Temidayo Aganga-Williams, a former federal prosecutor with the Brooklyn U.S. attorney’s office, said prosecutors likely welcome the possibilities created by Trump’s simultaneous indictments and civil proceedings.

“I would look at this as an opportunity,” said Aganga-Williams, who also served as senior investigative counsel for the House Jan. 6 select committee. “When you have a defendant that’s facing multiple cases, especially in multiple jurisdictions, there’s always opportunity for expanding your base of evidence.”

Take a recent dispute over a videotaped deposition that Trump gave as part of writer E. Jean Carroll’s lawsuit accusing him of rape and defamation.

On May 5, excerpts of that deposition became public after they were used as evidence during the trial (in which a jury sided with Carroll). Trump’s reactions to being questioned about Carroll’s accusations captured the attention of cable-news hosts and pundits across the country.

But they weren’t the only ones watching.

Across the street from the courthouse where the trial took place, prosecutors in the office of the Manhattan district attorney — who earlier this year brought the first-ever criminal charges against Trump — watched the deposition excerpts, too. And 10 days later, they subpoenaed the law firm representing Carroll in an effort to obtain the unreleased portions of the deposition, arguing in court filings that the full scope of his comments is relevant to their case, in which Trump is accused of falsifying business records to help cover up an affair with a porn star.

On Thursday, a judge ruled the law firm can comply with the subpoena.

Trump is facing a gauntlet of court dates over the next year at the same time that he is campaigning to return to the White House. He has five trials set to take place between October 2023 and May 2024: the Manhattan DA’s criminal trial, a federal criminal trial, a New York state civil fraud trial and two federal civil trials. A sixth trial in his newest criminal case — an indictment for trying to overturn the 2020 election — will be scheduled later this month. And he might soon face additional criminal charges in Fulton County, Georgia.

With so many deadlines, scheduling in one matter is likely to affect scheduling in another simply due to the sheer volume of activity — legal filings, discovery production, court appearances — set to take place within a limited amount of time.

But it is also Trump’s actions in and out of court in certain cases that have begun to prompt steps in others.

Earlier this year, for example, as the Manhattan indictment loomed, Trump encouraged his supporters to protest. In part as a result of Trump’s reaction to the threat of indictment, the judge overseeing the Carroll lawsuit ordered that the jury in that case remain anonymous, with their identities shielded from even the plaintiff and defense lawyers.

In his order, U.S. District Judge Lewis Kaplan cited “a very strong risk that jurors will fear harassment” while the Carroll trial proceeded as a result of Trump’s behavior in connection with the pending indictment.

Later, in the Manhattan criminal case, prosecutors asked the presiding judge for a so-called protective order to maintain the confidentiality of certain evidence. And in doing so, they cited two other Trump legal entanglements: the federal investigation into his handling of classified documents (for which he has since been indicted) and his civil lawsuit against his former lawyer Michael Cohen.

They told a judge that the documents investigation “gives rise to significant concern that Defendant will similarly misuse grand jury and other sensitive materials here.” And they argued that Trump’s lawsuit against Cohen (who is a key witness in the Manhattan case) “heightens the risk” that Trump will use the confidential materials “for purposes other than a defense of this case” — suggesting he might deploy them against Cohen.

And in an argument that went full-circle, the prosecutors also pointed out, in arguing that the protective order should delay the disclosure of the identities of certain district attorney’s office personnel, that the judge in the Carroll trial had taken the usual step of ordering that the jury be kept anonymous.

The judge overseeing the Manhattan criminal case ultimately issued a protective order that precludes Trump from publicly sharing discovery materials and limits his ability to view certain materials.

In certain instances, Trump appears to have attempted to take advantage of scheduling issues in his multiple cases.

In March, lawyers for a group of federal class action plaintiffs who are suing Trump and his company for allegedly promoting a pyramid scheme wrote to judges in both their case and a civil fraud lawsuit against Trump brought by the New York attorney general. The lawyers suggested that Trump had purposely proposed a trial date in the attorney general’s case that would conflict with the trial date that had already been set in the class action case.

A judge set the trial in the attorney general’s case for this October, and the trial date in the class action case remained scheduled for January 2024.

Trump’s legal thicket has also created an unusual situation in which some people in his orbit have different roles in different cases. Lawyer Evan Corcoran is representing Trump in certain matters and was with him in the courtroom Thursday for his arraignment in the election-interference case. But Corcoran is also a potential witness in the classified documents case. He testified before the grand jury in that case, and the indictment there appears to rely on notes he took in which he recorded Trump’s suggestion that he withhold classified documents from investigators.

It is uncommon for any defendant — not to mention a presidential candidate — to face four concurrent indictments in four different jurisdictions, as Trump may encounter if he is charged in the Georgia investigation, where a grand jury this month is expected to consider charging Trump and allies for efforts to subvert the 2020 election in that state.

Onetime Trump antagonist Michael Avenatti faced three concurrent federal indictments in two jurisdictions, and then a judge in his California case severed that trial into two, meaning Avenatti faced four sets of charges. Avenatti was convicted in two trials in New York and pleaded guilty to some counts in California. The Justice Department then dropped the remaining counts against him.

Aganga-Williams, the former federal prosecutor, said Trump “has the most peril when the cases are overlapping in criminal conduct,” such as with the Georgia probe and the federal election-interference case.

“I think that’s where you would see prosecutors most attuned to what’s happening in other jurisdictions,” Aganga-Williams said.

Trump’s situation also poses particular challenges for his lawyers, who have an outspoken client who is a candidate for federal office. When a client is facing multiple legal challenges, “you have to be conscious of what the client might say that could rebound to the client’s detriment down the road,” said Jonathan Entin, a law professor at Case Western Reserve University.

In Trump’s case, as he tries to fend off a series of legal threats while running for president, “the challenge for a lawyer is to see whether the candidate will not say things on the stump that either jeopardize his legal position or that might rub the judge the wrong way when the judge has to make some sort of discretionary rulings,” Entin said.

“This is really a complicated situation for the lawyer because the lawyer can’t just say, ‘Be quiet for the next six months to a year.’”