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The Freedom Convoy’s Renegade Jew

Benjamin Dichter, the free-thinking, radical nonconformist at the heart of Canada’s trucker protests, continues a long history of Jewish social activism

Armin Rosen
June 22, 2022
Original photos: Ed Jones/AFP via Getty Images; YouTube
Original photos: Ed Jones/AFP via Getty Images; YouTube
Original photos: Ed Jones/AFP via Getty Images; YouTube
Original photos: Ed Jones/AFP via Getty Images; YouTube

For two weeks this past February, Benjamin Dichter was thrust into the absurdist spotlight of modern political celebrity. A trucker-led convoy opposed to Canada’s digital COVID vaccine passport system had paralyzed downtown Ottawa, inspired the wildcat occupation and shutdown of several U.S.-Canadian border crossings, and provoked a quasi-authoritarian response from the Canadian government, which forcibly dispersed the protesters’ encampment, jailed the movement’s leaders, summarily froze their bank accounts, and seized, blocked, or escrowed nearly all of the estimated $20 million in non-bitcoin-based funds they’d raised. As chief media spokesman for the so-called Freedom Convoy, Dichter was the public face of one side of a shocking Canadian civic crackup. Depending on your point of view, the Freedom Convoy was either the unexpected culmination of the developed world’s COVID-era class war and a dark vision of the technocratic liberal state’s oppressive game plan, or an event that showed how easily marching hordes of ignorant and hateful populists could rise from the fringes to hijack a modern democracy. Dichter became the face of the former camp; the latter belonged to Justin Trudeau, dreamboat liberal champion and head of government of a country of 38 million people.

As the Ottawa police cleared the trucker protests in late February, convoy organizers like Tamara Lich were taken into custody and Dichter’s lawyers advised him to leave the Canadian capital—even a criminal mischief charge might subject Dichter to a gag order, they told him, making it illegal for him to speak about the aggressive law enforcement tactics he’d witnessed. “There were checkpoints every two blocks, police looking at people in cars,” he told me of his escape from downtown Ottawa by Uber. “And I’m like, ‘OK, I’ll put my hood up.’”

The Canadian government used a loose interpretation of terrorism financing rules to neutralize the convoy and its leadership even before Trudeau invoked the Emergencies Act on Valentine’s Day, becoming the first prime minister in his country’s history to resort to this civic nuclear option. For a period of eight days, Dichter said, “I was effectively de-banked completely. Credit lines, credit cards, my corporate account for my trucking company, myself, everything—everything was blocked.” Severing your opponents from their own money without due process, even for only a few days, is a highly efficient way of paralyzing them and discouraging any further activity you don’t like, which turns out to be as true in a boring and peaceful democracy as it is anywhere else.

Dichter briefly returned home to Toronto to regroup. By mid-March, he was in one of North America’s natural collection points for people who are nearing the end of some major ordeal, though in the majority of cases in Boca Raton that ordeal is nothing less than life itself. We met that month in a coffee shop under the shady archways of a floridly fake but also weirdly credible recreation of a Spanish plaza. The pieces of an oversize chess set stood arrayed for battle in a landscaped strip of lawn running through the middle of the complex. Twice in the course of our two-and-a-half-hour conversation, young children arrived to hurl the large plastic pieces at one another, which their parents would restore to their original position once the combat ended.

Even in uncool Boca, a supercar zooms by every few minutes. It took Dichter, sitting in the shade with his back to the street, just two attempts to correctly identify a black Corvette C8 roadster by the sound of its engine. “It has the baffles removed, that’s why it’s harder to tell,” Dichter explained of his initial failure, adding, “I always played music by ear, so I do everything auditory.” A nearby old man pushing a dog in a stroller, a startlingly poignant tableaux in Boca or anywhere else on earth, made no sound at all.

Dichter’s parents live in Delray Beach, Florida—his elderly father is now a daily minyan-goer, and Dichter had spent part of the morning taking him to shul. In a few days, Dichter, who is 46, would be leaving for a brief visit to Colombia, where he’d moved as a younger man after quitting his job as a project manager with Harley Davidson, picking up friendships and Spanish-language skills that are still intact. Later that afternoon, the Toronto-based gemologist-turned-commercial printer-turned-crypto investor-turned-podcast producer-turned-trucker-turned-Tucker Carlson- and Jordan Peterson-approved political lightning rod was heading to the house of “a very popular lesbian, Jewish, pro-Israel, journalist from Canada” for yet another interview.

Way back in February, Trudeau’s faceoff with the convoy looked like a major event in the history of North American democracy, an idea of government that both left and right believe to be in mortal danger from the other side. A lot has happened since then, including a societywide decision to move on from the pandemic, and a once-in-a-generation European war. But in the clearest sign that the convoy and the issues it raised would linger even as the event itself faded from view, Dichter openly wondered whether it was still possible for him to even live in Canada. “We may all have permanent flags on our banking record,” he explained of himself and other convoy-related figures who had their assets frozen. “So that means if I go to open another business account, or if we’re working on a foundation—anything—I’m going to get asked a whole lot of questions and maybe denied a bank account. Am I going to stay in that country if that’s my circumstance? No fucking way.”

Dichter wore a blank, ashy-green T-shirt and slightly baggy khaki shorts that stopped just below the knees. One of his lower legs was in a cast—he’d wiped out on an icy sidewalk in Ottawa during the frantic early days of the demonstration. Silvering hair topped a pleasant, reassuringly soft and strikingly youthful face. Nothing about his general bearing exposed him as any kind of a political flack. There were no points in the interview where it felt like Dichter was desperate for me to believe any of what he said, which is the difference between him and a professional flack, and also maybe part of the reason both Dichter and the convoy movement captured so much popular attention. At times he talked as if involvement in the convoy had just kind of naturally arisen out of the conditions of his varied and often itinerant life. “I look forward to being not-important again and getting back in my truck,” he told me. But at other times, he talked as if his participation emerged out of inescapable and specifically Canadian conditions, aspects of national life that troubled him and that also seemed to trouble a large number of his countrymen and countrywomen, people who had been formed within and against the mentalities and prejudices and neuroses of their homeland.

Dichter was adopted at birth—“there’s this very famous Canadian, Brigadier General Denis Whitaker, that’s our biological grandfather,” he said, referring to his three other blood siblings. His adoptive parents, the ones now in Delray, are Jewish, and he spent formative years in day school in Toronto. “Half of the day was Hebrew, and half of the day it was English until grade seven.”

After graduating from George Brown College in Toronto and HRD Antwerp, Dichter spent an unsatisfying five years in the gem trade—“I liked the science part of it,” he said of that abandoned first career—followed by a run of different jobs and his stint in Colombia. Years ago, Dichter explained, he had invented and patented a magnetic pad meant to protect the more delicate regions of male speed-bike riders, a shield against one of the literal hazards of the “crotch rocket.”

He bought bitcoin for the first time in 2015, giving him experience that later came in handy during the convoy, when around 100 truckers received $8,000 in bitcoin vouchers for fuel and other costs, which Dichter says is the only money out of nearly $20 million raised across various platforms that the Canadian government and its collaborators in the private sector failed to keep away from the demonstrators. He began producing podcasts for Tom Quiggin, a former Canadian intelligence officer whom Dichter described as “a real-life Jack Ryan.” Growing restless, Dichter exited the commercial printing industry after a decade of owning his own shop in Toronto. Then a biological brother of his who worked in law enforcement surprised him by asking: “‘Why don’t you get your trucker license?’ Where the hell is this coming from, I asked. He said, ‘Well, you sold your business, it’s just something to do, and they’re going to be increasing the price to get a license by, like, tenfold within the next six months.’” Dichter and his brother started making runs into New York and Connecticut in their very own Volvo VNL 670 semitruck just a few months before the pandemic hit.

The libertarian-minded Dichter developed an immediate allergy to Canada’s invasive public health regime. “The whole COVID thing, I really didn’t change anything,” he recalled, speaking of his own mentality toward the personal and communal health risk. This was a bit of a challenge in Canada, which has a civic religion of trust in benign government authority, and where national policy determines local conditions far more than in the United States. At the start of the pandemic, Trudeau demanded, and in many cases obtained, the personal authority to borrow and spend by decree—executive powers that would be unthinkable under the American system. But it was still possible to find dissenters, especially in small-town and medium-town western Canada, where Dichter says the COVID lockdowns were particularly disruptive. In Medicine Hat, in hardscrabble southeast Alberta, he had a podcast listener named Tamara Lich, a “politically connected” right-wing activist and one-time Albertan separatist of Metis indigenous heritage who had worked in the oil industry.

In 2018, Lich had organized a different trucker convoy to oppose various regulations on oil and gas in western Canada. “But they made the mistake of getting involved with the Conservative Party,” Dichter said, which he now disparages as “the spineless weasel” party. In 2014, at a time when he had far more confidence in the country’s partisan system, Dichter ran as a Conservative candidate for City Council in Toronto, earning what he calls a respectable 10% of the vote in a “communist” part of town. As Lich, Dichter, and other organizers contemplated a new convoy opposed to COVID lockdowns and Canada’s digitized national vaccine passport, Dichter advised against aligning the effort with any party or faction—even or especially ones inclined to support them. This is where other convoys, including the one that had recently circled the capital Beltway in Washington, D.C., went wrong, in Dichter’s view. By seeking the validation of officeholders, Dichter explained, their protest would be contained within the cheapening limits of partisan politics, when it should have been about something bigger and more important than the question of which segment of the elite should rule them. “If you notice, Ted Cruz did a photo op with the truckers and then all of a sudden there’s no more coverage anymore because it’s, ‘Yeah, I hear you, time for you guys to go home.’” He paused: “That’s not a knock against Ted Cruz particularly, especially since he’s a proponent of bitcoin. So thank God for that.”

It is the wariness of the convoy movement toward not just the ruling Liberal Party but the entire normal run of politics that made it appear so threatening to many Canadians. As J.J. McCullough explained in a March Washington Post column, “Many of Canada’s most determined ideologues are becoming quite skilled at physically disruptive acts of political rebellion,” leading to the “growing popularity of using force and physicality to alter Canada’s political conversation.” The truckers’ willingness to occupy the capital and shut down border crossings—a mirror to left-wing and indigenous activists’ successful shutdown of oil pipeline construction and drilling sites—presented an additional crisis for a fraying Canadian ethic of either voluntary or enforced social harmony. The Canadian equivalent of “life, liberty, and the pursuit of happiness” is “peace, order, and good government.” The convoy was a cry from beyond what many see as a stale and conformist political system whose helpful and conflict-adverse nature is enshrined in its very motto.

The convoy’s appearance of grassroots popularity made it even more alarming, especially to Trudeau and his circle. “There’s a guy by the name of Gerry Butts, we call him Trudeau’s brain,” says Dichter. “He’s the one who runs everything. Trudeau is just the mascot, or as he calls it, the ‘relationships manager.’ [Butts] was obsessed—obsessed—with the amount of money that we were raising because we out-fundraised every political party in Canadian history by a massive margin.” In the end, nearly all of that money was frozen, effectively blocked from being transferred to the truckers by private platforms like GoFundMe, or placed in escrow pending the results of a nuisance lawsuit against the convoy’s organizers. Even with their money withheld, the convoy was considered so dangerous to peace, order, and good government that Trudeau himself accused it of “hate, abuse, and racism,” the prime minister reaching somewhere close to the uppermost rung on the contemporary rhetorical escalation ladder.

Trudeau wasn’t the only one to characterize the convoy as a bigoted enterprise. Other critics honed in on a specific alleged bigotry: A column in the Toronto Star claimed that the convoy taught “timely lessons about the current face of antisemitism,” noting the presence of “a Nazi flag as well as other hate symbols” in downtown Ottawa, as well as the suspicious (and in the writer’s view, bad-faith) enthusiasm of convoy leaders for condemning the bigots in their ranks. The Anti-Defamation League drew on hacked information about donors who used GiveSendGo, the “Christian crowdfunding site” the convoy turned to when GoFundMe refused to transfer nearly $10 million in donations to protesters, to speciously connect the convoy to the January 6th siege of the U.S. Capitol. Dichter is not shy about sharing his belief in the fecklessness of the organized Jewish community, most of which doesn’t share his outlook on much of anything, and which he sees as doing little to help Jews or the world in general. He noted that a racist and antisemitic “troll” named Pat King who had been arrested at the Ottawa demonstration was still in custody. “I keep trying to communicate to people in the Jewish community that are celebrating this,” Dichter said. “The guy is being held because he says stupid things on the internet, and that’s a problem. He’s still in jail.” (King has been charged with various offenses related to obstructing a police operation and disobeying court orders, though some free speech advocates see these cases as pretextual.)

“If there’s something I could change within the Jewish community,” he said, “they’ve got to learn to be more libertarian. They got to learn to tolerate opinions they dislike and engage with people they dislike … right now, you’re fundraising around calling people names. And then you wonder why people don’t like us.”

Dichter made it clear he would rather not have discussed his Jewish identity at all in connection with the convoy, believing it irrelevant to the many serious issues at hand. But there is a rigid logic to how one rebuts an accusation of bigotry in the present day. “I didn’t like the fact that I had to tell people I was Jewish, but the political left is so obsessed with identity politics, and branding—everything is neo-Nazi and whatever—that I had no choice but to say, ‘Listen, Justin Trudeau, I’m Jewish, and unlike your brother, who’s made a career of producing Israel apartheid videos, by the way, I have family buried in mass graves in Europe.’ That’s the clown world we live in, and because they’re so obsessed with this as a tactic, I had to mention it.” (Dichter was exaggerating for effect here: Alexandre Trudeau is a conflict reporter and filmmaker who has written positively about Fidel Castro, and who made a 2004 documentary that cast the head of the Al Aqsa Martyrs’ Brigade in an apparently positive light.)

In Canada, the periphery can feel crushed and stifled by the center. Unlike in the United States, it has little systemic recourse to recover any sense of control.

Dichter is no revolutionary. His diagnosis of what ails Canadian life amounts to an unsystematic, mild populism that sees the basic unfairness and unfreedom of society as being imposed from above by a cross-partisan sliver of the national elite. “They’re extremists. And extremists can’t see beyond their own worldview. They only see their view,” Dichter said of Trudeau and Butts. I suggested that perhaps Trudeau was the opposite of a radical, and that using aggressive and novel extraconstitutional powers to crush your opponents has become a perfectly mainstream instinct in a time when vast numbers of people see the political opposition as Nazis or communists or some other variety of unthinkable and active threat to civilization. Polling bears out the idea that, whatever else he is, Trudeau could pass for a boring centrist. As McCullough noted in his Washington Post column, two-thirds of Canadian voters wanted the military to break up the trucker occupation of Ottawa. According to Dichter, though, the country’s problems lie not with a compliant citizenry but with a venal and autocratic ruling class. Ordinary Canadians, he believes, understand what’s going on. “There’s an ungodly amount of momentum and support for us,” he claimed.

In Dichter’s telling, the convoy became a proxy for Canada’s stark regional divisions, which resemble some of America’s own geographic splits. The U.S. federalist system began as an attempt to balance the interests of small and large polities; true to this intention, both the Electoral College and Congress, and even the apportionment of state-level elected delegates in places like New York, can give peripheral areas an effective veto over key aspects of policy inside of densely populated cities, which now exist in an entirely different world than small towns even a few hours into the hills. As Dichter sees it, Canada has its own mutually embittering divide between the center and the periphery, worsened by the fact that Canadian politics do not operate under a federalist system of intricate regional negotiation. In Canada, the periphery can feel crushed and stifled by the center. Unlike in the United States, it has little systemic recourse to recover any sense of control.

“When I was in Alberta, about six months before COVID, certain towns and certain smaller cities—Grande Prairie, Medicine Hat—were being turned into third world cities,” Dichter recalled. “And I can tell you that because I’ve traveled extensively throughout the third world and growing up, I always had family in Alberta.” This observation recalled then-candidate Donald Trump’s seemingly obnoxious statement that downtown Harrisburg, Pennsylvania, “looked like a war zone”—although enough Pennsylvanians apparently agreed, since it was slight Republican gains in the state’s Rust Belt that helped deliver the real estate huckster the presidency.

Canadians discontented with the country’s social and regional tensions had no perceived ally within the mainstream political system the way the dispossessed of central Pennsylvania thought they did. Then COVID arrived, bringing with it some of the strictest lockdowns in the democratic world, policies Canadians in declining rural or energy-producing regions couldn’t escape, just as they couldn’t escape environmentally minded edicts from Ottawa meant to constrain oil and gas production. There was a time, Dichter said, when western Canada “was supporting the rest of the country through its energy sector. And now the Trudeau government decided just to turn off the switch and people had their lives ruined, their businesses ruined.”

Dichter is a globe-trotting, vaccinated, Jewish, tech-savvy Torontonian, hardly anyone’s idea of a frontier populist. But he knew enough about his country’s social divisions to know what side he was on, regardless of where he lived and what his life looked like. Dichter explained that one of his heroes is British journalist James Burke. “I grew up watching all his shows and documentaries and stuff, and he talks about how people in the modern era look to technology to solve their problems.” For example, Dichter said, consider the metropolitan faith that lockdowns and laptops could beat COVID. “Whereas people who live in rural communities and rural areas, they’re a lot more independent. So it’s a completely different worldview, and I don’t know if it’s both sides, but it’s definitely one side, that just doesn’t care to hear about the grievances of people in rural communities.” The sense of alienation in outlying Alberta explains the true origins of the convoy, even if the protest drew in supporters from every part of Canada. “That’s why it started from out west.”

I had been warned before meeting Dichter that it was unclear if he ever had any real standing within the convoy movement. Dichter had been one of six members of the Freedom Convoy board, yet he also showed a near-total lack of ego about his own role in a potentially defining event in his country’s recent history, a stance that struck me as entirely genuine. The most powerful person in Canada knows who you are and hates you, I pointed out, hoping for a colorful boast or additional anti-Trudeau trash-talk in reply. That’s a weird and potentially very uncomfortable position to be in, right? “I don’t really care,” he responded, as if he’d never thought of it that way before. “Honestly, it doesn’t bother me in the slightest bit.”

In a couple of weeks, he explained, he’d be speaking at Miami’s annual bitcoin conference, during which he’d announce the movement’s next steps (which he declined to explain). It seemed unlikely to me that the convoy rank-and-file would be paying much attention to any bitcoin conference, or to him (especially now that bitcoin has lost over half its value since April). But he happily admitted that the next phase is out of his hands. The fate of possibly $5 million in donations to the truckers that the Canadian government froze that is still in escrow depends on the outcome of a lawsuit against the trucker convoy filed in the name of a photogenic 21-year-old activist, a so-far effective means of using the legal process to deprive opponents of the government of money that is rightfully theirs. Lawyers are keeping him updated on the case, Dichter says, though he didn’t seem like he was all that closely involved. Remnants of the trucker movement were still on the move, he explained, waging protests and miniconvoys across Canada. “I saw there was a convoy that they did in Ottawa. They went to the Amazon facility. That apparently got a lot of attention,” he said. It was all out of his hands, as it might always have been.

Dichter, at least, is the image of a not very ideologically driven populist, someone whose views emerged from gradual life experience rather than some punctuated break with mainstream society. That’s how most people think and live in the world, although populist uprisings are also seldom defined by their most prudent and even-minded participants. “I ride a motorcycle 320 kilometers [200 miles] an hour,” Dichter said of his initial, not-unreasonable reaction to the COVID lockdowns. “I don’t need the government to tell me what I can and cannot do.” At my prompting, he clarified that this Canadian-denominated speed milestone was achieved on a closed racetrack, rather than a public highway.

Armin Rosen is a staff writer for Tablet Magazine.