How Trump’s lawyers and campaign staff are handling the chaotic collision of his trial and political operations

By | November 6, 2023


Between campaign stops and courtroom appearancesFormer President Donald Trump is quietly preparing to take the witness stand in his civil trial for fraud in New York, meeting with his lawyers before his testimony Monday, sources familiar with the preparations told CNN.

This is the first time Trump himself will be subjected to extensive courtroom questioning during his term. A legally burdensome post-presidency, something he should try to capitalize on politically. He has already turned his legal threat into a successful campaign slogan, arguing to his base that he is the victim of a politicized justice system.

“Lawsuits are becoming an increasingly important part of campaign strategy,” a Trump campaign adviser told CNN. “It all comes together 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 expected to hold a rally in South Florida in an effort to steal the spotlight from his 2024 Republican opponents, who will be right next door to face off in the third GOP presidential debate.

As Trump begins his third White House campaign, his legal and political operations are beginning to collide, leading to scheduling problems and uncertainty for both his lawyers and campaign staff. Things will only get more complicated over the next year, as the 2024 election gets into full swing, just as a number of Trump’s trials are getting 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, attending the testimony of his former lawyer Michael Cohen while preparing his own testimony. Then he was in Florida for back-to-back campaign and PAC fundraisers. After a weekend of campaigning just outside Orlando, Trump was back in New York on Sunday to prepare for trial with his lawyers.

The line between Trump’s political campaign and his legal action is becoming increasingly blurred. Campaign emails alternate between attacks on Florida Governor Ron DeSantis, his main GOP rival, and the reaction to recent legal developments. And his fundraising appeals cover everything from highlights of his rallies to critiques of the prosecutors leading the case against him.

Meanwhile, Trump’s advisers have been developing tentative plans for how to balance his upcoming trial dates with a robust campaign effort, several sources familiar with the conversations told CNN. But these projects depend on trial schedules that are beyond their control, forcing the Trump campaign team to respond to possible summons within very short deadlines.

“It’s not like we have a choice — we schedule trial dates, knowing they might get moved,” another Trump campaign adviser told CNN. “This requires us to not plan as far in advance as we normally would, because you want to cancel or reschedule as little as possible.”

So far, Trump’s presence at his fraud trial in New York has left his campaign scrambling to respond to him. Many of the former president’s decisions to appear in court were made at the last minute, sources familiar with the planning process told CNN.

Mike Segar/Pool/Reuters

Former President Donald Trump attends the Trump Organization fraud civil trial in New York State Supreme Court on October 24.

Trump spent the last day of September campaigning in Iowa before flying straight to New York on the eve of the first day of his civil fraud trial. His team spent the days leading up to his court appearance thinking about how to organize the schedule change. In the following weeks, as Trump increasingly wanted to attend the trial, his team had to make similar arrangements.

These impromptu decisions are further complicated by Trump’s strong security presence. While Trump flies in his private plane, the Secret Service is by his side at all times and increased law enforcement is on the ground wherever he travels.

The logistics will become more complicated next year, as the presidential primary schedule becomes intertwined with a number of Trump’s trials.

On January 15, the same day as the Iowa caucuses, Trump began his civil defamation lawsuit filed by E. Jean Carroll, a former magazine columnist who won the jury verdict this year against him over allegations he sexually assaulted her 27 years ago.

On March 4, the Trump federal government election interference lawsuit begins in Washington, DC. The next day is Super Tuesday, when Texas, California and a dozen other states hold their primaries in the biggest delegate prize of the year.

Later that month, on March 25, Trump’s speech criminal trial in New York linked to secret payments made in 2016 should begin. And on May 20, the criminal trial in the special prosecutor’s case regarding the former president’s possession of classified documents should start.

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

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

Jabin Botsford/The Washington Post/Getty Images

Former President Donald Trump speaks at a campaign rally Oct. 23 in Derry, New Hampshire.

The vast projects will be the result of a collaboration between his campaign and the legal teams, who will try to develop a strategy capable of carrying them out until next November.

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

Although these extenuating circumstances would likely kill most political campaigns, advisers insist that Trump has the resources to handle them.

“You have a guy who has the assets to pull this off,” a Trump aide told CNN. “Turn on the plane and make it happen.”

But not all advisors see the situation with such rosy glasses.

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

Trump is surrounded by what is widely considered his most disciplined political campaign team yet. Led by veteran Republicans Susie Wiles and Chris LaCivita, the campaign focused on building infrastructure in early-voting states, using years of data collected from Trump rallies to target potential voters and reintroduce Trump into retail politics.

Trump’s legal peril is a necessary issue that must be addressed in the eyes of many of his advisers.

Bob Self/Florida Times-Union/USA Today Network

Trump campaign advisor Susie Wiles is seen in 2015.

“We don’t think this will 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 on-the-ground action and work in early-voting states will likely remain effective, even if Trump cannot consistently campaign on the ground.

“Let’s say he’s in court for 10 days between now and (the Iowa caucuses) on January 15th. Will this fundamentally alter Donald Trump’s victory trajectory in Iowa? No,” the source close to Trump said. “And in fact, (it) might help it because of the sheer volume of media coverage and the discipline applied to the messaging that this is election interference.” »

Although there was initial concern that Trump’s increased poll numbers and donations would only be felt in the short term, and only among primary voters, the steady influx of money following multiple arrests and indictments has gave some members of Trump’s team and his close allies a renewed sense of confidence. – some believe his legal battles could even help him in a general election.

“If these things were really going to hurt him in general, it would be reflected in the polls right now. We were sort 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 the fact that it could turn off a large portion of voters in the general election.

“We’ll cross that bridge when we come to it,” Trump’s second campaign adviser said.

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