As former President Trump travels around the country airing grievances and fighting to reclaim power in between arraignments and court appearances, he is flying with a pilot who is quite friendly to his conspiratorial and authoritarian brand of politics. The man who says he is piloting the former president’s “Trump Force Two” private jet is a hardcore MAGA activist who urged people to go to the Capitol on Jan. 6, according to a TPM review of his social media posts.
Pilot Vincent “Vinny” Caldara first zipped his way into Trumpian airspace during the 2016 race when he piloted the jet that soon-to-be Vice President Mike Pence used on the campaign trail. Caldara was forced to resign after The Guardian reported that he was facing criminal charges (later dropped) for allegedly trying to run someone over with his car. It was a minor scandal of the early Trump era, but now, Caldara is apparently back in the cockpit.
The story of the fall and rise of Trump’s pilot is another example of how, in his bid for a second term, the former president is re-embracing figures who he previously had to distance himself from due to political and legal controversies. Like more high-profile advisers Roger Stone and Steve Bannon, Caldara serves as an example of someone who returned from prior exile as Trump has increasingly ignored moderating influences on his team and catered to the more extreme elements of his base. On the campaign trail, Trump has surrounded himself with true believers, and that trend apparently extends to his flight crew.
Caldara is one of several right-wing figures who participated in OperationFlagDrop, an encrypted Telegram chat led by self-described Proud Boy Dion Cini and far-right House candidate Tina Forte in the aftermath of the 2020 election. In his posts on the channel, Caldara claimed to have conferred with My Pillow pitchman Mike Lindell, one of the most prominent promoters of conspiracy theories that deny Trump’s loss in 2020 about plans to impose martial law. Caldara also expressed utter devotion to Trump, who he once called a “godsend” and “a messenger.”
New reporting from TPM reveals both Caldara’s participation on the activist fringe and the fact he appears to be flying for Trump.
In recent months, Caldara has posted several photos on Facebook from the cockpit of one of Trump’s planes, where a miniature bobblehead of the former President sits on the dashboard, as well as a photo of a challenge coin issued to Secret Service agents responsible for travel. Caldara has bragged that he will “command Trump Force Two in ‘24,” referring to a Cessna Citation business jet Trump uses.
Caldara, and an attorney for Caldara didn’t respond to requests for comment.
The Trump campaign did not initially return TPM’s request for comment. One day after publication, a campaign spokesperson told TPM: “He is not a pilot for us and has not been on any campaign trips. There is no ‘Trump Force Two.’ If you’re referring to the Citation, it has not been used for many years.”
Caldara’s position illustrates how members of the far-right remain critical to the nexus of power around Trump. In this case, an active participant in a Telegram chat group with two Proud Boys members convicted of seditious conspiracy, who expressed the belief after Jan. 6 that Trump would act on MyPillow CEO Mike Lindell’s advice and declare martial law, is now flying his plane. In addition to flying Trump, Caldara has also doubled as a street-level activist for the MAGA right, organizing rallies in south Florida while burnishing his credentials as a former police officer.
While there is no indication Caldara was among the crowds who broke into the U.S. Capitol on Jan. 6, he clearly took part in the protests against Trump’s loss in Washington D.C. that day. Videos Caldara recorded on Jan. 6 and posted to Facebook show him standing in a window at The Willard Hotel, where Trump’s team had its Jan. 6 “war room,” and exhorting crowds below. Previously leaked documents also indicate that Caldara was on the list of VIP guests for Trump’s speech on the Ellipse where the former president railed against his defeat and urged crowds to march to the Capitol.
“Tens of thousands of people are storming the U.S. Capitol,” Caldara said in his Facebook video. “They’ve already gone down to the Capitol. They’ve knocked down all the fencing, they’ve climbed the steps, and the only thing keeping them from going into the Capitol are the Capitol Police.
“Fortunately for the Capitol Police, we are not BLM, we are not Antifa. We defend the police, we don’t defund them,” Caldara said. He added later: “We are going to stop the steal, and we’re not leaving D.C. until this gets taken care of.”
Well before Jan. 6 and Trump’s election, Caldara was an active supporter of the then-candidate. During the 2016 race, he helped marshal police support for Trump by chairing his “Florida law enforcement coalition” and ferried Mike Pence around as his pilot. However, Caldara lost his position on the Pence plane after The Guardian published an expose revealing that the pilot faced a charge of aggravated battery with a deadly weapon for purportedly running a man over with his car, and faced a civil suit from a woman who claimed that Caldara tried to run her over with his Harley Davidson.
Court records show that Caldara fought the criminal case until October 2017, when prosecutors told the court that they would no longer pursue the matter. A judge dismissed the Harley-Davidson civil suit in January 2018, finding that Caldara had never been served with the complaint.
Throughout Trump’s four years in office, Caldara appears to have stayed involved at the edges of Trumpworld. He appeared at Mar-a-Lago in February 2017 during the visit of Japanese Prime Minister Shinzo Abe. Caldara has written that he worked as a White House Advance Team volunteer under Trump, receiving free travel and accommodations in exchange for helping prepare for presidential visits.
The pilot’s role with Trumpworld seemingly evolved over time. In 2016, he was promising Trump “security” for his rallies via the Florida law enforcement association, Later on, Caldara was on the streets with Trump supporters.
By summer 2018, Caldara had joined up with Dion Cini, a pro-Trump activist and self-described member of the Proud Boys known for “flag drops” in which he would unfurl massive Trump flags in unexpected places. This led to Cini being banned from Major League Baseball and multiple theme parks. But to Caldara, that was apparently an attractive resume.
Caldara, per a description posted on the OperationFlagDrop Facebook page, helped Cini create the first group for the project on that site. Photos and video show the two of them grinning as they displayed massive Trump and MAGA flags. Caldara was also a regular participant in Cini’s inflammatory OperationFlagDrop Telegram channel.
In the months after the 2020 election, Caldara’s activism placed him at the center of groups which would go on to organize the rally at the Ellipse on Jan. 6. He had also begun recording Facebook videos, garnering him attention and a small following among Trump diehards.
Caldara appeared at a Dec. 11 rally in Washington D.C. where four people were stabbed during street clashes. In one video, Caldara gushed over an appearance from Roger Stone. In another, he posed for a selfie with Tina Forte.
In the weeks that followed, Caldara traversed the country with the March for Trump bus tour and
Women for America First two groups that played a major role in organizing the Jan. 6 Ellipse rally. Per an interview with the Palm Beach Post, Caldara visited more than 15 states during that period with the “Trump Train.”
It all built up to Jan. 6.
As the day descended into violence, Caldara initially expressed excitement in videos he took from The Willard hotel. It’s not clear whether Caldara made it into the “war room,” the inner sanctum of Stop the Steal efforts that purportedly included Rudy Giuliani, attorney John Eastman, and Steve Bannon, among others. However, it is apparent that Caldara was hoping the day’s action would help Trump stay in power.
In one video taken as crowds marched down Pennsylvania Avenue towards the Capitol, Caldara said, “[Trump] has got a lot more tricks in his bag. And we’re here to make sure he exercises every single one of them.”
Even after the Capitol insurrection failed to keep Trump in the White House, Caldara refused to believe that President Biden would take office. Texts from the Operation Flag Drop chat show Caldara replying to one disillusioned member of the channel who complained that Trump failed to disavow the widely discredited Kraken and Q proponents like Sidney Powell and Lin Wood, leaving a “false hope narrative that have Trump supporters disillusioned for decades to come.” Caldara responded by touting his own connections and implying their chance of successfully reversing Trump’s loss was very real.
“Have you seen the evidence? Have you met with these people you claim are lying? Have you had closed door meetings with Mike Lindell, the MyPillow Guy, who is financing these attorneys and assisting with the investigations by providing logistical support and the exclusive use of his private jet?” Caldara shot back. “I’ve met with them while I was in Atlanta and DC.”
After the person replied by calling Caldara and Lindell “delusional,” the pilot retorted: “Now Mike Lindell is ‘delusional’ and talking ‘gibberish’? Yeah, ok. Good luck with with that.”
Caldara kept the faith as the months after Biden’s inauguration wore on. In one July 8, 2021 video taken from a highway overpass near Mar-a-Lago where he was hanging Trump flags, Caldara called Trump a “godsend” and “messenger.” Michael Flynn and Lindell, he added, would finally succeed in overturning the 2020 election that year.
Caldara tried to keep up the momentum in the years after President Joe Biden’s inauguration. Caldara bought an ambulance with a fellow Trump supporter in June 2021. The pair dubbed it “Rescue 45” as part of an elaborate extended metaphor for what they saw as the need to resuscitate America after Trump’s departure from office. And as always, it’s hard to draw the line between genuine, albeit desperate belief and grift. In the case of Rescue 45, documents show, the ambulance doubled as the lynchpin of a business plan to sell “Rescue 45”-branded merchandise.
Videos and social media posts show Caldara beaming in front of the ambulance, but the venture ended poorly. In April 2023, an associate sued Caldara in Palm Beach County court for $50,000 in damages, accusing him of damaging and then “absconding” with the ambulance before trying to re-title it in his name only.
That suit remains unresolved. Caldara has not yet submitted a reply, per the docket.
Even though he never seemed to fully believe the last election ended, social media postings from Caldara show he is all aboard with Trump’s reelection, too — literally.
In February 2023, Caldara posted a series of photos from Trump’s 757, also known as Trump Force One. The next month, Caldara posted an image of what appeared to be a Secret Service coin while tagging Mar-a-Lago as the location. The reverse side featured a Special Services Division insignia, described by the agency as “responsible for safeguarding transportation at every aspect of the protective mission.”
One video Caldara posted on July 25 appears to show him in the jumpseat of the cockpit of Trump’s plane.
“Looking forward to once again commanding Trump Force Two in ‘24,” he wrote, referring to the Cessna Citation business jet which Trump uses.
Along with photos of him in front of Trump’s 757, Caldara posted lyrics from a Warren Zevon song about returning to the “high life.”
“I am back in the high life again
All the doors I closed one time
Have opened up again
I am back in the high life again
All the eyes that watched me once
Will smile and take me in.”