Ultimate JetCharters flew them, apparently as a subcontractor. State contracting websites show no payments to the company. Ultimate JetCharters, which specializes in corporate shuttles, sports team travel and casino travel, has not responded to repeated requests for comment on how it became involved in the program or whether it would continue the project. Another round of Ultimate JetCharters flights had been scheduled this week to fly immigrants from Texas to Delaware — Biden’s home state — but were canceled without explanation, leaving the immigrants stranded in San Antonio. Since 2010, Vertol Systems and Montgomerie have used the law firm Keefe, Anchors & Gordon to represent the company in more than 20 lawsuits filed in Okaloosa County. The cases ranged from personal—like Keefe suing a drunk driver who crashed into Montgomerie’s Range Rover—to business, like suing a contractor Vertol Systems Company claimed stole its customer list and “trade secrets.” (The contractor was ordered to pay $2,500 and not compete with Vertol Systems Company.) In 2012, Keefe and Vertol Systems Company sued a Niceville lawn care company, Dogwood Services. A company employee mowing the grass at the Destin airport hangar stepped over a wire attached to one of Vertol’s helicopters. Vertol said it is entitled to compensation, measured against the cost of renting a similar helicopter. The defense argued that the helicopter had not flown for a month before the incident and had not flown for four months after the repair. The judge sided with Vertol Systems. Courtney Smith, then an attorney representing Dogwood, said she remembers it being a highly contentious case. And she remembers Keefe, who she said was particularly combative — a reputation he had in the area, she said. Smith, who now works in South Florida, said she can’t speak to how Vertol Systems operates, but that Keefe “will argue anything to be right.” She said she was not surprised to find out the company was involved in the migrant flights.
The company still represents the company
In 2017, Keefe was tapped by Trump to be the U.S. attorney for the Northern District of Florida, overseeing federal prosecutions for the state’s Panhandle and Gainesville. Keefe’s law firm dropped its name, but continued to represent Vertol Systems. In 2020, the company sued a Crestview employee who alleged he violated the company’s nondisclosure agreement. The employee claimed the violation stemmed from sending photos of workplace hazards to the federal Occupational Safety and Health Administration. The court sided with Vertol Systems and the employee was ordered to destroy or surrender any material. That same year, a New Zealand pilot who crashed one of the company’s helicopters while working in a tuna fishery in the Marshall Islands sued the company, claiming it still owed him more than $16,000. Three days later, the company sued the pilot, claiming the crash was due to negligent and/or reckless operation. The case is still open. And in 2019, Vertol took an aggressive approach after a pilot crashed and died during a fish-spotting mission near Micronesia. Jeffrey Lynn LaVere, a 39-year-old former US Army sergeant who served in the military for 17 years, worked for Vertol Systems as a contract pilot. About a year after his death, his wife filed a wrongful-death lawsuit in Oregon, where Vertol Systems is based. She said that four days before her husband crashed, he had texted her “expressing his concerns about the poor condition of the helicopter,” according to court documents. Seven days later, Vertol Systems filed its own lawsuit against the wife, claiming that as the representative of her husband’s estate, she owed the company money because the helicopter was damaged. In the complaint, lawyers for Vertol Systems said the crash was “solely the result of LaVere’s negligence and recklessness.” Lawyers for LaVere’s wife criticized the company’s lawyers for legal maneuvers that included removing her as administrator of her husband’s estate – and installing their own person as a replacement. “Our client is a young widow who has suffered…
