In the political world, Donald J. Trump is on the cusp of something that eluded him in 2016: a clear victory in the Iowa caucuses this month. His advisers hope it will be the first in a series of early state victories that propel him to collect enough delegates to be the presumptive Republican presidential nominee by late March.
In the legal world, however, the former president is at the same time facing two trials this month that hit on a deeply personal level. One is the wrap-up of the New York attorney general’s civil fraud case against him and his company and an expected decision from the judge on the penalties he must pay. The other is the damages trial for defaming E. Jean Carroll, a New York writer who said he raped her in a New York department store in the 1990s. A jury last year said he had sexually abused her.
It is a juxtaposition that Mr. Trump has so far managed to his advantage on the campaign trail, casting himself as the victim of political and legal persecution by a Democratic establishment out to silence him and his supporters. In both trials, he could face substantial financial penalties and a significant change in how — or if, in a worst-case scenario for him — he continues to control his business.
If Mr. Trump has helped himself in court with his methods, it has been hard to discern so far, given how the judges have engaged with him and his arguments. Yet, in the face of this political-legal collision, he considers himself his own best defender and communicator, and in 2024, what the court of Republican public opinion will tolerate is different from what a court of law will allow.
Mr. Trump is among the most disciplined undisciplined political figures in modern U.S. history: For all his self-inflicted wounds in his public comments and erratic social media posts, he is fairly rigid in delivering a repetitive message of grievance and victimization to his followers. He is aiming to turn undesirable circumstances that he’s furious about into a kind of high-stakes drama that he can direct as he and his campaign navigate a thicket of legal proceedings in the coming months.
Mr. Trump, who attended much of the civil fraud trial, said on Tuesday that he planned to attend that trial’s final stage as well as the Carroll trial.
That will have him flying back and forth from New York to Iowa and New Hampshire to juggle days of planned campaign events. He is also making plans to attend next week’s federal appeals court arguments in Washington on his claims that he should have presidential immunity in his federal election fraud trial, according to three people with knowledge of the matter.
It’s a court appearance that promises to be a unique media spectacle in the nation’s capital, and will fall just days after the anniversary of Jan. 6, when a pro-Trump mob swarmed the Capitol building during certification of his 2020 election loss.
While Mr. Trump is facing 91 criminal charges in four different jurisdictions, the case in which he and his company have been found to have committed decades-long fraud is taking place more immediately, and cuts to the heart of his business brand. That case, overseen by Justice Arthur Engoron, and the one brought by Ms. Carroll have enraged him for months, according to people who have spoken with him.
Mr. Trump, who contacted The New York Times after learning an article was being written about the legal actions unfolding in January alongside the first rounds of voting, described the cases in a phone interview as “unfair.”
He criticized the judges in both trials, describing Judge Lewis Kaplan, the federal judge who is overseeing the Carroll case, as “more radical” than Justice Engoron, who issued a partial summary judgment against Mr. Trump before the trial began, leaving just a half-dozen claims left to be ruled on, along with penalties. Mr. Trump again highlighted comments the attorney general made targeting him during her 2018 campaign for her post.
He also said there was a case scheduled just before “every election.” The federal trial he faces on charges of conspiracy to defraud the United States is set to start on March 4, the day before Super Tuesday, although it is widely expected to be delayed.
The former president said he planned to attend the remaining day of closing arguments in the case before Justice Engoron, and said he wanted to testify in the Carroll case — something he didn’t do during the first trial, and which he made clear in the brief interview that he regretted. He said he had been talked out of it last time.
“I’m going to testify,” Mr. Trump said, something that his advisers are not uniformly behind.
The Iowa caucuses are on Jan. 15. His team is set to leave straight for New Hampshire from Iowa on Jan. 16, the same day the Carroll case begins, and it remains to be seen if that changes.
Last year, a jury in a civil trial in a separate case brought by Ms. Carroll found that he had sexually abused her and defamed her in a Truth Social post in late 2022. Mr. Trump continues to rail against the case, which a federal appeals court declined to delay in a decision last week. He has insisted that Justice Engoron has been biased, and has attacked him and his law clerk.
The Trump team sees the civil and criminal cases against him as part of a vast conspiracy led by President Biden to thwart his camp, without offering evidence for their claims. They are suspicious of the timing of the Carroll trial, falling the day after the Iowa caucuses in a Manhattan federal courthouse and seven days before the New Hampshire primary. They repeatedly note that Ms. Carroll’s earlier suit was helped financially by the Democratic donor Reid Hoffman.
“This is unequivocally a concerted effort to attack President Trump during the height of his political campaign,” said Alina Habba, one of Mr. Trump’s lawyers in both cases.
A spokeswoman for Ms. Carroll said that “regardless of whether Donald Trump shows up at the trial in two weeks, E. Jean Carroll looks forward to presenting her case to a jury whose only job will be to determine how much in additional damages she will be entitled to receive.”
David Kochel, a Republican strategist who has been opposed to Mr. Trump, said that mixing his court appearances with his campaign has been, in the Republican primary, successful for him so far, and it’s not surprising he would seek to make the most politically of a problematic month.
“It keeps him in the center of the spotlight,” Mr. Kochel said. “It builds into his argument that he is a victim, that he’s constantly being targeted, that this is election interference and all that, so it makes sense to me to be going back and forth because the legal stuff is part of his campaign strategy now, and fund-raising. It’s worked for him throughout this entire process.”
It will also keep him in the news — and potentially deprive his Republican primary rivals of oxygen — at a time when the voting is beginning, Mr. Kochel said, adding, “He’s the executive producer of all of this.”
But the short-term victories around the civil trials do not necessarily add up to longer-term gains in a general election, said Dan Pfeiffer, a Democratic strategist and former top adviser to former President Barack Obama.
“Trump is always a ‘deal with the challenges right in front of him right now and then deal with the consequences later’” person, Mr. Pfeiffer said. “This has a cost to him, because — and all the polling shows this — most Americans have paid almost no attention to all of Trump’s cases and they will start to pay more attention.”
He added, “Shining a spotlight on his greatest general election vulnerabilities just as the general election electorate wakes up is a high-risk strategy.”