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Trump's aggressive legal strategies keep backfiring spectacularly
His lawyers love using the courtroom for political attacks. It's not going well.
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Even before he was president, Donald Trump had a reputation for engaging in vindictive litigation and stiffing his lawyers. Since leaving the White House, he’s been able to feed his habit by tapping an infinite stream of donor cash from his PACs to pay his legal fees. Trump has filed clownsuit after performative clownsuit even as his aggressive courtroom posture regularly comes back around to bite him, as it did at least at least three times in the past two weeks.
He sued social media platforms and CNN for violating his First Amendment rights. He sued New York Attorney General Letitia James in Florida state court for maliciously prosecuting him in New York. He sued the Pulitzer Prize Board (housed at Columbia University) in the Circuit Court for Okeechobee County for defamatory refusal to revoke the 2018 prizes awarded to the New York Times and Washington Post. And he sued Hillary Clinton and her BFF James Comey for civil RICO, on the theory that they conspired with half of DC to gin up a fake FBI investigation into his campaign’s ties to Russia.
That last one resulted in a million dollars in sanctions against Trump and his lawyers for dragging dozens of individuals with no connection to the state into a federal court in Florida, forcing them to hire local counsel to defend them against his preposterous claims.
In his dismissal order, US District Judge Donald Middlebrooks cited “Mr. Trump’s pattern of misusing the courts to serve political purposes.” He laid out the Trump legal “playbook,” consisting of “Provocative and boastful rhetoric; A political narrative carried over from rallies; Attacks on political opponents and the news media; Disregard for legal principles and precedent; and Fundraising and payments to lawyers from political action committees.”
A rational person might interpret this as a warning that the federal judiciary was on to him and tread more cautiously in the future. But no one has ever accused Trump of being a rational person, and indeed he’s continued pedal to the metal, suing his former attorney Michael Cohen for defamation, reporter Bob Woodward and Simon & Schuster for turning his rants into an audiobook, and the Washington Post for defamation via his eponymous TMTG media “empire.”
PR spin is not a legal plan
Trump’s lawyers, taking their cue from their client, approach each case in a maximally aggressive posture, even as it weakens their client’s case. Nowhere was that more apparent than in the E. Jean Carroll defamation suits, where Trump attorneys Alina Habba and Joseph Tacopina managed to infuriate Judge Lewis Kaplan with their constant dilatory tactics, accusations of bad faith by opposing counsel, and procedurally defective filings.
Carroll, an advice columnist, filed Carroll I in 2019 after Trump denied her account of being sexually assaulted by him in the mid-1990s, accusing her of fabricating the allegation in cahoots with his political opponents. That case was temporarily derailed by a dispute over whether Trump was acting within the scope of his official duties as president when he made the 2019 statement. In the meantime, New York passed its Adult Survivors Act, granting a one-year amnesty for sexual abuse tort claims which would otherwise be time-barred. And all the while, Trump continued to repeat the allegations about Carroll, including in an October 2022 statement on Truth Social which, along with sexual abuse claim under the ASA, formed the basis of Carroll II.
“We're in one sense gratified. I know some people in [Trump’s] camp are very happy that the rape claim was rejected,” Tacopina said on the courthouse steps. As a media talking point, it’s not terrible. But Trump and his lawyers consistently confuse PR strategy with a legal plan, so they actually filed multiple court filings seeking to gain advantage from the jury’s inability to determine if Trump managed to forcibly penetrate Carroll with his penis, or just his fingers.
The “I’m just a molester, not a rapist” argument (slight paraphrase!) has now made it into a counterclaim in Carroll I, in which Trump argues that the jury disbelieved Carroll’s story and thus she defamed him. Trump has also filed a motion for a new trial in Carroll II, on the theory that the jury must have been confused when it awarded Carroll $2 million for sexual abuse which could have amounted to no more than “groping of [Carroll’s] breasts through clothing or similar conduct, which is a far cry from rape.”
To put it in layman’s terms, this is like the famous Sideshow Bob “attempted chemistry” argument, only in court as opposed to on a jailhouse payphone. And while the Carroll I counterclaim is still pending, Judge Kaplan already penned a furious order denying Trump’s motion for a new trial and branding him a digital rapist.
The jury’s finding of sexual abuse therefore necessarily implies that it found that Mr. Trump forcibly penetrated her vagina. And since the jury’s answer to Question 1 demonstrates that it was unconvinced that there was penile penetration, the only remaining conclusion is that it found that Mr. Trump forcibly penetrated her vagina with his fingers – in other words, that he “raped” her in the sense of that term broader than the New York Penal Law definition.
The trial evidence of the harm to Ms. Carroll as a result of being assaulted and digitally raped supports the jury’s $2 million award as reasonable compensation for her pain and suffering.
So, not only did Trump not get himself a new trial, but he set fire to his own PR strategy by baiting the court to issue a judicial finding that Trump is a rapist, at least within the colloquial sense of the word.
Trump walks right into it in the Southern District
Trump scored another own goal in the Southern District of New York with his effort to remove the prosecution by Manhattan District Attorney Alvin Bragg to federal court. DA Bragg indicted Trump in April on 34 counts of falsifying business records to cover up the 2016 hush money payment to Stormy Daniels. Trump argued that he was acting in his official presidential duty when he signed personal and business checks to reimburse Michael Cohen for the money he fronted, and thus the case should be removed from New York state court.
The checks were falsely denominated as payments under a retainer agreement, and Trump’s lawyers argued in their removal notice that Cohen was actually performing legal work to segregate Trump’s personal assets so as to comply with the Emoluments Clause.
In the event, this allowed US District Judge Alvin Hellerstein to make a finding of fact that Cohen was not performing legal work for Trump during 2017 — decimating one of Trump’s putative defenses in the case.
In January 2017, Cohen and the Trump Organization CFO met to discuss how to reimburse Cohen. They agreed that Trump would pay Cohen $420,000 — $180,000 to reflect reimbursement for Cohen's $130,000 payment to Clifford's attorney and an additional $50,000 expense, doubled to $360,000 to enable Cohen to treat the reimbursement as income rather than reimbursement of a hush money payment, and an additional $60,000 bonus. Trump, Cohen, and the CFO then agreed that payment was to be made in monthly installments of $35,000 beginning January 2017. Cohen was to send an invoice monthly to the Trump Organization for payment pursuant to a "retainer agreement." The retainer agreement did not exist.
Similarly, the court order referred to a previously sealed exhibit containing “a handwritten notation by someone in the Trump Organization, likely the CFO, calculating how much Cohen was to be repaid for advancing the $130,000 payment to Stephanie Clifford [Stormy Daniels], and how the payment to him was to be disguised as income rather than reimbursement.”
So this little junket to federal court, which did not slow the prosecution down at all, produced nothing but judicial conclusions wholly unhelpful to Trump’s case.
A federal judge notices that Trump has plenty of time to be deposed
Trump’s shenanigans are even damaging him in cases to which he isn’t a party. To wit, former FBI official Peter Strzok is suing the Justice Department for wrongful termination and violation of his civil service protections. Strzok worked on both the Clinton email investigation and the investigation of the Trump campaign’s Russia ties, and was fired from the Mueller investigation for deriding Trump in personal texts with his colleague Lisa Page. After Deputy Attorney General Rod Rosenstein leaked the texts to reporters, Srzok and Page found themselves at the center of a right-wing conspiracy, with Trump tweeting constant calls for their dismissal.
Page resigned, but Strzok was eventually fired when Deputy Director David Bowdich overrode the recommendations of the bureau’s internal disciplinary officer that he receive a lesser penalty.
Strzok and Page both sued in 2019, and since then have been battling the DOJ to depose FBI Director Christopher Wray and Trump himself. Under the apex doctrine, plaintiffs must work their way up the ranks, deposing lower officers before they can gain access to the CEO or high government officials. Judge Amy Berman Jackson has thus forced Strzok to spend years in discovery, taking depositions of lower Trump DOJ officials, before finally greenlighting the depositions of Trump and Wray in February of this year.
The Justice Department has strong institutional priorities to protect the power of the executive, and so it has adamantly opposed allowing Strzok to take testimony of Donald Trump. But Judge Jackson was having none of it, noting earlier this month that Trump has plenty of time to spam federal and state dockets with doomed civil suits, so he can bloody well spare a couple of hours to explain what he meant when he publicly pressured the FBI to fire Strzok and then bragged about it post facto:
While to the extent the individuals deposed to date recalled the events in question, their testimony did not advance plaintiffs’ theory that the former President was involved in the decision making at issue in this case, the fact remains that the former President himself has publicly boasted of his involvement. Given the limited nature of the deposition that has been ordered, and the fact that the former President’s schedule appears to be able to accommodate other civil litigation that he has initiated, the outcome of the balancing required by the apex doctrine remains the same for all of the reasons previously stated.
Once again, Trump’s obnoxious courtroom antics and deluge of performative lawsuits have gotten him exactly where he didn’t want to be. And now, facing at least two criminal indictments, he shows no sign of slowing down.
That’s it for today
Aaron will be back tomorrow morning with a new podcast featuring comedian and political humorist Jay Black. If you’d like to support our work and aren’t already, please consider becoming a paid subscriber. Thanks!