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The Memo: Trump faces difficult 48 hours

President TrumpDonald TrumpCaitlyn Jenner says election was not 'stolen,' calls Biden 'our president' Overnight Health Care: FDA authorizes Pfizer vaccine for adolescents | Biden administration reverses limits on LGBTQ health protections Overnight Defense: US fires 30 warning shots at Iranian boats | Kabul attack heightens fears of Afghan women's fates | Democratic Party leaders push Biden on rejoining Iran deal MORE is facing a crucial 48 hours.

His favored candidate in Tuesday’s GOP Senate runoff in Alabama, Sen. Luther StrangeLuther Johnson StrangeThe Hill's Morning Report - Biden assails 'epidemic' of gun violence amid SC, Texas shootings Trump faces test of power with early endorsements Alabama zeroes in on Richard Shelby's future MORE, is running behind ultra-conservative challenger Roy Moore in the polls. A loss for Strange would be seen as a rebuke of Trump by his base.

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The following day, the Senate had been due to vote on the third — and perhaps final — effort to dismantle the Affordable Care Act, also known as ObamaCare.

The vote might not even take place, however, after Sen. Susan CollinsSusan Margaret CollinsTop female GOP senator compares Cheney ousting to 'cancel culture' Utah county GOP censures Romney over Trump impeachment vote House conservatives take aim at Schumer-led bipartisan China bill MORE joined Sens. Rand PaulRandal (Rand) Howard PaulTim Scott sparks buzz in crowded field of White House hopefuls Sherrod Brown calls Rand Paul 'kind of a lunatic' for not wearing mask Overnight Health Care: WHO-backed Covax gets a boost from Moderna MORE (R-Ky.) and John McCainJohn Sidney McCainEx-McSally aide pleads guilty to stealing over 0K in campaign funds DOJ: Arizona recount could violate civil rights laws Cheney fight stokes cries of GOP double standard for women MORE (R-Ariz.) in opposition to the measure.

The three Republican “no” votes make the failure of the push virtually certain.

Prominent figures who were once stalwart supporters of Trump are sharply critical of him on both issues — especially the endorsement of Strange, which they see as a significant miscalculation.

“It would be better if the president would spend half as much time demanding full congressional funding for a [border] wall as he has pushing a mediocre ObamaCare ‘fix’ and an open-borders Senate candidate,” conservative commentator Ann Coulter told The Hill. “His central campaign promise was not to elect John McCain clones to the Senate.”

Roger Stone, the maverick GOP strategist and longtime friend of the president, said Trump had been “conned” into endorsing Strange by moderates in the White House.

Trump endorsed Strange in early August, but there had been persistent rumors in late summer that he was regretting his choice.

Strange is strongly backed by Senate Majority Leader Mitch McConnellAddison (Mitch) Mitchell McConnellManchin, Biden huddle amid talk of breaking up T package Romney: Removing Cheney from House leadership will cost GOP election votes The Hill's 12:30 Report - Presented by Facebook - Biden reverses Trump limits on transgender protections MORE (R-Ky.), with whom Trump has a testy relationship.

Further complicating the picture, Trump’s erstwhile chief strategist, Stephen Bannon, has been a vigorous backer of Moore. Breitbart, the conservative news outlet Bannon runs, has unleashed a fusillade intended to sink Strange.

Some Trump allies bridle at the amount of attention given to Bannon and Breitbart.

Stone noted that he himself had been a longtime Moore backer, even while “the media has reported substantially on Steve Bannon’s support.”

Chris Ruddy, a friend of Trump’s and the chief executive of Newsmax Media, said Monday that, if Moore wins, “the press is going to say this was Bannon defeating Trump, but that won't be really accurate, in my book.”

Trump committed himself to Strange when he traveled to Huntsville, Ala., on Friday to campaign for the incumbent senator.

Trump argued that Strange would be a better candidate in the general election than Moore, who once argued that “homosexual conduct should be illegal” and referred earlier this month to ethnic groups as “blacks and whites fighting, reds and yellows fighting."

Trump also paid tribute to Strange’s loyalty to him. But he tempered his rhetoric to an unusual extent, openly acknowledging that he may have made a mistake in backing Strange and emphasizing that he would campaign “like hell” for Moore if he became the GOP nominee.

Trump allies argue that McConnell has more at stake in Alabama than the president.

This thesis is built upon the idea that McConnell has backed Strange without any of Trump’s ambivalence — and that the president will get another strong supporter in the Senate if the GOP ultimately holds the seat, regardless of whether the winner is Strange or Moore.

“His support on Friday was tepid. He is setting himself up to pivot” from Strange to Moore, said one Republican strategist familiar with White House thinking. “He hasn’t put a lot of his capital on the line and, regardless of the outcome, he will walk away with a supporter.”

But others did not buy the argument that a loss would harm only McConnell.

Michael Steele, a former chairman of the Republican National Committee, said that if Moore wins, “the fact of the matter is that it is a rebuke of McConnell and the president — because you would think that the president’s cachet would be enough to carry Strange.”

On health care, the president seems to be reconciling himself to the prospect of defeat.

In a Monday appearance on the “Rick & Bubba” radio show, he blamed McCain for the reduced chances of the bill passing, adding that it “looks like Susan Collins and some others … will vote against. … We’re going to lose two or three votes and that’s the end of that.”

The previous afternoon, Trump had told reporters at a New Jersey airport that his “primary focus … from the beginning” had been tax reform. On health care, he would only say, “eventually we'll win, whether it's now or later.”

Steele contended that a final, conclusive failure on repeal would add more poison to a relationship between Trump and GOP leaders on Capitol Hill that is already toxic.

“Unfortunately, the result will not be ‘a lesson learned,’ but more recrimination between the White House and Congressional leaders,” he predicted.

The strategist familiar with White House thinking said that Trump would be likely to turn once again toward Democratic leaders if ObamaCare repeal fails.

Trump has recently done deals with “Chuck and Nancy” — Senate Democratic leader Charles SchumerChuck SchumerHouse conservatives take aim at Schumer-led bipartisan China bill There will be no new immigration law under Biden, unless he changes course This week: Congressional leaders to meet with Biden amid GOP reckoning MORE (N.Y.) and House counterpart Nancy Pelosi (Calif.) — on the debt ceiling and, in general terms, on immigration.

For now, however, Trump could be facing two significant defeats in two days. For a president so wedded to the image of himself as the ultimate winner, that is a painful prospect.

Unless, of course, he surprises once again.

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