U.S. District Judge Lewis Kaplan issued an order on July 4 directing Donald Trump to release a $5.8 million civil judgment held in escrow to E. Jean Carroll by the following Tuesday, or explain to the court why he would not. The order came as Carroll's legal team raised alarms about a separate maneuver they say could threaten not just that payment, but the far larger $83.3 million defamation award a Manhattan jury handed Carroll in 2024.
The maneuver in question: a letter Trump's former attorney Justin Smith sent to the U.S. Supreme Court suggesting the justices "may wish to consider the petitions together," given that both cases involve the same parties. Carroll's attorneys say the move is designed to buy time and could ultimately result in both judgments being wiped out.
For anyone who has watched the Carroll litigation drag on for years, through two separate trials, two separate verdicts, and an ever-expanding menu of post-trial motions, the latest chapter raises a straightforward question. Is this a legitimate legal strategy, or is it a procedural stalling tactic dressed up in Supreme Court letterhead?
The $5.8 million judgment has been sitting in escrow. Judge Kaplan's July 4 order set a hard deadline: release the funds to Carroll or tell the court why not. That order, as reported by Alternet, came after Carroll's attorneys accused Trump's side of seeking yet another extension, one they characterized as a delay play.
Carroll's attorney Roberta Kaplan, no relation to the judge, wrote to the court with a pointed accusation:
"We can only assume that defendant is seeking... to buy time so he can try to concoct some new basis to put off paying plaintiff presumably in connection with his forthcoming petition and motion for a rehearing."
Carroll's lawyers went further, calling Trump's extension request "little more than yet another play for time."
Strong words. But the underlying facts are worth separating from the advocacy. Trump's legal team has not publicly conceded any intent to delay. And the question of whether two related cases involving the same plaintiff and defendant should be considered together at the Supreme Court level is not, on its face, an unreasonable legal position.
The two Carroll judgments emerged from separate proceedings. The $5.8 million award came first. The $83.3 million defamation verdict followed in 2024 from a Manhattan civil jury. Trump has publicly contested both, and an appeals court has already delayed payment of the larger judgment pending Supreme Court review.
Justin Smith, described as Trump's former attorney, wrote to the Supreme Court in what was characterized as "one of his final acts" in that role. His argument: since both petitions involve the same parties, the Court might benefit from reviewing them in tandem. Whether the justices take that suggestion seriously, or ignore it entirely, remains to be seen.
Carroll's team fears the worst-case scenario. If the Supreme Court agrees to consider both cases together, the resulting delay could give Trump's lawyers room to raise new arguments, including presidential immunity, that might jeopardize both awards. That fear, at least, is what Carroll's attorneys have put on the record.
Trump himself has never been shy about his opinion of these cases. In a 2023 Truth Social post, he laid into Judge Lewis Kaplan directly:
"What else can you expect from a Trump Hating, Clinton appointed judge, who went out of his way to make sure that the result was as negative as it could possible be, speaking to, and in control of, a jury from an anti-Trump area which is probably the worst place in the US for me to get a fair 'trial'."
That post captures the core of Trump's position: he believes the venue, the judge, and the jury pool were stacked against him. Whether you agree with that assessment or not, it is the stated basis for his continued legal challenges. And it is worth noting that the Supreme Court has not yet weighed in on the merits of either case.
The broader question of presidential immunity hovers over the larger judgment. If the Supreme Court agrees to hear arguments on that front, the legal landscape could shift in ways Carroll's team clearly does not want to contemplate. Several pending Supreme Court cases already have the potential to reshape the legal terrain around Trump's second-term agenda.
Strip away the legal jargon and Carroll's lawyers are making a simple argument: Trump is running out the clock. They want the $5.8 million released now, before any Supreme Court action on the $83.3 million case can complicate matters. They fear that if the two cases get bundled together for review, a ruling favorable to Trump on one could drag the other down with it.
That concern is not frivolous. Courts do sometimes consolidate related cases, and when they do, the procedural timeline resets. For a plaintiff waiting on payment, consolidation is a nightmare. For a defendant contesting both verdicts, it is a lifeline.
But Carroll's team has its own credibility questions to manage. Carroll has denied perjury allegations after a reported DOJ probe sparked a public firestorm, a development that has given Trump's supporters additional ammunition to question the foundation of both verdicts.
Judge Kaplan's order puts the immediate pressure on Trump. Release the $5.8 million or explain yourself, by Tuesday. That is a tight window, and it forces Trump's current legal team to make a concrete decision rather than let the escrow sit indefinitely.
What happens next depends on several moving parts. Will Trump's team comply, contest, or seek yet another extension? Will the Supreme Court take any interest in Smith's suggestion to consolidate? And will the question of presidential immunity, a live issue in multiple Trump-related proceedings, reach the Carroll cases at all?
The dynamics at the Supreme Court itself remain fluid. Internal tensions among the justices and their allies over Trump-era legal battles add another layer of uncertainty to any prediction about how the Court will handle these petitions.
Carroll's attorneys want to frame every procedural move by Trump as bad faith. That is their job. But the legal system exists precisely so that defendants, even unpopular ones, even sitting presidents, can exhaust their appellate options before paying out millions. The right to appeal is not a delay tactic. It is a constitutional safeguard.
Whether Trump's team is using that right strategically or abusing it is a judgment call that ultimately belongs to the courts, not to opposing counsel's press-ready letters. Judge Kaplan has set a deadline. The Supreme Court has its own timeline. The system will produce an answer.
The real question is whether the legal institutions handling these cases will apply the same procedural fairness to Trump that any other litigant would receive, no more, no less. Recent Supreme Court decisions in other Trump-era cases suggest the justices are not inclined to rubber-stamp every claim that lands on their docket, but neither are they ignoring legitimate constitutional questions.
Carroll's team wants its money. Trump's team wants its day in court. Only one of those positions requires the other side to stop fighting. In America, that is not how the law is supposed to work.