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President Donald Trump speaks during a meeting on women in healthcare, Wednesday in the Roosevelt Room of the White House in Washington. From left: Parmis Khatibi, Trump, and administrator of the Centers for Medicare and Medicaid Services Seema Verma.Evan Vucci/The Associated Press

David Shribman is executive editor of the Pittsburgh Post-Gazette.

Big struggle, big gamble, big stakes.

Eight years ago, Barack Obama engaged in a similar struggle, making his signature overhaul of the U.S. health-care system an early priority. He went to the White House with piles of political capital and spent almost all of it on the plan that now goes by the name of Obamacare.

Now Donald Trump, who prides himself on doing exactly the opposite of what Mr. Obama did, is reprising the struggle and the gamble – with even bigger stakes.

Mr. Trump has just passed the two-month mark in his presidency and, by his own (dangerous) admission, is making a big bet on the repeal and replacement of Obamacare – especially risky given the context of new attacks on his credibility following FBI assertions there was no evidence that Mr. Obama wiretapped him. That renders the House vote on the health overhaul – currently scheduled for Thursday, though congressional leaders might postpone the vote in light of lingering conservative doubts about the legislation – a major test of the Trump agenda.

David Shribman: Obamacare repeal: A political path never taken

The President, who 30 years ago – the presidency not even a glint in the tycoon's eyes – wrote a book called The Art of the Deal, is dealing from the White House, with a great deal at stake.

Mr. Trump's reputation as a master strategist.

The fourth sentence in The Art of the Deal is telling: "Deals are my art form." Hardly anyone was watching as he made real estate and casino deals across the country and the world. Everyone who has ever been to a doctor is watching this one.

In this episode, Mr. Trump is employing pride, pressure and his prerogatives as President. He is telling Republicans that his and their reputations are at stake. He is making and promising their demise in the 2018 midterm elections if they oppose the repeal bill. And he is using his trademark tool of the Big Promise: This will be better, cheaper, cleaner.

The Republicans' reputation as the natural governing party.

This argument, familiar to Canadians who have heard the Liberals make this claim for decades, was polished during the era 1969-93, when Republicans controlled the White House with the exception of a four-year Jimmy Carter interregnum from 1977 to 1981.

But now the Republicans have not only the White House but also both houses on Capitol Hill. They also have dozens of votes in the House to repeal Obamacare behind them, scores of campaign promises to eliminate the insurance mandate and a high-profile capital showdown to do so. They know they will get no Democratic votes, as the original Obamacare legislation won no Republican votes. It is all on them. If they fail, or falter, their self-proclaimed identity will be undermined.

Just Wednesday morning, the editorial page of The Wall Street Journal, regarded as the voice not only of mainstream Republicanism but also of the conservative movement, set forth the challenge. The vote, the newspaper's editorialists said, "is a linchpin moment for this Congress, and a test of whether the GOP can deliver on its commitment to voters."

Who runs the Republicans, the President or the conservatives?

This question has been lingering in the GOP air for more than a year. During the primary campaign, candidates such as Senator Marco Rubio of Florida and Ted Cruz of Texas assailed Mr. Trump as a faux conservative, not only because of his early identification with Democrats and his support for abortion rights, but also because in his current populist identity, he seldom articulated conservative principles.

More recently, Mr. Trump's 2017 program for a massive increase in road, bridge, tunnel and airport construction appeals more to liberals (who like these sorts of spending programs for the jobs they provide and as symbols of positive government intervention) than conservatives, who are wary of any spending programs and whose inclination is to punt these sorts of programs to the states.

In the final hours before the vote, Mr. Trump's biggest challenge is to win the support of conservatives, who believe the current legislation does not go far enough because it still includes federal subsidies.

What is the profile of House Speaker Paul Ryan?

The Wisconsin Republican is the steward of this legislation, which transforms the vote on the bill into something of a referendum on a Speaker who didn't want the job in the first place, whose image as the intellectual avatar of modern Republicanism is being challenged and whose support among the activist wing of his party is tenuous.

That is without saying that Mr. Ryan has – to employ a favourite Capitol Hill understatement meant to suggest deep suspicion if not contempt – minimal high regard for the President. Just this month, a private tape of Mr. Ryan's true feelings about Mr. Trump during the campaign was released. "I am not going to defend Donald Trump – not now, not in the future," the Speaker said in an October, 2016, conference call. Now he and the President are wary allies in the biggest test of the administration thus far – and perhaps all year.

Can Mr. Trump really punish Republicans who break from him?

He has warned possible Republican apostates: "I'm gonna come after you." He may, but it may not matter.

Presidents rarely make that sort of threat. They need the allegiance of every lawmaker in their party, if not now then later. The cautionary historical lesson comes from Franklin Roosevelt, who tried to purge conservative-leaning Democrats in the midterm congressional elections of 1938. Every one of Mr. Roosevelt's targets survived his primary challenge.

But there is a broader lesson here. Mr. Roosevelt wanted to rid the Democrats of conservatives who opposed his New Deal domestic programs. Later he benefited from their survival; they were the very lawmakers who helped him rearm the country as the Second World War began and as isolationist sentiment spread in the United States. Opponents once, they were allies later – as some of these health-care skeptics may be.

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