F inding that presumptive Republican presidential nominee Donald Trump’s own dilatory tactics are the cause of the financial squeeze in which he now finds himself, a Manhattan federal court declined on Thursday to exercise whatever discretion it might have to give him a few extra days to arrange an approximately $90 million bond.
Trump will need such a bond to block enforcement of the $83.3 million judgment in the E. Jean Carroll defamation case. That judgment will become final on Monday, March 11. That is, unless Trump arranges a bond in the next three days, Carroll may begin enforcement actions to make him pay.
The unsubtle message of the one-page memorandum denying Trump’s application, issued on Thursday by Southern District of New York (SDNY) judge Lewis Kaplan, is: Quit stalling and get the bond. (The “memorandum endorsement” is here, attached to the first page of the letter brief by which Trump’s counsel, Alina Habba, made the application.)
While that message is simple, the background is a bit complicated (as I’ve previously related here, here and here).
On January 26, 2024, after a two-week civil trial, the jury found Trump liable for Carroll’s two remaining claims of defamation, stemming from statements made by Trump in 2019 and 2023. This was the Carroll II trial. Last year, in the Carroll I trial, a jury found Trump liable on civil claims of (a) sexual abuse, stemming from an incident Carroll claims occurred in the mid Nineties, and (b) defamation, stemming from statements made by Trump in 2022.
While the first jury awarded the journalist comparatively modest damages, totaling $5 million ($2.02 million for sexual abuse and $2.98 million for defamation), the jury in Carroll II slammed Trump with a stunning $83.3 million verdict — combining compensatory damages ($7.3 million), a reputation-rehabilitation fund ($11 million), and punitive damages ($65 million).
I do not mean to disparage Carroll, who was an effective witness in describing a nearly 30-year-old incident of alleged sexual assault for which there is scant corroboration. Still, the verdicts were also driven by a combination of Trump’s strategic blunders and Kaplan’s controversial rulings.
Trump decided to neither attend nor testify at the first trial, despite having every opportunity to do so, making it highly likely that the civil jury would find him liable (as it did). Kaplan permitted devastating similar-act evidence unrelated to the alleged assault against Carroll — specifically, testimony from two other women who claim to have been victims of Trump’s sexual aggression (though the incidents they describe are not as severe as the Carroll allegation), plus the infamous Access Hollywood tape in which Trump is heard to brag about being sexually aggressive with women.
In the second trial, Trump attended and insisted he wanted to testify to refute the allegations against him (as he has always done publicly and stridently — hence, the defamation claims). Kaplan, however, ruled that the rape and defamation issues had already been settled in the first trial; Trump was not permitted to deny the allegations and his testimony was drastically curtailed under Kaplan’s micromanagement. In essence, the trial was reduced to a question of how much the jury would demand that Trump pay Carroll.
Obviously, there are significant appellate issues. That’s not to say Trump will necessarily prevail in getting the verdicts reversed or the monetary damages materially reduced, just that the appeals will not be frivolous. Trump’s appeal of the first judgment is already pending.
In federal law, enforcement of a judgment is delayed (or “stayed”) for 30 days after the judgment is final. In Carroll II, the judgment became final on February 8, when the SDNY docketed the court’s recording of the jury’s January 26 verdict. Consequently, if no further stay is ordered, Carroll could begin action to enforce the judgment on March 11. (The 30th day after February 8 is March 10; but that is a Sunday, so the law extends the deadline to the following business day, Monday, March 11.)
Enforcement of a judgment can be delayed while the court considers posttrial motions and, if those motions are denied, while the case is on appeal. But the stay on enforcement is not automatic after the first 30 days. Instead, the defendant is generally expected to place the amount of the judgment, plus interest, in escrow with the court — by either paying cash or posting a bond (or some combination of the two).
If Trump’s only financial problem were the Carroll II judgment, he could probably just post a bond. Analysts who follow these matters have estimated that he is a billionaire (worth about $2.6 billion according to Forbes in 2023 — i.e., before the lawfare campaign started to bite) and that he has roughly $400 million in liquid assets in addition to significant real-estate holdings (that are heavily leveraged and thus could be complicated to post as collateral for a bond).
Yet, Carroll II is far from the only strain on Trump’s finances. Of most consequence, on February 16, in New York attorney general Letitia James’s civil fraud lawsuit against the former president, Judge Arthur Engoron found him liable for a staggering $454 million ($355 million in “disgorgement” damages, plus over $98 million in pre-judgment interest). Interest is accruing on that judgment at a rate of $112,000 per day. Trump is appealing it; if he wants to stay enforcement of it while the appeal is pending, he will need to post a bond of roughly $500 million.
Moreover, Trump has significant business loans coming due this year — around $250 million worth according to a 2021 Forbes estimate. Assuming he needs to renegotiate some or all of these loans, that may be challenging — even if the real-estate and other assets already pledged as collateral can cover such loans — because of (a) these civil judgments and (b) the possibility that he could face criminal convictions and potential imprisonment stemming from the four pending indictments against him. (Of course, he could also be elected president of the United States come November — go figure.)
Manifestly, the financing of a $90 million bond in Carroll II complicates, and is complicated by, Trump’s need to cover a bond in the civil fraud case, as well as his other debts.
Trump waited until February 23 (25 days after the jury verdict) to ask Judge Kaplan to stay enforcement of the Carroll II judgment pending the court’s decision on his posttrial motions, which he did not file until March 6 (this past Tuesday). Despite the usual obligation to post a bond in the judgment amount (plus interest) to obtain a stay, Trump did not offer any bond. Rather, knowing that the judgment would become final on March 11 and that more time would be needed to arrange a $90 million bond, Trump asked Kaplan to rule on his stay motion by March 4 (i.e., this past Monday).
Alternatively, if Kaplan could not (or did not) rule on the stay pending decision on the posttrial motions by Monday, Trump asked that he grant a “temporary administrative stay.” The idea was to block enforcement of the $83.3 million judgment while Kaplan takes whatever time he needs to decide whether to delay enforcement as he considers the posttrial motions (that, as noted above, were just filed two days ago).
These proposals regarding an “administrative stay” are what Kaplan rebuffed in his short memorandum yesterday.
The judge cast doubt on the legal viability of so-called administrative stays. The concept of an “administrative” stay dubiously assumes that courts have supervisory authority over their own proceedings, which empowers them to issue stays beyond the statutorily based Federal Rules of Civil Procedure (here, Rule 62). Nevertheless, although he assumed for argument’s sake that he had the authority to issue a brief administrative stay in appropriate circumstances, Kaplan denied to do so in this case.
The judge reasoned that “Mr. Trump’s current situation is a result of his own dilatory actions.” On that score, Kaplan cited Trump’s nearly four weeks of foot-dragging before finally seeking an unsecured stay (which Trump amended this past weekend, offering to post $24.4 million, less than a third of the judgment amount). Kaplan concluded that, even though he had ordered expedited briefing to try to resolve the stay issue quickly, there was not sufficient time for deliberation and decision prior to the lapsing of Rule 62’s automatic stay, solely because of Trump’s brinksmanship.
Bottom line: If Trump wants a stay, he has to pay.
One last point: While Kaplan does not mention it in his memorandum, one of the things Trump has done since January 26, instead of arranging a bond, was suggest that the judge should be disqualified based on a supposedly undisclosed close professional relationship with Carroll’s top lawyer. That lawyer, Roberta Kaplan (no relation), vigorously denied the flimsily supported claim posited by Habba, Trump’s lawyer, who then dropped the matter.
Trump’s gambit was part of a political strategy to paint each component of the lawfare campaign against him as partisan persecution. (Lewis Kaplan is a Clinton appointee; Roberta Kaplan is a Democratic activist.) But while there is considerable evidence of self-serving Democratic scheming behind the array of civil and criminal lawsuits lodged against Trump, there is no meaningful evidence supporting the ethical-misconduct claims Trump’s team slyly hinted at (“just asking questions here”) without expressly raising.
However effective that may have been as a political strategy, it is a boneheaded legal strategy to offend the judge when — as in the matter of the stay, which Trump badly needs — one is asking for indulgence that the judge is not required to give.
In any event, Trump will need to secure a bond of around $90 million by Monday if he wants to block enforcement action by Carroll. How that may affect his capacity to secure the $500 million bond he’ll need by March 25 to block enforcement of the civil fraud judgment is impossible to predict — except to say, it sure won’t help.