“Announcing before the midterms allows him to clear the field, shore up the donor base and take a victory lap after the midterms,” one former Trump campaign official said.
But the prospect of Trump launching a third bid for the White House as an end-of-summer or October surprise has worried many of these allies, who think the timing is premature. More than 10 Trump confidants, advisers and aides who spoke on the condition of anonymity said they have personally advised the 45th President to hold off on a formal campaign launch until next year. They noted the careful planning it would take to pull off an announcement that commands deference from other Republican hopefuls and injects excitement into corners of the GOP that crave a new standard-bearer and have quietly debated whether someone like DeSantis, whom Republicans widely consider a new-dand-improved version of Trump, might be more competitive in a general election.
“I don’t think the lack of planning means he’s not actually serious about running. It just means it’s going to be another fly-by-the-seat-of-his-pants sh– show if he does,” said one person close to Trump.
Trump has, of course, taken some steps that are customary for would-be candidates. He has stuck his neck out with high-profile endorsements in key Senate and gubernatorial contests, winning some and losing others. He has built a thriving post-presidential fundraising operation with around $110 million currently in its war chest — topping what both national parties have in the bank. And he has worked to maintain a close relationship with key supporters through periodic campaign rallies and appearances at conservative events. Later this week, he will deliver remarks at the Faith & Freedom Coalition’s annual conference for religious conservatives in Nashville, Tennessee — joining other possible 2024 GOP hopefuls on the speaking roster.
Still, those around Trump who say he is keen on announcing a campaign this year admit that his overall infrastructure is still lacking. One longtime Trump pal also said the former President needs to spend more time beta-testing different messages before throwing his hat in the ring because his false claim that the 2020 election was stolen “is not enough on its own to justify running again.”
“A red wave in November would give him the perfect opportunity to adopt a forward-looking message. He can talk about what Republicans will do to turn the country around now that they have more control and what he would do in a second term to boost those efforts,” this person said.
Questions about staffing
A key question for allies of the former President is who, exactly, would be involved in his campaign if he announces before the November midterms. That timing would come on the heels of public hearings by the House select committee investigating the January 6, 2021, attack on the US Capitol that have featured damning testimony from both Trump’s family members and former aides and advisers.
While Trump has yet to abandon his practice of consulting a rotating cast of friends, family members and advisers about his political decisions, it is unclear who among his kitchen cabinet would actually commit themselves to another presidential campaign. He has complained, both privately and publicly, about former aides such as Mark Meadows and Kellyanne Conway, who have detailed their experiences in the Trump White House with personal memoirs, and has an increasingly limited number of advisers who are neither profiting off their proximity to him or directly on his payroll — limiting his willingness to trust their intentions.
“He won’t have trouble attracting people if he runs, the trouble will be in who he attracts,” said the former Trump campaign official, who wasn’t ready to commit to working on his 2024 campaign if he runs. “If it resembles anything like 2016 or 2020, there were days when we spent 18 or 19 hours at Trump Tower because of how short-staffed he was. That scares me off a little bit.”
Meanwhile, other former members of Trump’s inner circle have voluntarily created distance.
Trump’s daughter Ivanka Trump and son-in-law Jared Kushner are no longer part of his everyday political operation, said multiple people familiar with the situation, noting that the couple has spent most of the past 18 months focused on their children, settling into the Miami area, and ensuring the success of Kushner’s new investment fund, Affinity Partners.
“I don’t see them being all that involved strategically,” said a second person close to Trump. “Trump trusts [Ivanka] but she’s not knee deep in this like most of his advisers.”
In fact, in a post to his Truth Social website following the January 6 committee’s first public hearing last week, Trump rebuffed his daughter’s sworn testimony that she believed there was insufficient evidence of fraud in the 2020 election — claiming “she had long since checked out” during the final months of his presidency.
In the couple’s absence, the former President has been turning more frequently to his son, Donald Trump Jr., for advice on candidate endorsements and messaging.
“Obviously, if he does make an announcement, the Democrat machine will be fully against him, and they will spend so much money trying to knock him out. Once he announces, the negativity will be ramped up, so that’s why it’s important to figure out in advance who is going to be responding to that stuff besides the candidate himself,” the former Trump campaign official said.
But one current Trump adviser disputed the idea that the former President could be in a precarious position if he launches another presidential campaign later this summer or in the early fall. This adviser pointed to recent campaign finance reports from Trump’s various fundraising committees showing the thousands of dollars he has been spending each month on payroll during his post-presidency.
“In terms of a campaign manager,” the adviser added, “he really doesn’t need one right now.”
“I think  will be decent. Both 2016 and 2020 started very different but got to a place that was really well organized and highly functioning as a campaign operation. He has done this twice now and can put together a pretty good infrastructure” when he wants, the adviser said.
Two people familiar with the matter said Trump has rented out some off-site office space in Palm Beach, Florida, for those involved in his Save America PAC. And the expectation across his orbit is that any 2024 campaign will be headquartered in Florida, most likely at his current residence.
“Mar-a-Lago will be the campaign HQ and he’ll rent space onsite to the campaign for an exorbitant rate,” said one of the people close to Trump in a nod to the former President’s practice of blurring the lines between his business ventures and political activities.
‘The ball will start rolling’
For his part, Trump sees his travels for the 2022 midterms and existing fundraising machine as preparation enough for a third presidential run — two steps that leave him ready to announce at a moment’s notice.
But once the former President settles on an actual announcement date, allies expect he will want to go all in to attract the media attention and shock value his recent campaign rallies have been lacking. That, of course, will take time to plan out.
“There hasn’t been a pick-up-the-phone, ‘We’re doing this by X date,’ conversation yet. Once that happens, the ball will start rolling,” said a third person close to Trump. “What I expect to happen is we will get to mid-summer, and he’ll let a very small group of people know he’s ready and to start organizing without causing too much noise.”
In the meantime, Trump has been tending to his relationships with top House Republicans — hoping to have an army of MAGA surrogates ready to support him from Capitol Hill if he runs — and working to remain relevant with appearances in 2022 battlegrounds and venues that guarantee him adoring crowds. He will do that Friday when he addresses the audience in Nashville, an appearance he will use to respond to this week’s public hearings by the congressional panel investigating January 6.
There is one additional consideration Trump has privately discussed with aides and allies as he weighs the timing of a 2024 announcement. The former President remains under investigation in Georgia, where Fulton County District Attorney Fani Willis has impaneled a special grand jury to determine whether Trump’s efforts to overturn the 2020 election results in Georgia warrant criminal prosecution. When the grand jury finishes its work, which could take several months, it will issue a report detailing its findings. Two people close to Trump said he is closely monitoring that probe but isn’t treating it as a primary factor in his 2024 decision.
“That is a storyline that could dominate the fall and first quarter of a presidential cycle, so there is a calculation of getting out in front of it,” said one of the people close to Trump.