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As Trump prosecutes more adversaries, some allies see trouble getting convictions

Oct 8, 2025, 5:29pm EDT
Politics
President Donald Trump
Evelyn Hockstein/Reuters
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The News

President Donald Trump expects the Justice Department to not just indict, but convict his political adversaries — with more targets to come.

Some of his allies are keeping expectations in check.

Take former FBI Director James Comey, who pleaded “not guilty” Wednesday to charges of lying to Congress that are pending in the Eastern District of Virginia. That area contains most of the state’s Democratic cities and suburbs, which left Senate Judiciary Chair Chuck Grassley skeptical that Comey could be convicted.

“I only say this from a standpoint of knowing what this area thinks,” the Iowa Republican told Semafor, pointing to past failed prosecutions in the DC area by Trump-appointed special counsel John Durham. “I think it’s difficult to get a consensus that’s not very pro-Democratic. So it’d be very difficult.”

Three other Trump enemies have yet to be charged in ongoing DOJ investigations: New York Attorney General Letitia James, Federal Reserve Board Governor Lisa Cook, and California Sen. Adam Schiff. All are accused of mortgage fraud by the Trump administration, a charge that can be difficult to prosecute.

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Add former Trump national security adviser John Bolton, Obama-era CIA director John Brennan, and Obama-era Director of National Intelligence James Clapper to the list of those being scrutinized by federal prosecutors this year, and the roster of Trump targets grows dizzyingly long. So it’s notable that the president’s party is dubious about convicting Comey, the first test case whose indictment many Republicans cheered.

“Trump spent how many days in a courtroom, and [they] raided his house — I think he probably wants to see all these people suffer as much as humanly possible,” one person close to the White House said of those who investigated Trump during various probes since his first campaign.

“But it’s also Virginia,” the person added. “I think it’s going to be very, very difficult to get anything like [a conviction].”

The ranks of Trump enemies with legal blowback could soon include former DOJ special counsel Jack Smith. He faces a probe from the Office of Special Counsel and new scrutiny after Grassley released an FBI document showing GOP lawmakers’ phones were reviewed during Smith’s investigation into the Jan. 6 Capitol riot.

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There’s no denying the prosecutions, which Democrats and members of the legal establishment have denounced as outrageous abuses of power, are personal for Trump. The exception, perhaps, is Cook, whose mortgage fraud allegations are providing the administration’s rationale for seeking to oust her from the central bank.

The president threw two more names on his list Wednesday, saying he wants Chicago Mayor Brandon Johnson and Illinois Gov. JB Pritzker jailed for not protecting immigration agents during protests.

Trump and his allies, regardless of how they view the cases, strongly believe crimes were committed. Some also acknowledge that retribution is a key motivation.

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“I actually think they did commit these crimes, and the evidence is there,” the person close to the White House told Semafor. “[But] if they weren’t trying to go after Trump, would he be digging up shit on them? Probably not.”

The White House and Federal Housing Finance Authority, whose director initiated the mortgage fraud investigations into Cook, James, and Schiff, referred Semafor to the DOJ. The DOJ declined to comment.

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Know More

FHFA Director Bill Pulte, a former private equity executive, has accused the trio of engaging in mortgage fraud by inaccurately describing properties as primary residences. But allegations of mortgage fraud are particularly hard to prosecute, in part because the government has to prove the fraud was conducted intentionally.

The administration is already hitting that wall in its case against James; less than a month after Trump forced out US Attorney Erik Siebert for failing to uncover sufficient evidence, MSNBC reported that another top prosecutor in the state has told colleagues she does not see probable cause either.

Particularly if the mortgage applicant discloses their plans to their lender, “they’re incredibly hard cases to prove,” said economist Dean Baker, a cofounder of the progressive-leaning Center for Economic and Policy Research who has written about the mortgage fraud allegations against Cook.

Schiff reportedly told his lender he planned to describe two properties as primary residences because — as a member of Congress who commutes to Washington — he planned to reside in both. He’s even said he consulted with House legal advisers.

“You have to show that he intended to deceive them,” Baker said. “And if he had told them exactly the situation — it doesn’t matter what box he checked.”

Muddying the waters further: Subsequent reporting that a trio of Cabinet members and even Pulte’s own relatives may have made similar missteps.

Sen. John Kennedy, R-La., a member of the Judiciary Committee, said housing regulators “have not done a very good job of enforcing the law. But if you start enforcing it for some, you’ve got to enforce it for all.”

The Supreme Court will hear oral arguments on Trump’s overarching attempt to fire Cook in January.

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Room for Disagreement

Despite the high hurdles, some Republicans want the DOJ to try to add further charges to the Comey prosecution.

“What you’re going to see, I hope, is further investigation, ultimately indictments on this conspiracy against the United States, conspiracy against rights that originated with the Russiagate hoax,” said Sen. Eric Schmitt, R-Mo., a former state attorney general.

“So whether it’s Comey, Clapper, Brennan and probably a whole host of other folks that perpetrated this effort, I think that’s where the indictments are coming,” he added.

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The View From Democrats

“The real tragedy is that these cases were brought in the first place,” North Carolina Rep. Deborah Ross, an attorney who serves on the House Judiciary Committee, told Semafor.

“It’s very difficult to get a conviction, and that’s why you have to trust the judgment of career prosecutors, the people who the Trump administration has fired — and not hacks, the people who the Trump administration has hired,” she added.

Still, Democrats have learned to take Trump’s legal threats far more seriously this term. Senate Minority Whip Dick Durbin, D-Ill., said he isn’t laughing off Trump’s threats to jail his home-state colleagues.

“What he’s done is outrageous, certainly, when it comes to Sen. Schiff and others. I don’t put anything past him,” Durbin said.

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Notable

  • Pulte allegedly circumvented the FHFA’s inspector general in pushing a criminal referral for Cook, Reuters reported.
  • A key witness against Comey was allegedly found to be “problematic” by prosecutors involved in the investigation, according to ABC News.
  • Mike Davis, a conservative lawyer and key Trump ally, told Steve Bannon that even if Comey isn’t convicted, he wants “the process to be the punishment.”



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