President TrumpDonald John TrumpSenate advances public lands bill in late-night vote Warren, Democrats urge Trump to back down from veto threat over changing Confederate-named bases Esper orders ‘After Action Review’ of National Guard’s role in protests MORE is facing a crucial 48 hours.

His favored candidate in Tuesday’s GOP Senate runoff in Alabama, Sen. Luther StrangeLuther Johnson StrangeThe biggest political upsets of the decade State ‘certificate of need’ laws need to go GOP frets over nightmare scenario for Senate primaries 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.

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The vote might not even take place, however, after Sen. Susan CollinsSusan Margaret CollinsRepublicans prepare to punt on next COVID-19 relief bill Trump tweets spark fresh headache for Republicans Trump’s tweet on protester sparks GOP backlash  MORE joined Sens. Rand PaulRandal (Rand) Howard PaulRand Paul introduces bill to end no-knock warrants Louisville passes ‘Breonna’s Law’ banning no-knock warrants Rand Paul aide joins Trump campaign, RNC fundraising group MORE (R-Ky.) and John McCainJohn Sidney McCainThe Hill’s Campaign Report: Bad polling data is piling up for Trump Cindy McCain ‘disappointed’ McGrath used image of John McCain in ad attacking McConnell Report that Bush won’t support Trump reelection ‘completely made up,’ spokesman says 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 McConnellSenate advances public lands bill in late-night vote GOP senator to try to reverse requirement that Pentagon remove Confederate names from bases No, ‘blue states’ do not bail out ‘red states’ 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 SchumerOvernight Health Care: US showing signs of retreat in battle against COVID-19 | Regeneron begins clinical trials of potential coronavirus antibody treatment | CMS warns nursing homes against seizing residents’ stimulus checks Schumer requests briefing with White House coronavirus task force as cases rise Schumer on Trump’s tweet about 75-year-old protester: He ‘should go back to hiding in the bunker’ 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.