Trump’s and Biden’s Advisers Had the Same Problem: a Stubborn Candidate

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At times, the conversation sounded an awful lot like hostages recounting their monthslong trauma. Their opinions were unlikely to be heeded, and rarely solicited. There was little they could do to change the conditions, so they made the best of the moment. It sounded like a day-by-day strategy of survival, one borne of necessity and endured with unenviable grit.

The people recounting their months of powerless standing were the very top aides to the current President, and his predecessor, who is soon to also be his successor. And, with an unnerving consistency, it sounded at times as if they were all completely overtaken by two aged nominees who had zero interest in hearing from the very operatives tasked with running their billion-dollar campaigns. These were some of the sharpest taskmasters in the business who seemed sidelined by circumstance. It was in many ways the distillation of a campaign cycle that left even the most plugged-in politico feeling deflated.

Listening this month at Harvard to the top aides to these two temperamentally distinct Presidents recount their experiences —part of the Kennedy School of Government’s tradition of oral histories for those in the rooms where decisions are made—it struck me: maybe these two insular, self-confident men are in some ways mirrored images of each other. That professed confidence in each’s own instincts and indifference to most dissident opinions is how both led the country and made some pretty colossal missteps. Another trait they may also share? A deep insecurity that masks itself with action.

Take the Democrats. Jen O’Malley Dillon, who ran Joe Biden’s 2020 presidential race and served as the deputy chief of staff in the West Wing, was dispatched to reprise the role earlier this year, despite widespread concerns that his age, among other concerns, would keep him from drawing the support he needed. 

Nonetheless, everyone moved ahead, trying to make the best of it. It was not like Biden asked them if he should be running in the first place, and it’s not likely he would have heeded any staffer’s qualms about his fitness or electability. Even Biden’s closest advisers—the men who have been with him a half-century at this point—aren’t known to offer tough talk when they walk into the Oval. None appeared to have properly prepared for the prospect of an increasingly unreliable Biden imploding on stage as he did, let alone the possibility that he would not be on the ballot come Election Day. There was no escape or easing of the pain.

The campaign went into overdrive, looking for an alternative plotline. They sent Biden to North Carolina, where he delivered a much-improved pitch. Privately, folks like O’Malley Dillon worked around the clock to calm skittish donors and activists. New TV ads were cut, hoping to stop the panic. No one credibly thought there was a ripcord away from Biden.

"Something visual happened in front of people's eyes. The only way to combat that is to give them something visual. And the only visual play you have at that point is putting Joe Biden in front of as many people as possible, which is what we tried to do,” said Quentin Fulks, the principal deputy campaign manager. “And so, when he caught COVID, it's almost like a dagger."

It’s well known by now what came next. Biden retreated to Delaware to isolate and recover. Democrats started to snowball in their calls for Biden to re-evaluate his next steps. Money dried up. Rank-and-file Democrats seized up. Fulks likened it to a “slow bleed.” 

But to hear the top ranks of the Biden campaign profess, there were zero credible conversations to prepare for the dramatic next steps of Biden bowing out of the race and effectively swapping his name with Vice President Kamala Harris on ballots. (“Not one ounce,” O’Malley Dillon said.) Before that historic decision was made, there wasn’t even a conversation about it between Biden and the people he had tasked with winning him another four years in the job. The 82-year-old Biden simply phoned this campaign chair and its manager, Julie Chavez Rodriguez, to tell them he was ending it.

Across the table, the Trump team listened carefully. Although they had plenty of bile to hurl across the table—”flawless execution,” Trump campaign co-manager Chris LaCivita mocked at one point—they also offered up their own limitations in dealing with a 78-year-old figure set in his ways. They couldn’t call it “debate prep,” even though they were treating conversations with the boss like the spoon of vegetable puree fed to an infant by masquerading it as an airplane. They never dared to describe things in absolutes, knowing Trump would reject something if he was told there were no other options. “Worry about what you can control. On the campaign, I worried about what I could control,” LaCivita said. “He was not one of them.”

Here, it’s worth noting that Trump ultimately won, and both his Biden’s tendencies may show signs of a confident leader, someone so sure of his footing that doubt is for other people to worry about. People who ooze humility don’t run for President, after all. You have to have some swagger to think you are the right person to lead the other 335 million Americans. 

But most Presidents have an inner circle of trusted hands who can chip away some of that bravado. Sure, Biden has a handful of close confidants but has not been exactly solicitous for advice since winning the White House. He will phone friends for gut checks, but they get the sense he’s looking more for an atta’boy than anything else, according to multiple sources who keep tabs on their pal from a comfortable distance. He certainly was not looking to entertain the tough questions about his viability for re-election, and he did not even bother to ask the two top operatives he put in charge of his political fortunes. After his debate collapse, it’s not clear he was even open to such a conversation.

Barack Obama came across to his foes as the principle of arrogance. But he wisely kept minister-without-portfolio Valerie Jarrett in the West Wing for eight years to keep him grounded. George W. Bush has his Texans—native and adoptive—who would call him out for getting too big for his britches. Bill Clinton’s orbit was full of longtime friends of varying talents who never let the Hope, Ark., native forget his roots. The trio all hired the best-in-class consultants and advisers to handle the practical day-to-day grind, and usually persuaded the bosses that the empirical evidence offered a rational prescription. Objectively, each of those three oversaw highs and lows, but they all reached their best moments when they worked in concert with advisers who could offer their candid—if flawed in hindsight—counsel. Their worst days? When they didn’t heed the warnings against hubris. And, for those three, you cannot undervalue the importance of their spouses in occasionally setting them right. 

Biden is now on his glidepath toward retirement. In six weeks, he will have the luxury of doing as he pleases with little consequence for the global order. Trump, on the other hand, is heading back to Washington with some of the big ambitions, a better understanding of government than when he first arrived here in 2017, and grievances to spare. As he assembles a Cabinet and senior staff, it’s abundantly clear he is casting enablers in major roles. It’s not readily apparent that he has now—or had in his first term—a guardrail against impulses. The independence in both men got them to their electoral fates essentially as solo acts. But if Biden’s insistence on running again has any lesson for Trump, it’s that major decisions like that cannot be responsibly reached as a one-man show.

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