Former President Donald Trump’s lawyers see a major opportunity this week to use his criminal document mishandling case in Florida to create an impasse on his calendar for the two federal judges overseeing his major criminal cases.

Juggling his campaign and court calendar and playing his cases off one another is a key part of Trump’s legal strategy. The ultimate goal, his team has said openly, is to prevent Trump from being tried in federal court before voters cast their ballots in the 2024 general election.

A primary aim for Trump’s legal team, according to people familiar with the strategy, is to put the judge in DC overseeing the 2020 federal election obstruction case, Tanya Chutkan, in a position where she can’t start a trial before Election Day.

“Meaning, ice her,” said a person familiar with Trump’s trial schedule strategy. “Making it impossible for her to jam a trial down before the election, by things that are out of her control.”

Chutkan set an initial trial date for March 4, which has been delayed indefinitely because of appeals. Yet if the Supreme Court returns the case to Chutkan, that trial could be back on the calendar within a month or two.

One way to hamper Chutkan is to convince the judge in Florida, Aileen Cannon, to move Trump’s Mar-a-Lago document mishandling trial from late May until the summer.

Then, as summer approaches, the Mar-a-Lago case may require Cannon to push the trial back again and again because of the legal complexities around classified documents that still have to be worked out, according to people familiar with the case.

Trump has already asked the federal judges and a state judge in a third criminal case he faces, the Georgia election subversion case, to delay any trials until after the November election. Both federal judges, Chutkan and Cannon, have said no. But a gradually shifting calendar could be just as effective at shielding Trump from other trials through the summer, multiple sources familiar with the former president’s legal strategy told CNN.

Cannon has signaled a willingness in recent months to considering pushing back the date. And the prosecutors and defense teams are engaged in protracted court fights over access to evidence – classified records and information from far corners of the federal government – that Cannon still has to resolve. Cannon is a Trump appointee in an area of Florida with many Trump voters in a potential jury pool. She drew bipartisan criticism in the legal world for how she handled an earlier part of the case and has moved slowly to resolve the pretrial issues.

Chutkan’s court is an entirely different profile – where the Washington, DC, jury pool leans liberal and has convicted many January 6, 2021, rioters at trials. Chutkan is a Barack Obama appointee who ruled against Trump on the key issue of the case – presidential immunity – and also issued a limited gag order against the former president.

Chutkan “might have him on trial the day of the election. If she wants to do that, we might as well just make Trump president right now,” one of the sources said.

Trump often uses his court proceedings to draw attention to his prosecutions, calling them politically motivated. While he frequently makes campaign speeches outside courtrooms, Trump isn’t required to attend most pretrial hearings, and he isn’t even required to be in the courtroom as a defendant after a trial begins.

“The Special Counsel seeks urgently to force President Trump into a months-long criminal trial at the height of campaign season, effectively sidelining him and preventing him from campaigning against the current President,” Trump’s lawyers recently wrote to the Supreme Court, which has his 2020 election case on hold as it looks at questions he raised around presidential immunity.

Critical hearing in Florida on Friday

While the two federal cases remain in limbo, Trump will first go on trial in late March in Manhattan, in a fourth criminal case in which he is accused of falsifying business records to cover up hush money payments to adult film star Stormy Daniels to protect his 2016 presidential campaign. That trial could last into May, according to the judge on the case.

That case is seen by Trump’s advisers as one that will try him on less serious charges than in his other three criminal indictments and raises less substantial issues about his fitness for office as he runs for president again. Americans who have responded to a Quinnipiac University poll last fall agreed the New York charges were less serious than his other charges.

“That’s the one that has the least consequence. He doesn’t face jail time even if convicted,” one person familiar with Trump’s legal approach told CNN.

The Florida documents case is scheduled to follow the New York trial, with a start date set for the end of May.

Trump, his team, his co-defendants and the special counsel’s office prosecutors are set to appear before Cannon in her Fort Pierce, Florida, courthouse Friday.

“We most certainly are going to ask to move that trial date,” Trump defense lawyer Todd Blanche said about the documents case schedule at a separate hearing in the New York case earlier this month.

Friday’s hearing is expected to grapple with scheduling issues but could last hours and delve into meatier tensions in the case. It is not expected to address all the legal questions Trump has mounted, such as his attempts to get access to more evidence or his arguments to dismiss his case.

The former president’s bid to claim presidential immunity in the Mar-a-Lago case – saying he was able to remove national security documents from the White House just before he left office because he deemed them “personal” records while he was still president – would likely be discussed later and could prompt another rare appeal before a trial.

Already, Trump’s team is considering asking Cannon to reschedule the trial in Florida for a month or two later, so that it would be reset for July, according to sources familiar with his strategy.

That would create a hole in Trump’s court schedule after the New York trial that no other case is positioned to fill. It would also block out his calendar for a crucial window from July into September.

Trump’s team believes the Mar-a-Lago case, if it’s moved July, could box out Chutkan from putting the federal election subversion case on the schedule once Supreme Court appeals are addressed. When July nears, Trump’s team or the special counsel’s office could ask Cannon again to move the Mar-a-Lago trial back, and she may consider it because of the complexities in the case.

Chutkan has made clear she believes Trump should be tried in her courtroom on a tight schedule.

The special counsel’s office has repeatedly argued that the public, too, deserves to have Trump’s federal election case before a jury quickly, potentially even before the next presidential election.

“[Trump’s] personal interest in postponing trial proceedings must be weighed against two powerful countervailing considerations: the government’s interest in fully presenting its case without undue delay; and the public’s compelling interest in a prompt disposition of the case,” the Justice Department wrote to the Supreme Court recently.

“The charges here involve applicant’s alleged efforts to disenfranchise tens of millions of voters,” the special counsel’s office added. “The national interest in resolving those charges without further delay is compelling.”

Of course, Chutkan could still set a court date that overlaps with other judges’ cases if the 2020 election case returns to her courtroom from the Supreme Court. While Trump couldn’t be on trial simultaneously in two different courts, judges could have overlapping schedules initially because trial dates can often move.

Judges may confer on timing

New York state Supreme Court Judge Juan Merchan, who is overseeing Trump’s hush money criminal case, disclosed publicly he had been in touch with Chutkan as recently as this month. The two judges had initially both scheduled trials for March.

“There is a lot of moving parts in the DC case. Really nobody knows what’s going to happen and when it’s going to happen,” Merchan said at a recent hearing, announcing his court would hold jury selection for Trump on March 25.

Blanche, who represents Trump in multiple criminal cases, called the quick trial a “grave injustice” and “election interference.”

“We have been faced with extremely compressed and expedited schedules in each and every one of those trials,” Blanche told Merchan at the hearing. He added that the legal team was swamped with work, and Trump, involved in his cases, was busy too.

Merchan previously called out Trump’s team for trying to play his New York trial date against his 2020 election case before Chutkan, so neither would move forward.

“We would have wound up adjourning our case only to see the DC case not start on March 4,” Merchan said. “That’s the problem with jock[ey]ing and moving when there are multiple parts, and we don’t all have control over each one of those parts.”

Merchan acknowledged Trump shouldn’t be on trial in more than one court at once.

“Mr. Trump does have an absolute right to be present in all of his criminal trials,” the judge said at the hearing. “It’s an important right, and one that he has every right to certainly take advantage of. He’s not going to be in more than one criminal trial at the same time.”

CNN’s Hannah Rabinowitz and Holmes Lybrand contributed to this report.