WASHINGTON — For many who answered to President Donald Trump, the job was a risk-reward proposition like no other.
There was a chance to win his favor and shape national policy. And there was the possibility of running afoul of the boss and getting publicly humiliated.
Cabinet secretaries came and went in a Trump administration marked by head-spinning turnover.
Former advisers churned out memoirs detailing their frustrations with Trump, who in turn used his massive public platform to shower them with insults.
Should he return to the White House, Trump would need to build a leadership team once again — a challenge made more daunting by his track record and his ability to win Senate confirmations for the loyalists he would need to carry out his orders.
In preparation, Trump advisers are preparing to take charge of the executive branch if he wins in November, a transition process that is customary for presidential nominees. Allies are compiling lists of potential job candidates and building dedicated teams that would guide any nominees toward Senate confirmation.
The transition work is happening quietly, outside of public view and away from the campaign trail. Not wanting to tempt fate by acting as if the election is already won, Trump has kept some distance from his own transition operation, said a person familiar with the planning, who, like others in this article, was granted anonymity to speak freely.
After he defeated Hillary Clinton in 2016, Trump remarked that she had assembled an effective transition team but lost anyway “because everyone was in Washington measuring the drapes,” a person familiar with Trump’s comments at the time said.
Yet Trump’s own transition that year was famously chaotic. Former New Jersey Gov. Chris Christie led the effort, only to be pushed aside and see much of his work tossed out after Trump’s stunning upset victory.
This time, several dozen people are working on a potential Trump transition and expect to complete a thorough vetting of possible Cabinet picks before the election, the person familiar with the planning said.
They’ve had to move quickly. Trump’s campaign named his transition leaders just last month, a shortened timetable for accomplishing its work, an expert on presidential transitions said.
“Relative to modern practice, the Trump team was slow off the mark in announcing their transition operation,” said Max Stier, president and CEO of the nonprofit Partnership for Public Service. “They were the presumed nominee for quite some period, and the normal timetable would be to start their work in the spring, as opposed to the end of summer or beginning of fall.”
“With the team that they selected, it’s not clear that they have the governmental experience that is fundamental to success,” Stier added. “In thinking about the expertise you need, deep expertise is at the top of the list. The names [of people running the Trump transition] speak for themselves.”
Vice President Kamala Harris’ advisers, too, are preparing for a possible victory in November, as both campaigns look to take the fullest advantage of the first 100 days in office, when a new president’s political capital is at its peak.
Their tasks differ in that Harris is already part of an incumbent Democratic administration and has the option of keeping officials in place if she chooses.
Trump would be creating a Cabinet from scratch. His distinct challenge would be to find people who are loyal to him — always a priority for Trump — but who are also sufficiently respected in their fields to win Senate confirmation.
“He’d have no difficulty staffing his Cabinet,” Sen. Mitt Romney, R-Utah, said in an interview. “The question would be whether they are people of stature or capacity and are up to the job required and whether they could be confirmed.”
“I think it’s unlikely he would get a group of generals like he did last time,” Romney added, referring to James Mattis, H.R. McMaster and John Kelly, all of whom were generals before they took high-ranking positions in the Trump administration. (Romney, a Trump critic, is retiring from the Senate and won’t be in office next year to vote on the next president’s nominees.)
‘Fishing for them in a smaller pond’
Finding people to serve could prove difficult if potential candidates didn’t like what they saw of Trump’s presidency or feared his ire.
Trump has called one of his former attorneys general, William Barr, a “gutless pig” and another, Jeff Sessions, “weak and ineffective.” He labeled one defense secretary, Mark Esper, “a lightweight” and another, Mattis, “the world’s most overrated general.”
“There are a lot of good people out there, but Trump would be fishing for them in a smaller pond,” said Marc Short, who was the first legislative affairs director in the Trump White House and later chief of staff to Vice President Mike Pence.
“He was entertaining,” Short said of Trump. “He’s gregarious and friendly to staff. But he has a way of getting information from a lot of different sources. So you always had to adapt and stay on your toes.”
A Trump ally, Sen. Lindsey Graham, R-S.C., said he was confident that Trump would surround himself with capable officials.
“This idea that somehow he won’t be able to have a good team is ridiculous,” Graham said in an interview. “He’ll have a really good team.”
Among those Trump is said to be considering for secretary of state are Republican Sens. Marco Rubio of Florida and Bill Hagerty of Tennessee, as well as Robert O’Brien, a former White House national security adviser, people familiar with the planning said.
A crucial position in another Trump presidency would be attorney general. After he left office, state and federal prosecutors filed multiple criminal charges against Trump stemming from his efforts to reverse the 2020 election results. He has pleaded not guilty in all cases. Those indictments aren’t likely to be resolved before the next president is sworn in. Whether Trump or Harris wins, the next attorney general will inevitably be dealing with pending Trump cases.
Top candidates for Trump’s attorney general include Sen. Mike Lee, R-Utah, and Ken Paxton, the attorney general of Texas.
“When I look back at his first term as president — and I hope his only term as president — I’m concerned about the type of person he chooses and whether or not they have any backbone, because he’s going to come up with some outlandish ideas again, I’m sure, if he has a chance,” said Sen. Dick Durbin, D-Ill., chairman of the Judiciary Committee, which will vote on whether to confirm an attorney general nominee.
Potential defense secretary picks include Sen. Tom Cotton, R-Ark., Rep. Mike Waltz, R-Fla., and Mike Pompeo, who was secretary of state and CIA director in Trump’s term, according to people familiar with transition planning.
Another post that would loom large in a Trump administration is that of secretary of homeland security. Whoever serves would be carrying out Trump’s directive to stanch illegal immigration and carry out what his campaign calls “the largest deportation operation in American history.”
A leading contender for the top homeland security post is Thomas Homan, a former acting director of Immigration and Customs Enforcement in the Trump administration.
In July, Homan gave a speech at the Republican National Convention in Milwaukee. Past presidents he worked for promised to “secure the border,” Homan told the crowd, adding that “Trump actually did it.”
‘I like acting’
Heading Trump’s transition team are Howard Lutnick, chairman and CEO of Cantor Fitzgerald, a financial services firm, and Linda McMahon, who ran the Small Business Administration during Trump’s presidency. Lutnick’s main role is personnel, while McMahon is more focused on policy priorities, two people familiar with their work said.
A Trump ally said the guidance given to Lutnick and McMahon is not to focus on the Cabinet, advisory positions or the top ambassadorships.
“That’s the president’s job,” this person said. “Their responsibility is to be sure that the administration is completely staffed from day one,” meaning the assistant secretaries and the key components of the bureaucracy.
Advisers to Trump’s transition include his sons Donald Trump Jr. and Eric Trump. Late last month, Trump added two more allies to his transition operation: former presidential candidate Robert F. Kennedy Jr. and former Democratic Rep. Tulsi Gabbard of Hawaii.
A senior Trump official said another adviser from the start has been Doug Hoelscher, who is also chair of the America First Policy Institute’s transition project. AFPI is a tax-exempt research group led by a number of former Trump administration officials.
Hoelscher, who was director of the White House Office of Intergovernmental Affairs during the Trump administration, has led AFPI’s efforts to smooth the way for an incoming administration, with Trump-molded policy recommendations and plans for ushering in Trump’s agenda on day one.
A staggering number of variables figure into the staffing of a Trump administration. Plucking someone from the Senate may offer the surest path to Senate confirmation. Yet if Republicans win control of the Senate but secure only a narrow majority, moderates like Lisa Murkowski of Alaska and Susan Collins of Maine could sink a far-right nominee.
Another deterrent to pulling nominees from the House or the Senate is that doing so might eat into slim GOP majorities.
Sessions is a cautionary tale of what can go awry. Sessions, then a Republican senator from Alabama, left to become Trump’s attorney general in early 2017.
It would have seemed that Republicans would hold the seat Sessions vacated, given the state’s deep Republican voting base. But that didn’t happen.
The state’s Republican governor appointed Luther Strange to fill the open seat. Later that year, Strange lost a Republican primary runoff to Roy Moore, the former chief justice of Alabama’s Supreme Court.
Moore, though, faced allegations of sexual misconduct. He went on to lose a special election to Democrat Doug Jones, the first time in 25 years that Alabama had elected a Democrat to the Senate.
“The issue is: Can you drain Congress of their best people when you should have an aggressive agenda in the first 100 days?” a person familiar with Trump’s thinking said.
Trump’s transition team is assembling small teams of people who would help shepherd nominees through to Senate confirmation. As president, he often relied on acting department officials whom the Senate hadn’t confirmed for those roles.
Speaking to reporters in 2019, Trump said, “I sort of like ‘acting.’ It gives me more flexibility. Do you understand that? I like ‘acting.'”
A Brookings Institution report in 2020 asserted, “Rather than identifying qualified individuals who could withstand the scrutiny of the Senate, President Trump has sidelined the chamber’s role and placed loyalists in these critical positions.”
What worries good-government advocates is that he may bypass the Senate confirmation process in a new term, installing more people on an acting basis. His last term showed that it was difficult to block him from appointing acting officials without a Congress that’s prepared to stand up for its own constitutional prerogatives, Stier said.
“The system is being challenged in ways that no one certainly on Capitol Hill previously thought was likely or even imaginable,” he said. “I do think that given past actions by former President Trump, these are good questions to be asking, and [I] will say that the landscape is uncertain as to how the courts or for that matter the Senate might respond.”