The Memo: Can Trump run as an outsider?

President TrumpDonald John TrumpNational Archives says it altered Trump signs, other messages in Women's March photo Dems plan marathon prep for Senate trial, wary of Trump trying to 'game' the process Democratic lawmaker dismisses GOP lawsuit threat: 'Take your letter and shove it' 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 RubioApple under pressure to unlock Pensacola shooter's phones Senators offer bill to create alternatives to Huawei in 5G tech Surging Sanders draws fresh scrutiny ahead of debate 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 GrahamSenate GOP mulls speeding up Trump impeachment trial Democratic group plans mobile billboard targeting Collins on impeachment Paul predicts no Republicans will vote to convict Trump MORE (S.C.) and Rand PaulRandal (Rand) Howard PaulGOP threatens to weaponize impeachment witnesses amid standoff Paul predicts no Republicans will vote to convict Trump Graham on impeachment trial: 'End this crap as quickly as possible' MORE (Ky.) becoming enthusiastic supporters, congressional dissenters such as former Rep. Mark SanfordMark SanfordTrump challenger Bill Weld rules out 2020 independent bid Judge throws out lawsuit against South Carolina GOP for canceling 2020 primary The Hill's Campaign Report: Late bids surprise 2020 Democratic field 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 PruittEPA employees push 'bill of rights' to protect scientific integrity EPA's independent science board questions underpinnings of numerous agency rollbacks Overnight Energy: Rate of new endangered species listings falls | EPA approves use of 'cyanide bombs' to protect livestock | Watchdog says EPA didn't conduct required analyses 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 RomneyRepublicans will pay on Election Day for politicizing Trump's impeachment Bring on the brokered convention GOP threatens to weaponize impeachment witnesses amid standoff 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 KerryBring on the brokered convention 18 progressive groups sign unity pledge amid Sanders-Warren feud Mellman: Democrats — Buckle up for a wild ride 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 BidenSanders to headline Iowa event amid impeachment trial Hillicon Valley: Biden calls for revoking tech legal shield | DHS chief 'fully expects' Russia to try to interfere in 2020 | Smaller companies testify against Big Tech 'monopoly power' Hill.TV's Krystal Ball on Sanders-Warren feud: 'Don't play to the pundits, play to voters' 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 WarrenSanders to headline Iowa event amid impeachment trial Hill.TV's Saagar Enjeti rips Sanders over handling of feud with Warren On The Money — Presented by Wells Fargo — Sanders defends vote against USMCA | China sees weakest growth in 29 years | Warren praises IRS move on student loans MORE (D-Mass.) or Sen Kamala HarrisKamala Devi HarrisSanders defends vote against USMCA: 'Not a single damn mention' of climate change The Hill's Morning Report — President Trump on trial Overnight Energy: Schumer votes against USMCA, citing climate impact | Republicans offer details on their environmental proposals | Microsoft aims to be carbon negative by 2030 MORE (D-Calif.); or more radical, such as Sen. Bernie SandersBernie SandersSanders to headline Iowa event amid impeachment trial Hill.TV's Saagar Enjeti rips Sanders over handling of feud with Warren On The Money — Presented by Wells Fargo — Sanders defends vote against USMCA | China sees weakest growth in 29 years | Warren praises IRS move on student loans 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.