President Trump Donald John TrumpHR McMaster says president's policy to withdraw troops from Afghanistan is 'unwise' Cast of 'Parks and Rec' reunite for virtual town hall to address Wisconsin voters Biden says Trump should step down over coronavirus response MORE will address a joint session of Congress for the first time on Tuesday night, and Republican insiders say he may not be in the mood to play nice.

Trump won election as the consummate outsider; his victory came in the face of considerable skepticism from Republicans on Capitol Hill, who often shrank from his flamboyant pronouncements and abrasive personal style.

Now, just over a month into his presidency, Trump is coming to Congress on a mission to ensure that his campaign promises become law.

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“It’s easily the most important speech of his young presidency,” said Alex Conant, who worked on the presidential campaign of one of Trump’s 2016 GOP primary rivals, Sen. Marco Rubio Marco Antonio RubioFlorida senators pushing to keep Daylight Savings Time during pandemic Hillicon Valley: DOJ indicts Chinese, Malaysian hackers accused of targeting over 100 organizations | GOP senators raise concerns over Oracle-TikTok deal | QAnon awareness jumps in new poll Intelligence chief says Congress will get some in-person election security briefings MORE of Florida. “So far, he has spoken a lot to his base, but he has not spoken publicly to Congress, and he has put very little pressure on them.”

John Feehery, a Trump-supporting strategist and a former aide to Republican leaders on Capitol Hill, encouraged the president to take the fight to Congress.

“The president needs to make a bold and stark case for his legislative agenda. He shouldn't play nice or expect to get a favorable reception,” said Feehery, who is also a columnist for The Hill. “This is his chance to tell the American people to lobby the Congress on his behalf and he shouldn't mince words.”

Aides and allies to Trump are behind that approach.

“The audience that the president is speaking to is the American people,” said one longtime Trump ally. “That is always his audience.”

During last year’s election campaign, Trump had especially frosty relations with Speaker Paul Ryan Paul Davis RyanAt indoor rally, Pence says election runs through Wisconsin Juan Williams: Breaking down the debates Peterson faces fight of his career in deep-red Minnesota district MORE (R-Wis.). Ryan refused to campaign for the GOP nominee in the final weeks of the presidential race and declined to encourage his colleagues to do so. When Trump attacked a judge in a Trump University lawsuit over his Mexican heritage last summer, Ryan called it the “textbook definition of a racist comment.”

Ryan has long since made his peace with Trump and will now be sitting behind the president during his big national address. Touring a section of the border with Mexico earlier this week, the Speaker suggested he would keep Congress on board with Trump’s plan to make immigration controls stricter — though he did not specifically mention the president’s pledge to build a border wall, which Trump reiterated in his address to the Conservative Political Action Conference on Friday.

“Congress is committed to securing the border and enforcing our laws,” Ryan said in a statement, “and together with the Trump administration we will get this done.”

Many Republican strategists believe there is still considerable ambivalence about Trump among GOP lawmakers, however.

Rick Tyler, who worked for Sen. Ted Cruz Rafael (Ted) Edward CruzLoeffler calls for hearing in wake of Netflix's 'Cuties' Health care in the crosshairs with new Trump Supreme Court list 'Parks and Rec' cast members hosting special reunion to raise money for Wisconsin Democrats MORE (Texas) in last year’s Republican primary, asserted that Republican lawmakers who are fully on board with Trump are in the minority.

More of them “like what he is proposing substantively but not how he conducts himself stylistically,” Tyler asserted.

One key question is how effective it would be for Trump to adopt a combative approach in the speech. His appeal to voters who were discontented with the political system was a big part of his shock win last November. But he now needs Congress to put his campaign promises into action.

Congress will determine whether Trump’s frequent promise to repeal and replace the Affordable Care Act will come true. The border wall with Mexico has been estimated to cost up to $21 billion — money that Congress will have to appropriate. Other key issues, including tax reform, also rest in lawmakers’ hands.

Trump skeptics, including Tyler, argue that the president would be foolish to be overly confrontational with Congress.

Frontal attacks, the strategist said, “would be mere political posturing.”

“It doesn’t move the ball toward the goal of legislative action,” he added. “It’s a lot of clanging of gongs and cymbals, but it doesn’t mean very much.”

Since the election, Vice President Pence — a former six-term congressman from Indiana — has played a key role in trying to soothe lingering tensions between the White House and Republicans on Capitol Hill. The White House’s director of legislative affairs, Marc Short — himself a longtime Pence aide — has also been central to that effort.

The Trump ally argued that relations between the administration and Republicans in Congress are better than is generally understood.

“I don’t think there is any repair work to be done, no,” the source insisted. “I think it is going to be a very friendly environment. You have to remember there are constant communications between the White House and the Hill now.”

Conant asserted that Trump has the Republican grassroots largely on his side and that he can leverage that power in his dealings with Congress.

“Congress’s natural state is gridlock,” he said. “It only does big things when it feels political pressure from the public and the other end of Pennsylvania Avenue.”

He added, “If President Trump talks about his agenda — instead of his election victory — I think it will be very well received.”

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