As Trump’s legal and political schedules collide, his lawyers and campaign staff manage the chaos

Between campaign stops and courtroom appearances, former President Donald Trump has been quietly preparing to take the witness stand in his civil fraud trial in New York, meeting with his lawyers ahead of his testimony Monday, sources familiar with the preparations tell CNN.

It marks the first time Trump himself will be subject to extensive courtroom questioning during his legally fraught post-presidency, something he is expected to try to capitalize on politically. He’s already turned his legal jeopardy into a successful campaign slogan, arguing to his base that he is the victim of a politicized justice system.

“The legal cases have increasingly become a big part of the campaign strategy,” a Trump campaign adviser told CNN. “It all bleeds into one and it’s obviously a big winner.”

Trump’s team expects his appearance to last just one day. But his testimony could complicate his campaign schedule if it extends into Wednesday. That night Trump is slated to hold a rally in South Florida in an effort to steal the spotlight from his 2024 Republican challengers, who will be just down the road sparring at the third GOP presidential debate.

As Trump makes his third run for the White House, his legal and political operations are beginning to collide, leading to scheduling headaches and uncertainty for both his lawyers and campaign staffers. Things will only get more complicated over the next year, as the 2024 election swings into full gear just as a number of Trump’s trials get underway.

Trump’s schedule already has him bouncing between the campaign trail and courtrooms. On a recent Monday, he was in New Hampshire for a rally. The next day, he was in New York, sitting in on the testimony of his former lawyer Michael Cohen while also prepping for his own testimony. Then he was in Florida for back-to-back campaign and PAC fundraisers. After a weekend campaign event just outside Orlando, Trump was back in New York on Sunday for trial prep with his lawyers.

The line between Trump’s political campaign and his legal operation gets blurrier by the day. Campaign email blasts alternate between attacks on Florida Gov. Ron DeSantis, his GOP primary rival, and reaction to recent court developments. And his fundraising appeals cover everything from highlights from his rallies to slamming the prosecutors leading the cases against him.

Meanwhile, Trump’s advisers have been making tentative plans for how to balance his upcoming trial dates with a robust campaign effort, multiple sources familiar with the conversations tell CNN. But those plans are reliant on trial schedules that are out of their hands, forcing Trump’s campaign team to respond to potential summons with little lead time.

“It’s not like we have any choice – we are planning around what we believe the trial dates will be, knowing that they could move,” another Trump campaign adviser told CNN. “It requires us to not plan as far in advance as we would normally because you want to cancel or reschedule as little as possible.”

‘There is nothing manageable about this’

Trump’s attendance at his fraud trial in New York City thus far has forced his campaign at times to scramble to accommodate him. Many of the former president’s decisions to show up in court have happened at the eleventh hour, sources familiar with the planning process told CNN.

Former President Donald Trump attends the Trump Organization civil fraud trial in New York State Supreme Court on October 24. - Mike Segar/Pool/Reuters
Former President Donald Trump attends the Trump Organization civil fraud trial in New York State Supreme Court on October 24. - Mike Segar/Pool/Reuters

Trump spent the last day of September campaigning in Iowa before flying directly to New York City on the eve of the first day of his civil fraud trial. His team spent the days leading up to his appearance in court plotting how to arrange for the shift in his schedule. Over the following few weeks, as Trump increasingly became interested in attending the trial, his team had to make similar arrangements.

Those spur-of-the-moment decisions are further complicated by Trump’s extensive security presence. While Trump flies in his private plane, Secret Service is with him at all times and heightened law enforcement is on the ground to and from wherever he travels.

The logistics will get more complicated next year as the presidential primary calendar intertwines with a number of Trump’s trials.

On January 15, the same day as the Iowa caucuses, Trump begins his civil defamation trial brought by E. Jean Carroll, a former magazine columnist who won a jury verdict this year against him over claims that he sexually abused her 27 years ago.

On March 4, Trump’s federal election interference trial begins in Washington, DC. The following day is Super Tuesday, when Texas, California and a dozen other states hold their primaries in the largest delegate prize of the year.

Later that month, on March 25, Trump’s criminal trial in New York related to hush-money payments made in 2016 is set begin. And on May 20, the criminal trial in the special counsel’s case regarding the former president’s possession of classified documents is slated to start.

The former president’s advisers are still hopeful that Trump’s legal team will file successful motions that will delay the trials beyond some of the critical dates on the political calendar.

“There are still lots of legal maneuverings that will take place in a lot of these cases that delay these trials,” a source close to Trump said. “However, we plan for every contingency – every single one, whether they’re viable or not.”

Former President Donald Trump speaks at a campaign rally on October 23, in Derry, New Hampshire. - Jabin Botsford/The Washington Post/Getty Images
Former President Donald Trump speaks at a campaign rally on October 23, in Derry, New Hampshire. - Jabin Botsford/The Washington Post/Getty Images

The extensive plans will be a collaboration between his campaign and legal teams, as they attempt to build a strategy that can carry them through next November.

“The planning starts with the lawyers – they provide trial dates and an estimate of how long (Trump) needs to be there and what days he has to be there,” the second campaign adviser added.

While these extenuating circumstances would likely kill most political campaigns, advisers insist that Trump has the resources to manage.

“You’ve got a guy who has the assets to pull this off,” a Trump aide told CNN. “Fire up the plane and make it happen.”

But not all advisers view the predicament through such rosy glasses.

“There is nothing manageable about this,” the second campaign adviser told CNN.

‘Cross that bridge when we get there’

Trump is surrounded by what is widely viewed as his most disciplined political campaign team to date. Led by seasoned Republicans Susie Wiles and Chris LaCivita, the campaign has focused on building an infrastructure in early voting states, using years of data gathered from Trump rallies to target potential voters and reintroducing Trump to retail politics.

Trump’s legal peril is a necessary issue that has to be dealt with in the eyes of many of his advisers.

Trump campaign adviser Susie Wiles is seen in 2015. - Bob Self/Florida Times-Union/USA Today Network
Trump campaign adviser Susie Wiles is seen in 2015. - Bob Self/Florida Times-Union/USA Today Network

“We don’t think it’s going to impact our ability to win, but we certainly know and recognize that it adds an additional level of complexity,” the source close to Trump said.

The source added that their ground game and work in early-voting states is likely to stay effective, even if Trump cannot constantly be on the ground campaigning.

“Let’s say he is in court for 10 days between now and (the Iowa caucuses on) January 15. Is that going to fundamentally alter Donald Trump’s trajectory to win in Iowa? Nope,” the source close to Trump said. “And in fact, (it) could help him because of the sheer volume of coverage and the discipline on the messaging that this is election interference.”

While there was preliminary concern that Trump’s boost in polling and donations would only be felt in the short term, and only among primary voters, the consistent cash influx over multiple arrests and indictments has given some of Trump’s team and close allies a renewed sense of confidence – with some believing that his legal battles may even help him in a general election.

“If this stuff was gonna really hurt him in general, that would be reflected in the polling right now. We were kind of forced into it. It’s not like we chose this. But what’s happening legally has become a political strategy,” a Trump ally told CNN.

But advisers also acknowledged the unprecedented nature of the former president’s situation, and that it could turn off a large swath of general election voters.

“We’ll cross that bridge when we get there,” the second Trump campaign adviser said.

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