U.S. Speaker of the House Paul Ryan walks with OMB Director Mick Mulvaney to a meeting of the House Republican caucus at the U.S. Capitol March 23, 2017 in Washington, DC.
Win McNamee/Getty Images
U.S. Speaker of the House Paul Ryan walks with OMB Director Mick Mulvaney to a meeting of the House Republican caucus at the U.S. Capitol March 23, 2017 in Washington, DC.
Now playing
02:08
GOP remains split on health care bill
CNN
Now playing
00:50
Tom Price: Individuals will not lose coverage
Ohio Gov. John Kasich ISO for State of the Union.
CNN
Ohio Gov. John Kasich ISO for State of the Union.
Now playing
00:54
Kasich: 'Unless it gets fixed, I'm against it'
Tom Price sotu 6/25
CNN
Tom Price sotu 6/25
Now playing
02:39
Price won't say if health bill cuts his taxes
Fox News Exclusive
Now playing
01:15
Trump admits he called GOP health bill 'mean'
Senate TV
Now playing
01:24
Senator: GOP making decisions 'in a back room'
trump cbs
"Face the Nation"/CBS
trump cbs
Now playing
02:32
Trump: GOP plan covers pre-existing conditions
US President Donald Trump delivers a statement on Syria from the Mar-a-Lago estate in West Palm Beach, Florida, on April 6, 2017.
Trump ordered a massive military strike against a Syria Thursday in retaliation for a chemical weapons attack they blame on President Bashar al-Assad. A US official said 59 precision guided missiles hit Shayrat Airfield in Syria, where Washington believes Tuesday's deadly attack was launched.
 / AFP PHOTO / JIM WATSON        (Photo credit should read JIM WATSON/AFP/Getty Images)
JIM WATSON/AFP/AFP/Getty Images
US President Donald Trump delivers a statement on Syria from the Mar-a-Lago estate in West Palm Beach, Florida, on April 6, 2017. Trump ordered a massive military strike against a Syria Thursday in retaliation for a chemical weapons attack they blame on President Bashar al-Assad. A US official said 59 precision guided missiles hit Shayrat Airfield in Syria, where Washington believes Tuesday's deadly attack was launched. / AFP PHOTO / JIM WATSON (Photo credit should read JIM WATSON/AFP/Getty Images)
Now playing
01:32
Trump: 'No particular rush' on health care
Donald Trump
CNN
Donald Trump
Now playing
01:14
President Trump guarantees health care deal
Now playing
01:35
GOP congressman: Greater risk, greater premium
Paul Ryan
CNN
Paul Ryan
Now playing
02:39
Race for health care votes is on, again
TRUMP VOTERS
CNN
TRUMP VOTERS
Now playing
02:47
Health care failure won't deter Trump voters
Republican Congressman Charlie Dent speaks during an interview at his campaign office in  Allentown, Pennsylvania on November 2, 2016.
EDUARDO MUNOZ ALVAREZ/AFP/Getty Images
Republican Congressman Charlie Dent speaks during an interview at his campaign office in Allentown, Pennsylvania on November 2, 2016.
Now playing
01:21
GOP Rep.: Health law failure on Freedom Caucus
Kasich pathetic health care bill bipartisanship sotu_00000000.jpg
CNN
Kasich pathetic health care bill bipartisanship sotu_00000000.jpg
Now playing
01:47
Kasich: GOP, Dems not working together is pathetic
Senator Bernard Sanders asks questions to Betsy DeVos during her confirmation hearing for Secretary of Education before the Senate Health, Education, Labor, and Pensions Committee on Capitol Hill January 17, 2017 in Washington, DC.
Brendan Smialowski/AFP/Getty Images
Senator Bernard Sanders asks questions to Betsy DeVos during her confirmation hearing for Secretary of Education before the Senate Health, Education, Labor, and Pensions Committee on Capitol Hill January 17, 2017 in Washington, DC.
Now playing
00:55
Sanders urges Trump to join him on drug bill
Paul Ryan health care bill presser_00000000.jpg
Paul Ryan health care bill presser_00000000.jpg
Now playing
01:32
Ryan: This is a disappointing day for us
CNN
Now playing
01:21
Ryan: Obamacare is the law of the land
WASHINGTON, DC - MARCH 09: Australian Prime Minister Julia Gillard addresses a joint meeting of the U.S. Congress from the floor of the House of Representatives at the U.S. Capitol March 9, 2011 in Washington, DC. Gillard emphasized the long and strong bond between her country and the United States. (Photo by Chip Somodevilla/Getty Images)
Chip Somodevilla/Getty Images/File
WASHINGTON, DC - MARCH 09: Australian Prime Minister Julia Gillard addresses a joint meeting of the U.S. Congress from the floor of the House of Representatives at the U.S. Capitol March 9, 2011 in Washington, DC. Gillard emphasized the long and strong bond between her country and the United States. (Photo by Chip Somodevilla/Getty Images)
Now playing
01:38
House Republicans pull health care bill
John Lewis health care bill speech sot_00001310.jpg
John Lewis health care bill speech sot_00001310.jpg
Now playing
02:28
Rep. Lewis' passionate speech against GOP bill
WASHINGTON, DC - MARCH 21:  U.S. President Donald Trump speaks during a bill signing ceremony in the Oval Office of the White House March 21, 2017 in Washington, DC. President Trump has signed S.442 - National Aeronautics and Space Administration Transition Authorization Act of 2017 into law.  (Photo by Alex Wong/Getty Images)
Alex Wong/Getty Images
WASHINGTON, DC - MARCH 21: U.S. President Donald Trump speaks during a bill signing ceremony in the Oval Office of the White House March 21, 2017 in Washington, DC. President Trump has signed S.442 - National Aeronautics and Space Administration Transition Authorization Act of 2017 into law. (Photo by Alex Wong/Getty Images)
Now playing
00:26
White House on health care bill: 'This is it'

Story highlights

After days of trying to charm members of Congress, Trump gives an ultimatum

Trump's bet represents the most audacious risk yet of his presidency

(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 win 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.

With the result of Friday’s vote uncertain, there were already signs that the White House was preparing to lay the blame on House Speaker Paul Ryan should the bill fail.

Trump is “pissed” that the bill is struggling to pass, a source told CNN. The President is also frustrated that his staff has been unable to clear the way to passage and feels misled by those aides who advised him to sign onto the GOP leadership’s repeal bill, the source close to the President said. Trump realizes his credibility will take a hit if the bill goes down.

Another source told CNN that the White House is unhappy with the way Ryan has handled the repeal effort. Ryan’s staff responded by issuing a long list of media appearances and advocacy for the bill by the speaker, and said he and Trump spoke for 45 minutes by phone on Thursday night.

01:45 - Source: CNN
Rep. Massie slams GOP House leadership

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 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 many 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.

02:31 - Source: CNN
Freedom Caucus member still a 'no' on GOP bill

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.”

CNN’s Lauren Fox, Deidre Walsh, Jeremy Diamond, Phil Mattingly, Jeff Zeleny and Dana Bash contributed to this story