The Memo: Can Trump run as an outsider?

President TrumpDonald John Trump5 things to know about Boris Johnson Conservatives erupt in outrage against budget deal Trump says Omar will help him win Minnesota MORE is running for reelection as an outsider candidate. But it’s a knotty challenge for someone who holds the world’s most powerful office.

Trump’s speech in Orlando, Fla., on Tuesday, which officially launched his 2020 bid, was rife with rhetoric portraying himself — and by extension his supporters — as victims of nefarious elites.

The president said that he and his allies were besieged by a “permanent political class” and “an unholy alliance of lobbyists and donors and special interests.”

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“Our patriotic movement has been under assault from the very first day,” Trump insisted at one point. Moments before, he told the crowd, “the swamp is fighting back so viciously and violently.”

It’s the kind of language that makes Democrats roll their eyes. Trump, they note, is a billionaire property developer, born into wealth, who won the presidency on his first attempt — yet he portrays himself as the tribune of “the forgotten men and women of our country” whom he invoked in his January 2017 inaugural address.

But Trump’s unconventionality might, in itself, help him retain some kind of outsider cachet in a way that is unusual for an incumbent president.

“For any other president, yes, it is a challenge,” said Alex Conant, a Republican strategist who worked for Sen. Marco RubioMarco Antonio RubioAna Navarro lashes out at Rubio for calling outrage over Trump's 'go back' tweet 'self righteous' US-Saudi Arabia policy needs a dose of 'realpolitik' Media cried wolf: Calling every Republican a racist lost its bite MORE (R-Fla.) in the 2016 presidential primaries.

“But Trump is unlike any other president. Trump has been at war with the establishment since the moment he set foot in the White House,” he said.

It is certainly true that Trump was viewed with suspicion by the Republican Party from the time he began his presidential run — and that his language and attitudes are viewed with distaste by much of the Beltway political class.

But dislike for Trump’s personal antics is hardly confined to D.C. elites.

A Pew Research Center poll in March showed pluralities of the public believing that he was not “trustworthy,” “even-tempered” or “well-informed.”

For all Trump’s supposed concern with less affluent Americans, 56 percent of the respondents in the Pew poll said they did not believe he cared about “people like me,” whereas just 40 percent said he did care.

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The GOP has largely made peace with him, with former rivals including Sens. Lindsey GrahamLindsey Olin GrahamGraham says he will call Papadopoulos to testify GOP group defends Mueller ahead of testimony The Hill's Morning Report — Mueller Time: Dems, GOP ready questions for high-stakes testimony MORE (S.C.) and Rand PaulRandal (Rand) Howard PaulThe Hill's Morning Report — Trump applauds two-year budget deal with 0 billion spending hike The Hill's Morning Report — Mueller Time: Dems, GOP ready questions for high-stakes testimony This week: Mueller dominates chaotic week on Capitol Hill MORE (Ky.) becoming enthusiastic supporters, congressional dissenters such as former Rep. Mark SanfordMarshall (Mark) Clement SanfordTrump faces new hit on deficit Sanford calls for 'overdue conversation' on debt as he mulls Trump challenge Trump primary challenger Bill Weld responds to rally chants: 'We are in a fight for the soul of the GOP' MORE (R-S.C.) having been defeated in primaries and Trump now in firm control of the party apparatus.

Skeptics also point to both policies and personnel — from the steep cut in the corporate tax rate in 2017 to the 16-month run of the ethically challenged Scott PruittEdward (Scott) Scott PruittOvernight Energy: EPA halts surprise inspections of power, chemical plants | Regulators decline to ban pesticide linked to brain damage | NY awards country's largest offshore wind energy contracts EPA allows continued use of pesticide linked with brain damage Overnight Energy: Trump officials gut DC staff for public lands agency to move West | Democrats slam EPA over scientific boards | Deepwater Horizon most litigated environmental issue of decade MORE as head of the Environmental Protection Agency — as evidence that the swamp has remained undrained under Trump.

But Trump allies are insistent that the president’s feel for the cultural mores of blue-collar America remains a potent and underrated political weapon.

“He is certainly an outsider to the political establishment. They still don’t get him and he is not coming around to their way of thinking,” said Barry Bennett, who worked as a senior adviser to Trump’s 2016 campaign. “He may live inside the gates but he does not live inside the establishment. … I don’t know anyone who believes he has become some kind of Georgetown socialite.”

Michael Caputo, a longtime Trump friend, insisted, “I have never ever met anyone, any Trump supporter, who believes anything else besides the fact that he’s an outsider.”

There is clearly a political dividend to be gained if Trump can hold onto his outsider image.

In the recent past, voters in presidential elections have often chosen the candidate seen as less steeped in the ways of Washington.

Former President Obama won election twice as a change agent, initially winning the White House as the first black president and then securing a second term over GOP nominee Mitt RomneyWillard (Mitt) Mitt RomneyDemocrats should rise above and unify against Trump's tweets Trump steps up attacks on 'Squad' after post-rally furor Media cried wolf: Calling every Republican a racist lost its bite MORE, the personification of a genteel Republican establishment.

Former President George W. Bush had only a tenuous claim to outsider status, given he was the son of a president — yet his campaign was able to paint then-Sen. John KerryJohn Forbes KerryJohn Kerry: Pressley's story 'more American than any mantle this president could ever claim' Schumer to donate Epstein campaign contributions to groups fighting sexual violence Trump threatens Iran with increased sanctions after country exceeds uranium enrichment cap MORE (D-Mass.) as a creature of Washington in the 2004 presidential election.

Before that, former President Clinton used his down-home Arkansas image as a weapon against an incumbent president, Bush’s father, George H.W Bush, and then won a second term over another GOP establishment favorite, then-Sen. Bob Dole (Kan.).

Independent observers acknowledge that Trump’s style, divisive though it is, could help him be seen as much more of a disruptor even than these recent predecessors.

“It’s almost impossible for an incumbent to run as an outsider, but Trump has held onto that credential,” said Tobe Berkovitz, a Boston University professor who specializes in political communications. “He is parlaying that into how he sees himself — running against the Democrats, the media, the elites.”

Republicans, meanwhile, argue that Trump’s outsider image could be especially useful if Democrats pick former Vice President Joe BidenJoe BidenPoll: Biden leads 2020 Democratic field by 15 points, followed by Sanders and Warren Booker takes swipe at Biden criminal justice reform plan Panel: Has Joe Biden been wrong on everything for 40 years? MORE as their nominee.

Biden, in their telling, is much easier to brand as a creature of Washington given his decades in the Senate. There will be a different challenge if Democrats instead choose one of Biden’s rivals who is a fresher face on the national political scene, such as Sen. Elizabeth WarrenElizabeth Ann WarrenPoll: Biden leads 2020 Democratic field by 15 points, followed by Sanders and Warren Warren introduces bill to cancel student loan debt for millions Democrats, advocacy groups urge Pompeo to abolish new 'unalienable rights' commission MORE (D-Mass.) or Sen Kamala HarrisKamala Devi HarrisPoll: Biden leads 2020 Democratic field by 15 points, followed by Sanders and Warren Democrats, advocacy groups urge Pompeo to abolish new 'unalienable rights' commission Biden announces plan to counteract mass incarceration MORE (D-Calif.); or more radical, such as Sen. Bernie SandersBernie SandersPoll: Biden leads 2020 Democratic field by 15 points, followed by Sanders and Warren Warren introduces bill to cancel student loan debt for millions Democrats, advocacy groups urge Pompeo to abolish new 'unalienable rights' commission MORE (I-Vt.).

Trump, billionaire Manhattanite though he may be, has long used the idea that he is sneered at by a snobbish elite to his own advantage.

On Tuesday, he told his supporters that Democrats “want to destroy you.”

It was a stark and visceral remark even by Trump’s standards.

But, after his 2016 victory, even his critics can’t be so sure it won’t work.

The Memo is a reported column by Niall Stanage, primarily focused on Donald Trump’s presidency.