Former President Donald Trump walks offstage after his remarks at the Conservative Political Action Conference (CPAC) on February 24, 2024, in National Harbor, Maryland.
CNN  — 

In yet another courtroom, in yet another city, Donald Trump on Friday will star in a fresh episode of a deepening drama over whether he will be tried for federal crimes before November’s general election.

A Florida judge could set a new date for the ex-president’s trial over alleged mishandling of classified documents – a step that could impact other criminal proceedings on Trump’s crowded personal docket.

Special counsel Jack Smith wants Judge Aileen Cannon, a Trump appointee, to schedule a trial, which is sure to be delayed from its current late May start, for July 8. He wants to get at least one court date set in stone, but his choice would heighten the political stakes by setting up a collision with the Republican National Convention a week later, where the former president is expected to claim his third straight GOP nomination.

Friday is another one of those days when Trump is at the center of critical court action in two places at once. More than 550 miles to the northwest in Atlanta, another judge will hear closing arguments in a bid to disqualify Fulton County District Attorney Fani Willis from Trump’s Georgia election interference case. Her ejection could have huge ramifications for the timing and shape of the racketeering trial.

This double slice of courtroom intrigue follows Wednesday’s announcement by the US Supreme Court that it would hear Trump’s claim to sweeping presidential immunity. The decision is likely to push the now-delayed start of his federal election subversion trial closer to, or even past, the 2024 edition.

The constant setting and scrubbing of court dates exemplifies the extraordinary crush of legal trials that are entwined with Trump’s political campaign and that will make this election year as contentious as any in history. In every case, and to every charge, Trump has entered not guilty pleas.

Something as simple as a calendar – more than the fabled rituals of election season like primaries, party conventions and presidential debates – could be a decisive factor in a year when some polls suggest voters’ choices in a close election could be swayed by whether the former president is a convicted felon by Election Day.

Trump, a lifelong serial litigant, is seeking to delay cases – including by testing the appeals process to its limits, even before trial. Because Trump’s legal and political fate are so intertwined, the timing of each of his trials is key. Assuming Trump wins the GOP nod, a conviction before the election could be disastrous for him in a close contest with President Joe Biden. Exit polls in some early Republican primary states have suggested some voters would look at him differently if he were convicted by a jury. But an acquittal of Trump – perhaps in the classified documents case in a potentially friendly jury pool in Florida – could give him an October Surprise-style late campaign boost. And if several of his most contentious trials are postponed until after the election, his central campaign theme that he’s a victim of political persecution could prove less salient. An electoral victory in November, meanwhile, could restore presidential powers to Trump that would enable him to thwart federal trials or even overturn any federal convictions.

Given the jam of cases and potential scheduling conflicts, the chances also appear to be rising that Trump’s legendary flair for avoiding accountability could shield him again, at least temporarily, in the most potentially damaging trials. If that’s the case, the ultimate judgment on Trump in 2024 may be rendered not by juries but by voters.

This week, Trump has had some short-term wins to celebrate, but he also absorbed some legal blows that point to the depth of his vulnerability – especially if he loses the election and faces a grim roster of trials and potential penalties that he will lack the presidential power to mitigate.

• Trump got undeniably good news from the Supreme Court in the immunity case – at least for now.

• He is still waiting to hear if the nation’s top bench strikes down a bid by Colorado’s Supreme Court to bar him from its 2024 ballot under the Constitution’s “insurrectionist ban.”

• In Georgia, even if claims that Willis benefited financially from a relationship with a fellow prosecutor – and that that relationship began before he was hired – may not result in Willis’ disqualification from the case, the hearings may have tainted her image in a way that could help Trump cast doubt on the credibility of the prosecution and any adverse jury verdict.

• But the extraordinary discomfort of Trump’s legal plight is also on display. He is frantically trying to come up with the $454 million he must post in bond prior to an appeal against the verdict in his New York civil fraud trial.

• Also in New York, prosecutors are preparing for Trump’s trial later in March related to a hush money payment to an adult film star. They want a judge to issue a gag order to prevent him from disparaging witnesses and court officials. Trump is sure to argue his political freedoms are being infringed, bolstering his narrative that he’s a victim of persecution by the Biden administration, which had nothing to do with this case, or is a political “dissident,” as he put it at a major conservative conference last week.

Intrigue deepens over classified documents trial in Florida

Trump is expected to attend a hearing on the classified documents case in Fort Pierce, Florida, on Friday.

Cannon has been criticized by some outside experts for a sluggish approach to scheduling and resolving issues over classified material, including some delays that contributed to the need to move past the previously set May trial date. In his proposal for a July 8 start, Smith made a fresh attempt to get one of his trials on the schedule for the summer – before the peak of election season. Now, Cannon must decide whether the parties have sufficient time to prepare and whether other pre-trial motions and work will be complete.

Trump’s lawyers argue that Trump shouldn’t go on trial at all this year because of the election.

“As the leading candidate in the 2024 election, President Trump strongly asserts that a fair trial cannot be conducted this year in a manner consistent with the Constitution, which affords President Trump a Sixth Amendment right to be present and to participate in these proceedings as well as, inter alia, a First Amendment right that he shares with the American people to engage in campaign speech,” Trump’s attorneys said in a filing Thursday.

If Cannon will not delay the trial until after the election, Trump’s lawyers requested an August 12 start date.

The ex-president has pleaded not guilty to dozens of charges related to mishandling of classified documents at his Mar-a-Lago resort after he left the presidency. As in other cases, his legal team has filed multiple attempts to get the case dismissed, which if they do not achieve their objective, may delay proceedings to such an extent that he cannot go on trial before the election. They also argue that Trump is protected by presidential immunity in the case, mirroring arguments his team made in the federal election matter and that the Supreme Court has now decided to hear in April. The latest developments raise the possibility that Cannon might want to hear the outcome of the Supreme Court’s case on the issue, potentially delaying her trial even longer.

Court watchers are keen to learn whether Cannon will set a firm trial date in the hearing and if she does, how much deeper into the calendar she will go as the election looms. If she were to schedule a trial for August, for instance, she could fill subsequent weeks that Smith might hope to use for the federal interference case in Washington, pending the Supreme Court decision on Trump’s immunity claims.

Ryan Goodman, a former special counsel at the Department of Defense, told CNN’s Erin Burnett on Thursday that if Smith is able to secure a July trial date in Florida, he could expect a verdict in August or September. “July 8 and whether or not Judge Cannon goes with the Justice Department is key to that outcome,” Goodman said.

Reverberations from Supreme Court order

The Supreme Court’s decision to hear Trump’s immunity appeal vindicates his delaying strategy. Even if the high court rules by late June, it’s unlikely a federal election interference case could start until late summer at the earliest. Judge Tanya Chutkan would face a decision on whether to press ahead in the final stages of an election when Trump would expect to spend every day on the campaign trial.

Delaying the case until after November could spare the ex-president the possibility of being convicted before he faces the voters — a historic potential stain. But if the trial is a go for the fall, voters would get a refresher course in Trump’s attempts to destroy democracy after the 2020 election and his actions leading up to the mob assault on the US Capitol on January 6, 2021. While the trial is not expected to be televised, it would be a media spectacle nonetheless and would dominate the endgame of the campaign at a time when voters are casting early ballots and finalizing their choices.

Trump’s lawyers would be certain to raise the question of whether he could obtain a fair trial from a jury at a time when Americans will be bombarded with political news. The Justice Department typically seeks to avoid initiating politically sensitive cases around 90 days before an election. Yet officials could argue that Trump, with his multiple delaying tactics, had closed off his own options for a speedier trial.

Elliot Williams, a former federal prosecutor, categorically rejected the idea that a close encounter between a federal election trial and the 2024 election would deprive Trump of fair treatment.

“He can get a fair trial. And I want to pour cold – ice-cold – water on the notion that he can’t,” Williams said on “CNN This Morning” Thursday.

“Now, the idea is, can he get a trial by August, September? That would be lightning-fast – if the moment they walked out of the Supreme Court in June, everybody ran to the courthouse and started preparing for trial. To get everything started by August or September would really be record-breaking, I think.”