Washington (CNN)To make a deal, you have to know when it’s time to walk.
President Donald Trump ripped that classic move from his boardroom playbook Thursday night, seeking to splinter the resistance of House Republicans refusing to pass the health care bill that has left his new administration in limbo.
After days of trying to charm members of Congress, Trump gave them an ultimatum: If they don’t vote yes Friday, he will move on and saddle them with the shame of failing to repeal Obamacare, a cherished GOP goal.
If Trump’s decision to call the lawmakers’ bluff delivers victory on Friday, he will establish his authority over the GOP on Capitol Hill and deliver a much-needed victory for a White House under siege.
But if his gamble fails, he will taste a humiliating defeat that suggests that the same GOP infighting that handicapped the party while Democrats held the White House is immune to the outsider shakeup he promised for Washington.
Trump’s bet represents his most audacious risk yet in a presidency built on his own conviction that his superior negotiating skills can unlock an era of congressional inertia and pass laws that will reshape the nation.
Since its supporters still don’t have the votes to pass the bill, it also amounted to the first and perhaps most crucial test of the idea that his “Art of the Deal” business approach can translate to politics.
Repeatedly on the campaign trail, Trump boasted that he makes “great deals” and lambasted the negotiating skills of his predecessor President Barack Obama — for instance over the Iran nuclear deal, as he argued he would have driven a much harder bargain.
“In negotiation, you must be willing to walk,” Trump said in a major foreign policy speech in April 2016.
“The Iran deal, like so many of our worst agreements, is the result of not being willing to leave the table.”
On Thursday night, Trump turned those tactics on his own side.
But the scale of his wager was clear when House Speaker Paul Ryan could not say whether the bill would pass or fail.
“We have been promising the American people that we will repeal and replace this broken law, and tomorrow we’re proceeding,” a terse Ryan told reporters.
Winning is easy, governing is harder
The high-stakes meeting of Republicans Thursday night, including dueling factions of Freedom Caucus conservatives and Tuesday Group moderates, followed days of intense political intrigue as the bill’s fate hung in the balance, and came after repeated changes to the legislation designed to win over holdouts.
This was not how the new Republican order was supposed to dawn. Instead of a united push towards a GOP holy grail, repealing Obamacare, the drama exposed a dangerous fault line in the party.
The desperate scramble for votes, conflicting signals, factional intra-party warfare, and the defiance shown by rank-and-file members to their leaders signaled that one-party rule may turn out to be just as complicated as life in a Congress where Democrats and Republicans share power.
But really, it shouldn’t have been this hard.
The idea of repealing Obamacare has galvanized the GOP for years, is demanded by the party’s raucous base and looked certain to be one of the easiest lifts for the new White House and its Republican majorities.
After all, the GOP voted more than 50 times to repeal Obamacare or parts of it — though always knew it would ultimately be thwarted by the Senate or Obama’s veto.
But Trump and Republicans are learning that votes cast by a governing party are tougher than those made in futile protest.
Until a vote occurs, Ryan is in a position familiar to his often infuriated predecessor John Boehner — who endured political and fiscal cliffs and running showdowns with the ultra conservative Freedom Caucus while he was speaker.
Boehner predicted last month that Republicans would never repeal Obamacare, but would end up fixing it — because they would “never ever agree what the bill should be.”
“Perfect always becomes the enemy of the good,” he said, prophetically.
Ryan’s difficulty in changing the equation that often frustrated Boehner suggests that his caucus remains as unsuited to governing as the one that eventually brought Boehner down.
Not everyone charmed by Trump
All day on Thursday, there came word of increasing frustration among party leaders on the Hill and the President’s associates in the White House at the malcontents of the ultra-right Freedom Caucus.
“It’s fairly amazing that even after meeting with President Trump, they are holding out for removing health care from people with preexisting conditions, something they know could never pass and goes against everything President Trump promised during the campaign,” one GOP aide told CNN’s Lauren Fox.
Freedom Caucus Chairman Mark Meadows diagnosed the problem: “We have not gotten enough of our members to get to yes at this point.”
The situation placed the political interests of Freedom Caucus members, who fear primary challenges from their right, and Tuesday Group members who fear the price to be paid if the bill ejects millions from health care rolls, against those of the new President.
It may be that repealing Obamacare will come back to haunt Trump in the long term. But for now, the President needs a political win to steady his administration, which is reeling from speculation about his campaign’s ties to Russia, the double failure of his travel ban and his own penchant for setting off self-defeating political controversies.
The high stakes for Trump were evident on Thursday night, when top aides including Chief of Staff Reince Priebus, Steve Bannon and Kellyanne Conway were spotted heading into the meetings with Republican lawmakers.
His budget director, former Rep. Mick Mulvaney, delivered the threat: Vote for the bill or be “stuck with Obamacare.”
Trump has hosted multiple meetings at the White House and blitzed lawmakers with charm and persuasion.
But every concession Ryan and Trump mooted to members of the most conservative faction, they risked ebbing support from moderates.
And it looked for hours on Thursday that the White House was oblivious to the ebbing support for the bill.
The tug-of-war between the factions angered some other Republicans who are not part of either faction and resent their influence, like Alabama Rep. Bradley Byrne.
But Byrne predicted that when the bill finally came to the floor, political reality would kick in.
“If you are a Republican you have one choice. You’re either going to vote with Donald Trump to repeal and replace Obamacare or you’re going to vote with Nancy Pelosi to defeat the only bill that will repeal and replace Obamacare. And if you’re a Republican, that’s a pretty simple choice.”