Trump’s Quixotic Quest to Win the 2020 Election

Oct 23, 2025 05:40 PM EDT, Thu

As the White House hires another ‘Stop the Steal’ lawyer, failure is inevitable

Trump has hired a lawyer to oversee yet another investigation into his 2020 defeat, apparently because the original probes were too reality-based for him.

Oct. 20, 2025, 3:30 PM EDT By Steve Benen

Ed Martin, one of the nation’s more notorious “Stop the Steal” lawyers, has already been rewarded with powerful and influential positions on Donald Trump’s team. He will not, however, be the only such attorney working within the president’s operation. The Wall Street Journal reported:

A former Trump campaign lawyer who worked on the effort to overturn the 2020 election results has joined the administration to investigate that year’s election and voting-related issues, according to people familiar with the matter. Kurt Olsen, a lawyer who unsuccessfully pushed claims of voter fraud, has joined the administration as a ‘special government employee,’ some of the people said.

According to the Journal’s report, which has not been independently verified by MSNBC, Olsen will be working directly with the president. The lawyer has also reportedly taken an interest in voting machines, while “asking intelligence agencies for information about the 2020 election.”

About a year ago, with time running out in the 2024 presidential election and early voting underway across much of the country, then-Sen. JD Vance refused to answer questions about who was the rightful winner of the 2020 race. The Ohio Republican complained at the time that political journalists were “obsessed” with the election from four years earlier.

A year later — and roughly five years since Trump lost his re-election bid — someone is “obsessed” with the 2020 race, but it’s not political journalists.

Indeed, on a nearly daily basis, the incumbent president continues to whine about his defeat five years ago, pretending that he secretly won despite the results and peddling discredited conspiracy theories intended to rewrite history. (Last week, for example, the Republican brought up the 2020 race, unprompted, Sunday, Tuesday, Thursday and Friday. This was not an especially unusual week.)

Now, evidently, Trump has even brought on a lawyer to tell him what he wants to hear.

The trouble is, we’ve already been down this path. In 2023, The Washington Post reported on Trump’s political operation having hired the Berkeley Research Group to scrutinize the 2020 election. The purpose of the contract was obvious: The then-outgoing president and his team wanted the researchers to bolster Trump’s conspiracy theories about voter fraud and election irregularities.

That didn’t work out well: BRG couldn’t find any meaningful evidence. As my MSNBC colleague Hayes Brown joked, Trump “must have really hated that his campaign spent over $600,000 to be told he was wrong.”

We later learned that BRG wasn’t alone in tackling this endeavor. Months later, the Post published a related report on Team Trump paying $750,000 to Simpatico Software Systems, which was also tasked with finding evidence of 2020 voter fraud. That didn’t go well, either: The company was unable to tell Republicans what they wanted to hear because the evidence simply didn’t exist.

Ken Block, the owner of Simpatico Software Systems, later an op-ed in USA Today, published with a striking headline: “Trump paid me to find voter fraud. Then he lied after I found 2020 election wasn’t stolen.”

In his opinion piece, Block, a former Republican gubernatorial candidate, explained that his investigation failed to turn up meaningful evidence of voter fraud, adding that rank-and-file GOP voters have been fed “a steady diet of innuendo, misrepresentations and outright lies” on the issue.

I mention this because Trump has already initiated investigations into his 2020 defeat. These investigators were motivated to tell their client what he wanted to hear, but even they couldn’t provide Trump with proof that doesn’t exist. The same is true of state-based audits, which confirmed that the actual election results from that race were accurate.

Now, the president has reportedly hired a lawyer to oversee yet another investigation, apparently because the original probes, including the ones he paid for, were too reality-based for him.

Whether Olson will be paid with public funds is not yet clear. Watch this space.

This post updates our related earlier coverage.

Steve Benen is a producer for “The Rachel Maddow Show,” the editor of MaddowBlog and an MSNBC political contributor. He’s also the bestselling author of “Ministry of Truth: Democracy, Reality, and the Republicans’ War on the Recent Past.”

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