A Trump voter proved the MyPillow Guy wrong. Now he wants his $5 million.

Eight months into Joe Biden's presidency, the MyPillow guy, Mike Lindell, staged an event in Sioux Falls, South Dakota, that he promised would return Donald Trump to the White House. The three-day Cyber Symposium revolved around a mysterious cache of computer data that Lindell had surreptitiously acquired. In his telling, the data proved that Chinese hackers had manipulated American voting machines into securing Biden's victory.

"The election was stolen, and we're proving it right here, aren't we?" Lindell crowed to some 200 attendees on the first night, sweating through his suit. "President Trump is the rightful president, are you with me?"

One attendee, Bob Zeidman, who had voted for Trump twice, hoped this was true. A mild-mannered, 64-year-old Republican, Zeidman chafed at the former president's demagoguery. But he's more repelled by the Democrats, whom he believes have "gone so crazy with their wokeness and socialism." As an authority in software forensics — the art of digital problem-solving — Zeidman has been an expert witness in more than 260 court cases, including the 2021 Supreme Court battle between Oracle and Google and the fight between Mark Zuckerberg and the Winklevoss twins. He wanted to see the evidence of vote rigging that Lindell claimed to have collected, and he was open to the possibility that a vast conspiracy, including Democrats using mail-in voting and ballot harvesting to fabricate votes, had stolen the election from Trump.

"There was fraud in the election because there's fraud in every human endeavor," Zeidman said. "How much fraud? I don't know." He had traveled to Sioux Falls intending to find out.

Lindell had purchased his prized data for some $1.5 million from a software developer named Dennis Montgomery. In the early 2000s, Montgomery had won millions of dollars in Pentagon contracts after he convinced the CIA that he had built software that could intercept terrorist messages concealed in Al Jazeera broadcasts. But it turned out to be a hoax: A top CIA official called Montgomery's software "imaginary voodoo" and "bullshit," and one of Montgomery's own lawyers called him a "con artist" and "a habitual liar engaged in fraud." But none of that bothered Lindell. He praised Montgomery as "one of the smartest people that has ever walked this Earth." And to prove his confidence in Montgomery's data, he announced a high-stakes wager: If anyone at the Cyber Symposium could demonstrate that the data did not show election meddling, he would award them $5 million. He called it the Prove Mike Wrong challenge.

Bob Zeidman has many obsessions, and one of them is poker. He lives in Las Vegas, where he competes in poker tournaments every week. He entered the Prove Mike Wrong challenge with low confidence he would win the exorbitant pot, estimating he had a 0.5% chance of disproving Lindell's "evidence." Still, as he later wrote in a lengthy LinkedIn post, he would have a "100% chance of being able to write about what would certainly be one of the most interesting and important conferences in recent history."

But as Zeidman analyzed the reams of data provided to him and the other cyber experts at the symposium, his confidence rose. When he converted the data into a Word document, he discovered it was filled with line after line of meaningless letters and numbers. It was as if somebody had typed in what they imagined computer code might look like. "I confirmed that it was perfectly formatted, legitimate gibberish," Zeidman said. "In other words, it was a real Word document filled with gibberish, not a document that Word didn't understand." Even more suspiciously, the data files were time-stamped to just a few days before the symposium, meaning they were likely created for the event, not collected from errant voting machines. The numbers purporting to demonstrate election fraud, Zeidman concluded, were themselves a fraud.

By the second day, Zeidman was certain he had disproved Lindell's claims. He filed a damning report and registered a copy online with the US Copyright Office as proof he had written it by the contest deadline. Then he called his wife from the hotel parking lot. "All I want to say," he told her, "is that you should start thinking about how you want to spend $5 million."

After returning home to Vegas, Zeidman waited to hear from Lindell's people about the award. Though he is already a multimillionaire, with several patents and businesses to his name, $5 million remained an exciting prospect. Antsy with nervous energy, he upped his poker playing. But as a Trump backer, he was puzzled by the obvious fraudulence of the data, which he laid out in his LinkedIn post: "Was someone sabotaging Mike's data? Or had Mike been bamboozled? Or was Mike the bamboozler?"

Several weeks later, Lindell's team finally got back to Zeidman: They were refusing to pay up. Zeidman, they argued, had failed to meet the requirements of the challenge, which stipulated that a winner must prove "to 100% certainty" that the data was not "related to the election."

Undeterred, Zeidman sued one of Trump's most vociferous advocates for contract violation. In February, after days of deliberation, an arbitration proceeding in Minnesota sided with Zeidman. He had indeed Proven Mike Wrong, and now Mike must pay.

Soon after the ruling, I arrived in Vegas to meet Zeidman. His handsome home sits in a gated community in Sumerlin, a residential area in the high desert. A "Stand With Israel" sign adorned his front yard. He and his artist wife, Carrie, collect modern art, which crowded the walls of their living room. Out back was a large pool. Recently, after Zeidman started swimming regularly, he became frustrated with trying to keep track of his laps, so he invented a counting instrument to do it for him. A newly patented prototype sat on the kitchen counter.

I was interested in what impact, if any, Zeidman's experience with Lindell had made on his politics. Lindell, for all his cartoonish bombast, has clearly been following a path of election denial forged by Trump. It is Trump, after all, who has made his case for voter fraud the centerpiece of his reelection campaign. The fabrications have been wildly successful at firing up his base: Recent polling suggests that nearly 70% of Trump's supporters believe that the 2020 election was "stolen" by the Democrats.

Zeidman, though sympathetic, is not fully on board. "What Lindell is doing is hurting America and hurting Republicans, because it's dividing us and it's wrong," he told me. "I've had a few other Republicans say to me, 'OK, but you don't have to broadcast this.' And I say, 'No, it's the truth. The truth has to be out there. We allegedly stand for the truth, OK? Not the relative truth, but the absolute truth.'"

Zeidman requires constant stimulation. During meetings, he makes sure to sit by a door in case boredom forces him to flee. Whenever he's idle, he becomes "terribly depressed." To keep busy, he invents gizmos and software. He pens satirical political novels and computer-science textbooks and conservative op-eds on his Substack or for publications like the Cleveland Jewish News. He adores movies, though plot holes ruffle him. His favorite film is "Memento," because "it all connects together." He speaks regularly at engineering conferences and attends political ones.

Since young adulthood, Zeidman has "leaned conservative." But it was not until the presidency of George W. Bush that he started going to political events and closely following party politics. He describes himself as a "rare species": a Republican Jew. American support for Israel is one of his chief concerns. He remains a great fan of Bush.

He has always found Trump distasteful: "He's a really nasty guy." Yet he understands Trump's appeal as a totem of conservative grievance, much of which he shares: left-wing media bias, high taxes, political correctness. He pinpoints the genesis of Trump's rise to Mitt Romney's loss to Barack Obama in 2012.

"The Democratic Party attacked Romney so strongly on moral issues when this man was an outstanding moral leader," he said. "I think that pissed off so many people that they said, 'OK, whoever we put in office is going to be trashed, so let's find a guy who trashes back.' And that was Trump."

Another guy who trashes back is Mike Lindell. After numerous failed ventures — a bar, a food truck, a carpet-cleaning business — the Minnesota native found wild success with his company MyPillow, which he claims hit revenues of $300 million in 2018. His zany infomercials, signature mustache, and Midwestern whimsy became a TV staple across the country. (Zeidman himself is a happy customer; he enjoys the pillow's "slumber-inducing qualities.") Even more impressive, Lindell prevailed after overcoming a severe crack addiction, as recounted in his memoir "What Are the Odds? From Crack Addict to CEO." In recovery, he became a committed evangelical Christian. Trump, he believes, was "chosen by God" to be president.

In his transactional way, Trump has returned the compliment. Following his victory in 2016, he invited Lindell to meet him in Trump Tower. Since then, the two have appeared together at the White House and at campaign events. In March, during a rally in Wisconsin, Trump praised him as "the great, legendary Mike Lindell." Lara Trump, Trump's daughter-in-law and the new cochair of the Republican National Committee, hawks MyPillow products on her podcast, "The Right View."

But no amount of praise can make up for the losses Lindell, now 62, has endured for his favorite president. In a defamation suit brought by the voting-machine firm Dominion Voting Systems, Lindell and MyPillow were found liable for a staggering $1.3 billion in damages, which far exceeds his net worth. Lindell's lawyers have since quit, because, they say, he has not paid them. Another defamation case brought by the voting-machine firm Smartmatic is ongoing. Recently, Lindell claimed he had just $10,000 left to his name.

When I spoke to Lindell, he balked when I asked if he regrets his decision to wage a one-man crusade against electronic voting machines. "Do I regret spending $40 million trying to save our country to get rid of these computers?" he boomed. "No!" He repeatedly disparaged Zeidman as "not a cyber expert," which is patently untrue. "It was all contrived," he said of Zeidman's report. "Whatever their plan is, whoever he's working with — it's disgusting what he's trying to do."

Under deposition in the arbitration proceedings over his refusal to pay Zeidman, Lindell was a tornado of evasion and contradiction. He claimed, confusingly, that the 23 gigabytes of data he bragged about at the Cyber Symposium were not actually intended to prove election interference; they were only "related," in some unspecified fashion, to the 2020 election. Moreover, he said, he could not make public the parts of the data trove that do prove election interference for reasons of "national security." With a Trumpian redirect, Lindell assured Zeidman's lawyer, Brian Glasser, that he had far more shocking evidence in hand — but he was being blocked from releasing it by a "government gag order" issued by a judge in Nevada.

"It's the same data we're talking about as it relates to the Cyber Symposium?" Glasser pressed.

"No," Lindell said. "I think it goes a lot deeper than that." The explosive evidence, he implied, would prove that Zeidman was wrong: The election was stolen. "Dennis Montgomery has a lot more than just that data," Lindell insisted.

Later, Zeidman's lawyers tracked down the case Lindell was referring to. Nobody, it turned out, was preventing Lindell from releasing any data. The so-called "gag order" was issued in 2007 as part of a contract dispute between Montgomery and eTreppid Technologies (the company Montgomery ran that had defrauded the government), relating to government contracts and related "trade secrets." Lindell had filed a motion to remove the order, arguing that he somehow needed to release the data to defend himself in his unrelated defamation cases. The court denied his request, saying the order didn't apply to him. "Lindell provides nothing more than speculation," the court wrote, "that he will somehow be precluded from presenting this information because of the protective order in this litigation." In December 2022, Lindell said he would release the data within 60 days. He never did so.

Zeidman pities Lindell for what he sees as his sincere conspiratorial convictions. "Some people believe the world's out to get them because they think they are doing everything rationally but the world is not acting rationally in response, when really it's the other way around," he said. "I think that's the way Lindell is. He's angry because he doesn't understand why people don't believe him. In his mind, people irrationally hate him for telling the truth."

In Vegas, Zeidman drove me to The Venetian for lunch, where he had a poker tournament later that afternoon. On the way, he gestured toward the Trump International Hotel, towering over Sin City like a giant golden Zippo. Long before Trump ran for office, Zeidman had followed his business ventures with bewilderment.

"He would run his businesses into the ground yet somehow make a windfall profit and get investors to invest in his next project," he said. "I'm thinking, don't they look at the records and see that people have gotten burned by him? Why would they invest in his next project? How can he talk them into that?"

Yet for all his problems with Trump, Zeidman sees the incumbent as no less deceitful. "Biden is the Democrats' version of Trump," he said. "He's a liar. He's uncouth. He says stupid things and insults people." This equivalency struck me as an exaggeration of Lindellian proportions. But Zeidman stood by it.

In all likelihood, he said, he'll be voting for Trump come November. "I don't want to vote for Trump because he's scary, but I can't vote for Biden," he said. "For me, the decision is: Biden's policies have made America weaker and Trump's policies made it stronger."

On the way to The Venetian, Zeidman stopped by his bank to retrieve cash for the tournament buy-in ("This one is $800, which is relatively cheap"). He was already strategizing. "The way to win a poker tournament is to survive until later in the tournament," he explained. "It doesn't really matter how many chips you have, because later in the tournament, the blinds — the minimum bets — are so big that one hand can flip everything."

At the casino, hundreds of players sat silently at small tables in a windowless poker room. The exchange of chips crackled through the stale air like the snapping shrimp of coral reefs. Zeidman competed until 2 a.m. The next day, he came in 10th out of 330 players, earning a $1,000 profit.

"I was happy," he told me. "But the big money is really at the top."

It is unlikely that Zeidman will see his $5 million from Lindell. Lindell is appealing the binding arbitration ruling in federal court. In March, his lawyers subpoenaed records of Lindell's financial assets, but Lindell's new lawyer has been slow to respond. Zeidman suspects that Lindell will try to transfer his assets out of his company, Lindell Management, which, legally speaking, is the offending party in their dispute. When we spoke, Lindell wanted to make that distinction clear. "This isn't against me," he said. "This was against Lindell Management, a management company that managed that event and other events. You know that, right?"

Still, Zeidman is glad to have Proven Mike Wrong. He had played his part in disseminating an important truth. "I think most Republicans don't believe Lindell now, and maybe I had a part in that," he told me. Then he added: "But they still believe the election was stolen through ballot harvesting" — allowing political campaigns to collect and submit absentee ballots on behalf of voters — "and things like that."

I asked the obvious follow-up: Does Zeidman believe this improbable claim, which numerous studies, scholars, legislatures, and judges have thoroughly disproven?

He isn't sure. "I have no idea if things would have been different if we didn't have all the ballot harvesting and mail-in ballots," he said. "I just don't know."

An inveterate engineer, Zeidman avoids too much speculation. He prefers the hard certainty of numbers: differentiating complex code, investigating algorithms, analyzing technical patents. These are the skills he used to debunk Lindell's data. What Zeidman is sure about, and what worries him most, isn't election interference. It is the perilous state of the country that those elections, as he sees it, have produced: woke lunacy, border instability, unrestrained crime, and rising antisemitism. Trump, he concedes, is no paragon of order. But if the former president can mend all of that, then perhaps he is the only logical choice. A guy like Bob Zeidman looks at America and wonders: Where did all the rational people go?

Brent Crane is a reporter based in San Diego. His work can be found at www.brent-crane.com and @bcamcrane on X.  

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