'Not an easy transition': Inside Trump's unconventional first months out of office

Feb. 28: Trump teases 2024 presidential run Donald Trump spoke at the Conservative Political Action Conference on Feb. 28, marking his first public appearance in over a month.

Most Mondays and Tuesdays, former U.S. president Donald Trump skips golf to confer with aides about the week ahead.

Together they decide which Republican candidates he will meet with at his office -- a converted bridal suite above Mar-a-Lago's 20,000-square-foot ballroom -- and whether they deserve his support. Often, he'll ask for updates on his leadership PAC and political operation, or spend hours chatting by phone with a coterie of old friends.

Far from a conventional post-White House retirement, Trump's first 100 days out of office illustrate a man who has preferred plotting the next chapter of his political career to planning his presidential library, recruiting MAGA-aligned Republican primary challengers to writing a post-presidential memoir. Whereas his predecessors disengaged from politics for months after leaving office, Trump has turned the same political warfare that defined his presidency into a full-time retirement hobby as he weighs a full return to the spotlight with a potential comeback presidential bid in 2024.

"He didn't play by the rules as president and he's certainly not going to as an ex-president," Newsmax CEO and longtime Trump pal Chris Ruddy said.

More than a dozen Trump aides, confidants and allies who spoke with CNN -- many of whom were granted anonymity to candidly discuss his post-presidency -- say the former president, who remains bitter about his defeat in the 2020 election, has nevertheless come to enjoy his status as a GOP kingmaker, relishing his ability to disrupt races or elevate pro-Trump figures against dissenters inside the party. Others noted that he is yearning to return to the White House and claimed that his efforts to build a post-presidential political machine are principally aimed at supporting that goal.

Most days of the week, Trump begins with 9 a.m. tee times at his namesake golf course 15 minutes from his home. He usually plays 18 holes, but he sometimes stays for the course's full 27, followed by a leisurely lunch at its clubhouse with a rotating cast of friends. These days, friends say, he avoids the buffet.

Trump then conducts candidate interviews or meetings with his staff back at his oceanfront resort until 7:30 p.m. before joining his wife, Melania, for dinner on Mar-a-Lago's bustling terrace. In recent weeks, the couple has dined with former House Speaker Newt Gingrich and his wife, Callista, who served as U.S. ambassador to the Holy See during the Trump administration, and former White House counselor Kellyanne Conway, who remains a close friend.

"Right now, he's doing a very good job sustaining his movement in case he does decide to run," Gingrich said.

'NOT AN EASY TRANSITION'

It took Trump several weeks to get settled into his post-White House life.

Because he had refused to accept his loss to President Joe Biden, who emerged from the November election with a 306-to-232 victory in the Electoral College, few preparations had been made to prime the luxury South Florida resort for his arrival.

For their first few weeks on the job, a small team of aides paid by the General Services Administration to oversee his transition operated out of a villa on resort grounds with no office phones, computers or desks. Formally, Trump was allowed to select the modest team, whose salaries are customarily paid for by the GSA in accordance with the Former Presidents Act.

But almost immediately, an assortment of other advisers were invited by Trump to oversee construction of his new political operation -- one he hoped would guard his rank as de facto leader of the Republican Party and lend support to allies in local, state and federal races who could advance his agenda. Among them were Trump campaign lawyer Justin Clark and attorney Alex Cannon, former Trump campaign managers Bill Stepien and Brad Parscale, senior adviser Jason Miller, former White House social media director Dan Scavino and longtime allies Corey Lewandowski and Dave Bossie.

While the hangers-on from Trump's reelection campaign began to fine-tune his post-White House apparatus -- including Save America, a cash-flush leadership PAC created last year that has allowed him to back candidates for public office, and a separate super PAC led by Lewandowski -- the ex-president resumed outreach to others in his orbit.

People familiar with these interactions said Trump has regularly called Conway, former Florida Attorney General Pam Bondi, former White House chief of staff Mark Meadows, Sens. Lindsey Graham of South Carolina and Rand Paul of Kentucky, and Rep. Jim Jordan of Ohio for messaging and political advice or to complain about Biden and Democratic leaders. And when outside advisers started warning him in March that his post-presidential operation -- particularly his methods for vetting candidate endorsements -- appeared disorganized, Trump hauled in another longtime ally, Florida-based GOP strategist Susie Wiles, to instill order.

A person close to Trump who fielded multiple disgruntled calls from the former president in his first few weeks out of office said it took him several weeks to overcome the isolation he felt after hundreds of his supporters stormed the U.S. Capitol on Jan. 6 and he was thrust into a political exile. After he arrived at Mar-a-Lago following a low-key sendoff at Joint Base Andrews the morning of Biden's inauguration, this person said Trump would talk about forming a third party and complain that Republicans, like House Minority Leader Kevin McCarthy of California, couldn't wait to get rid of him -- noting that his focus was on the past, not the future, which contributed to the early chaos in his post-presidential operation.

"Most people would leave the White House relieved to have the weight of the world lifted off their shoulders, but for him it was a reality that took some time to get used to. Those first few weeks, it was not an easy transition," said the person close to Trump.

BUILDING HIS EMPIRE

By mid-February, Trump -- convinced by aides and Republican party leaders that 2022 should be his immediate focus and still interested in exacting revenge against GOP incumbents who had voted to impeach him or dismissed his election fraud charade -- began discussing candidate endorsements with his team.

The former president already had a laundry list of prospective primary challengers lined up to take on his foes inside the party. But privately, he was working the phones to recruit more.

In Georgia, he encouraged GOP Rep. Jody Hice to launch a bid to unseat Secretary of State Brad Raffensperger, who repeatedly rejected Trump's baseless claims of rampant voter fraud in the state and is currently cooperating with state investigators as they investigate a Jan. 2 phone call in which then-president Trump asked Raffensberger to find the votes needed to flip the state into his column. In Ohio, where Trump has yet to bestow his blessing on one of the several Republican candidates running to fill outgoing GOP Sen. Rob Portman's seat, the former president reportedly grilled four of the contenders at his Palm Beach golf club before a fundraiser last month.

Aides say Trump is still on the hunt for a primary recruit in Georgia's 2022 gubernatorial race due to his dissatisfaction with Republican Gov. Brian Kemp's handling of the 2020 results in his state.

They note he is also vetting challengers to Sen. Lisa Murkowski of Alaska, the only Senate Republican facing reelection next fall who voted to convict him after his second impeachment trial earlier this year. He has plans to target the 10 House Republicans who voted to impeach him and are hoping to hang on to their seats in the upcoming midterm elections, as well.

Occasionally, the 45th president has invited candidates to meet with him at Mar-a-Lago who he has no intention of endorsing. One Trump aide said he enjoys the lavish praise and frequently crows to guests at the club about the weight his support carries. He has similarly hosted incumbent Republicans who have echoed his false claims about the Jan. 6 insurrection and are already widely expected to receive his endorsement.

Last week, for instance, Trump met with Rep. Claudia Tenney, a New York Republican who has falsely asserted that many of the insurrectionists who ransacked the halls of Congress "probably weren't ever Trump people."

Next month, these proverbial pilgrimages to Mar-a-Lago will end as Trump escapes the hot Florida summer to relocate to his golf club in Bedminster, N.J. The move has frustrated some allies who view his Florida resort as an ideal access point to wealthy Republican donors in the area -- including former Commerce Secretary Wilbur Ross, who former Trump aides starting their own political outfits have solicited for financial support -- and who are wary of the old friends Trump will encounter during his stay up North.

"A lot of his aides and allies thought Florida was going to be the center of the Earth for the next two years, and now he's up and out of there," said a former senior administration official. "His Bedminster club is much more closely knit, and you really never know who's going to show up."

People familiar with his plans said Trump will continue to host meetings at Bedminster, where he conducted many of his interviews for Cabinet posts during the 2016 presidential transition and where the conference rooms and office space may create an environment that is more conducive to his post-presidential planning. The New Jersey venue will also serve as the backdrop for lengthy interviews of which Trump is the subject, as he continues meeting with journalists who are penning books about his presidency and already completed first-round interviews at Mar-a-Lago.

"Our expectation is that the fundraisers and meetings will continue undisrupted. He'll probably want to host people in his living room at the cottage in Bedminster," said one person close to Trump's operation.

DECIDING WHAT HIS FUTURE HOLDS

Some Trump allies are hoping this summer will provide clarity about the former president's 2024 ambitions and his plans to assist candidates he's already endorsed, or who he plans to, ahead of the midterm elections in November 2022.

Trump has played coy about his desire to seek a second term -- declining to either rule out a bid or commit to running -- while promoting Republicans who are widely seen as strong contenders themselves for the party's nomination. In a March 22 appearance on "The Truth with Lisa Boothe," Trump said the GOP has "a pretty deep bench" of possible contenders and went so far as to name-check Florida Gov. Ron DeSantis, South Dakota Gov. Kristi Noem and Sen. Josh Hawley of Missouri.

His noncommittal posturing has frustrated some allies, who worry he is blowing an opportunity to take control of the GOP early on and opening the door for other presidential hopefuls to forge relationships with his supporters.

"It's important to have a field-clearing exercise sooner rather than later if he's going to run, otherwise some of these other guys are going to start getting momentum," said the former senior administration official.

Indeed, some rumoured 2024 contenders have been laying the groundwork for their own potential campaigns with appearances in states that will play a critical role in the Republican presidential primary and general election: Former Vice President Mike Pence will deliver his first public address since leaving office in South Carolina this week. Former Secretary of State Mike Pompeo, who visited Iowa in March, also appeared virtually at a fundraiser last month for New Hampshire Republicans. And both DeSantis and former U.S. Ambassador to the United Nations Nikki Haley are due for appearances in Pennsylvania and Iowa, respectively, in the next two months. Sens. Rick Scott of Florida, Tom Cotton of Arkansas and Tim Scott of South Carolina have also made recent stops in Iowa -- or plan to in coming months -- fuelling speculation about their presidential ambitions.

Other Trump allies have urged him to fine-tune his post-presidential messaging, which has featured ruthless attacks against Republican Party leaders and incumbent GOP officeholders and only recently drifted into regular criticism of the Biden administration. They say the vengeance-driven strategy he has deployed so far is unlikely to be helpful in the long term and ignores what they view as layup opportunities to target Biden and Democratic leaders over issues like immigration, taxes and identity politics.

"I think the radicalism of the Democrats is going to rebound enormously to Trump's benefit and he would be better off to focus on the Democrats. He has enough friends to go after disloyal Republicans," said Gingrich.

"He should take the higher position and focus on larger domestic issues and international crises," added Newsmax CEO Ruddy.

While aides say Trump has recently been paying more attention to Biden's agenda and policy decisions -- last week he issued a statement criticizing Biden's timeline for withdrawing American troops from Afghanistan and told Fox News' Sean Hannity that the surge of migrants crossing the U.S.-Mexico border could "destroy our country" -- the former president's focus remains primarily on himself.

"He hates being off the A block," said a person close to Trump, using a term that refers to the lead segment in a cable news program. "He's really thinking of running again in 2024 just to get back to that."

The person close to Trump's operation said that while his TV consumption has declined since he left office -- a byproduct of him no longer being surrounded by televisions in the Oval Office or aboard Air Force One -- he still reads The New York Times, the Wall Street Journal and the New York Post each morning and regularly marks up articles about his achievements or policies to send to aides and advisers.

And when an unflattering story pops up, he is quick to pick up the phone to complain to friends.

"He'll usually call when there are some bad polls saying something about him or that he feels are out of whack," Trump pollster John McLaughlin said.

Recently, Trump has initiated discussions about resuming the signature MAGA rallies that fortified his nascent political movement in 2016 and continued throughout his presidency. While he has vowed to travel to Alaska to campaign against Murkowski and is said to be interested in hosting campaign events for some of the candidates he's already endorsed, aides said the logistics are still being worked out but that he could resume rallies as early as May.

"It will definitely be different in terms of the setup, but we got really good at planning these events in 2020, so we will probably use a lot of those same vendors again," said the person close to Trump's post-White House operation.

LIFE AFTER WASHINGTON FOR THE REST OF TRUMP'S FAMILY

While Trump's life has changed dramatically since he left Washington three months ago to pursue the next phase of his political career, so too has his family's.

Most of his adult children, as well as his son-in-law, Jared Kushner, have taken a break from the spotlight to provide private counsel to their father or focus on their own families. Several Trump aides who have spent the past few months shuttling between Washington and Mar-a-Lago said Ivanka Trump and Kushner, who purchased a $30 million waterfront lot in Miami shortly before leaving the White House, are the most withdrawn.

Once a prolific over-sharer on social media, with frequent video posts about everything from the child tax credit to workforce campaigns and hundreds of photographs of herself, Ivanka Trump, like her dad, has spent the past 100 days in relative online silence. Kushner, meanwhile, has popped in and out of his father-in-law's orbit as he devotes much of his time to writing a book about his tenure inside the West Wing and preserving the Middle East peace treaties he helped negotiate during the Trump presidency.

"She wants to spend as much time as she can with her family after a few very busy years," said a person familiar with Ivanka's new life in Miami, adding that Trump's elder daughter continues to be a "hands-on mom."

Likewise for Trump's wife and former first lady Melania Trump, whose life outside the East Wing has changed both very much and not at all. People familiar with her activities say she continues to do what she wants when she wants and is not beholden to the norms of conventional post-first lady duties in the same way she conformed to traditions while her husband was in office.

Though she established her own official office with at least three staffers, the most that has come out of it appears to be a stylized logo reminiscent of a presidential seal. She has not made any official appearances since leaving Washington, nor has she announced plans for a memoir -- a popular post-White House activity for former first ladies.

"She's not a presence at Mar-a-Lago at all. She's not mingling with people and rarely interacts with her husband's staff," said a person close to the couple.

What has primarily changed for her, 100 days out, is her environment. Far from the sprawling White House complex, she and Trump share a large suite of rooms at the 17-acre Mar-a-Lago property, though she maintains her own personal office. She makes frequent trips to the on-site spa -- with one person telling CNN she sometimes goes for treatments twice a day -- and spends her afternoons with the couple's son, Barron, now 15.

Three people familiar with Trump's dinnertime appearances say she appears "happy and relaxed" when they have seen her, and that she smiles and gives a wave as other dinner patrons rise from their seats to applaud the arrival of the former first couple to the dining area. She likes the Dover sole and a Diet Coke with no ice, and two of the people note she is often joined by her parents, Viktor and Amalija Knavs, who spend weeks at a time at the South Florida club in their own personal suite, which functions as their seasonal home.

The only Trump relative whose involvement in politics has seemingly increased since the former President left office is that of his eldest son, Donald Trump Jr., who recently closed on a home in Jupiter, Fla., with his girlfriend, Kimberly Guilfoyle, and has become a trusted adviser to his father on political strategy and candidate endorsements.

Trump Jr. and Guilfoyle purchased the 11,000-square-foot home in the Admiral's Cove development for US$9.7 million and are expected to move in shortly, according to a source. Trump's ex-wife, Vanessa Trump, spends a substantial part of the year with the couple's five children in Jupiter, which also happens to be a 40-minute drive from Mar-a-Lago. It is unclear if Trump Jr., who recently returned from a hunting trip in Alaska, will become a regular presence at his father's Bedminster golf club once the former President relocates for the summer. So far, he has stayed in touch with his father mostly by phone, with occasional appearances at his resort in Palm Beach.