Donald Trump’s legal battles have followed him through two presidencies, with several disputes continuing to generate headlines long after the original court proceedings ended.

Among the most expensive is his ongoing conflict with writer E. Jean Carroll, who successfully sued the president over statements he made about her allegations of sexual abuse.

The case resulted in a massive financial judgment against Trump, but the president has continued fighting the outcome through the federal court system. His legal team now hopes the country’s highest court will provide a way out.

According to RadarOnline, Trump’s attorneys are once again asking the US Supreme Court to intervene in the defamation case, arguing that his status as president should protect him from personal financial liability for statements made while he was in office.

The amount at stake is hardly insignificant.

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Trump is attempting to overturn an $83.3 million judgment, while Carroll’s lawyers argue that his latest legal strategy comes years too late.

Trump turns to presidential immunity

The dispute centers on comments Trump made about Carroll while serving his first presidential term.

Carroll accused Trump of sexually assaulting her in a department store during the 1990s, an allegation she publicly discussed in her memoir, What Do We Need Men For?: A Modest Proposal.

Trump denied the accusation and publicly attacked Carroll’s credibility.

He suggested that she had fabricated the allegation to attract attention and promote her book.

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Carroll subsequently brought a defamation lawsuit, arguing that Trump’s statements had damaged her reputation.

A federal jury eventually awarded her $83.3 million in damages.

Trump has repeatedly challenged the verdict, and his latest appeal focuses on whether the presidency should shield him from civil liability for the statements at issue.

His lawyers argue that the comments were made during his time in the White House and should therefore fall under presidential immunity.

The petition describes the judgment as “the first case in our Nation’s history in which a court has imposed damages liability on a President for his conduct in office.”

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Trump’s attorneys maintain that the dispute raises important constitutional questions extending beyond the financial consequences for their client.

Their central argument is that allowing the judgment to stand could expose future presidents to personal lawsuits over statements made while performing official duties.

Carroll’s legal team, however, strongly disputes that interpretation.

Carroll’s lawyers say Trump abandoned his own defense

The latest disagreement concerns not only whether presidential immunity could apply but also whether Trump waited too long to invoke it.

In a response filed Friday, Carroll’s attorneys argued that the president had effectively surrendered the defense during the early stages of litigation.

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According to their filing, Trump initially told the court that Carroll could pursue her lawsuit after he left office.

Her lawyers contend that this position amounted to a deliberate decision not to claim absolute presidential immunity.

They wrote that the “petitioner chose to renounce that defense at the outset of this case.”

The filing also pointed to an earlier letter in which Trump’s legal team reportedly stated that Carroll was “free to pursue this action when the President is no longer in office.”

At the time, Trump’s attorneys also maintained that he was not attempting to “escape accountability.”

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Carroll’s lawyers argue that those earlier statements are difficult to reconcile with his current insistence that presidential immunity should prevent the judgment from being enforced.

Their position is that Trump cannot spend years contesting a lawsuit and then seek to overturn the result through an immunity argument he previously declined to pursue.

The timing could become Trump’s biggest obstacle

The legal disagreement has become particularly focused on the procedural history of the case.

According to Carroll’s attorneys, Trump actively participated in the litigation for several years before attempting to introduce presidential immunity as a defense.

Their filing states:

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“Over the ensuing years, petitioner repeatedly affirmed his waiver of immunity by actively litigating this case. Even when he eventually raised presidential immunity – three years into this litigation – he did not raise the question the petition presents that there is some sort of heightened standard for waiving presidential immunity.”

The lawyers continued:

“That argument didn’t come until another two years later, at which point the Second Circuit held it was too late.”

The distinction is significant.

Trump’s latest petition asks the Supreme Court to consider whether a president must satisfy a particularly demanding legal standard before being considered to have waived immunity.

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Carroll’s attorneys argue that the question does not need to be addressed because Trump repeatedly chose not to rely on the defense when he had the opportunity.

Their argument is therefore less about the broad constitutional limits of presidential immunity and more about the procedural decisions Trump made during the litigation.

For the president, that could represent a substantial obstacle.

A dispute that could affect future presidents

Trump’s legal team has attempted to present the case as a matter of constitutional importance rather than simply a disagreement over damages.

In a petition filed in July, his attorneys argued that the judgment could fundamentally alter the legal protections available to future occupants of the White House.

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Their concern is that presidents could face personal financial liability for communications made while carrying out their official responsibilities.

The argument draws on the longstanding principle that presidents enjoy certain protections from civil lawsuits involving official conduct.

However, presidential immunity is not unlimited, and whether particular statements qualify as official acts can be a separate legal question.

Carroll’s lawyers maintain that the Supreme Court does not need to resolve those broader issues in this case.

They argue that Trump’s earlier litigation decisions provide sufficient grounds for rejecting his appeal.

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The filing also emphasizes that previous presidents who wanted to invoke immunity generally did so at the beginning of legal proceedings.

“For a half century at least, every President who has wanted to raise presidential immunity has done so at the outset of litigation,” Carroll’s lawyers wrote.

They added:

“Indeed, this President has raised absolute immunity in the first pleading in other cases against him.”

The attorneys argue that Trump’s experience with immunity claims in other lawsuits makes his handling of the Carroll litigation particularly difficult to justify.

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Supreme Court faces another request from Trump

The latest petition comes after Trump has already encountered setbacks in his efforts to challenge the Carroll judgment.

His attorneys are now asking the Supreme Court to revisit the dispute and consider the constitutional arguments they believe lower courts failed to address adequately.

However, the justices are not required to hear the case.

The Supreme Court receives thousands of petitions annually and accepts only a small proportion for full review.

Carroll’s lawyers are urging the court to decline Trump’s request without proceeding to a broader examination of presidential immunity.

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Their filing states:

“So the question of exactly how explicit a President must be to waive immunity does not warrant certiorari.”

Certiorari is the legal mechanism through which the Supreme Court agrees to review a lower court’s decision.

The attorneys conclude with a direct request.

“This Court should deny review. There is no good reason for this Court to overlook the many procedural obstacles presented by this case.”

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Their argument is that Trump’s appeal presents no compelling reason for the justices to intervene.