Instead, its initial failure rattled the new President in his first days in office, giving him a rude awakening on everything that is frustrating about Washington.

Despite the latest flurry of activity on the Hill Wednesday night , Trump's campaign promise to gut his predecessor's landmark health care law looks certain to remain unfulfilled anytime soon. But it won't be for a lack of trying.

Even as late as Thursday morning, House Republicans were trying to make progress bridging an internal party divide between conservatives and moderates, releasing legislative language on an amendment in hopes of having a last-minute vote before the 100-day deadline Saturday.

From the beginning of Trump's term, the President, together with House Speaker Paul Ryan, was quick to make health care overhaul his most urgent legislative priority of 2017, staking an enormous amount of political capital on a goal that has rallied and united Republicans for nearly a decade. But rather than notching an early win, Trump instead suffered an embarrassing defeat when the Republican health care bill was yanked from the House floor last month.

The votes simply weren't there.

But the flurry discussions leading up to that dramatic moment gave Trump an invaluable crash course in governing. Perhaps the biggest takeaway: legislating with a fractured GOP requires political agility and policy sophistication -- and more than just a willingness to negotiate.

For now, Trump's allies are downplaying the significance of his failure so far to repeal Obamacare. Former House Speaker Newt Gingrich, an informal adviser to the President , went as far as to call the failure a blessing in disguise -- a "minor glitch compared to everything that could have gone wrong."

"I actually think it is very good for the long-run health of the administration that they're learning early that managing the Congress is a very difficult and very complicated job," Gingrich told CNN. "If they'd been able to rush it through, they wouldn't heave learned just how hard everything in Congress is."

And in the final hours leading up to the symbolic 100-day mark for Trump, Republican lawmakers were still trying score a deal.

Members of the conservative House Freedom Caucus, a group that had stubbornly opposed the first GOP House bill to overhaul Obamacare, announced on Wednesday that it was now backing the legislation. That course correction came after the group's chairman, Mark Meadows, and Tuesday Group leader Tom MacArthur negotiated an amendment that would let states apply for waivers that could gut several core Obamacare insurance reforms, including those that protect consumers with pre-existing conditions.

With the Freedom Caucus now on board, the pressure is now on moderate Republicans.

"I think anybody who is wavering feels some pressure because the vast majority of our conference wants to pass this bill," MacArthur, the New Jersey Republican and the author of the latest amendment, told reporters Wednesday.

They face a tough political choice: Vote for an unpopular bill that experts say would hurt people with pre-existing conditions, or buck their own president and risk getting blamed for refusing to help their party repeal Obamacare.

"I spent the whole work period hearing from people pissed about pre-existing conditions," one moderate lawmaker told CNN on Wednesday. "This isn't helpful."

Political divide

Trump still needs to find consensus between two long-opposed factions of his party if he wants a shot at overhauling Obamacare. Two factions that -- after a rough start to the conference have only lost trust with one another, not built it.

The differences between moderates and conservatives aren't new -- those disagreements have threatened to derail a host of Republican priorities before -- but the campaign to repeal Obamacare has only sharpened those divisions. So far, it is the GOP conference's shortcomings that have blocked Trump's pursuit of a major legislative accomplishment.

The plan to repeal the Affordable Care Act had always been to use a process known as a budget reconciliation bill, which only requires a simple majority in the Senate. But the effect was that it automatically ostracized Democrats from working with the President on reforms to Obamacare. To accomplish anything that resembles wholesale repeal of the law, Trump would need the full force of his party behind him.

What is not clear is whether Trump can ever overcome the two very different visions within the GOP of what the government's role in health care should be.

Many moderates have long advocated that while the Republican Party has been running to repeal Obamacare for the last seven years, they also have been promising constituents back home to keep in place popular provisions like protections for people with pre-existing conditions. Many moderates also railed against any proposal to repeal Medicaid expansion that had benefited their constituents.

Meanwhile, conservatives, including the Freedom Caucus, wanted the GOP's health care repeal to gut more of Obamacare's insurance provisions, specifically those that require carriers to provide comprehensive coverage and to charge the same premiums to consumers regardless of their health status.

"You are probably all familiar with that little term 'repeal and replace' ultimately that's the promise we made and some of us wanted to do that as much as we possibly could," Rep. Trent Franks, an Arizona Republican and House Freedom Caucus member said.

Conservative members were looking for a quick and complete repeal, similar to a 2015 legislation that passed both houses before being vetoed by President Barack Obama.

When House leadership unveiled a bill with refundable tax credits to help people pay for their premiums, some conservatives rushed to dismiss the package as little more than "Obamacare lite."

I commend @freedomcaucus for staying united against Obamacare Lite. Enough NO votes to stop bill and restart negotiations w/ conservatives — Senator Rand Paul (@RandPaul) March 22, 2017

The crux of Trump's problem from the beginning has been a simple math problem. Trying to please the conservative Freedom Caucus only alienated moderates. Trying to assuage moderates' concerns only alienated the Freedom Caucus.

Ultimately, the Republicans' inability to bridge their ideological divides led to the bill's collapse in late March. And Trump -- despite his bluster -- still hasn't overcome that.

"I don't think they've been close. I don't know how with Republican votes they are going to bridge that gap over there. I think it has been wishful thinking, and the President is overstating, or overestimating his leverage. When the Freedom Caucus, when those folks aren't afraid of him or primaries ... when his approval ratings is in the 30s, it's a problem," one Republican senator said.

JUST WATCHED WH leads talks to revive Obamacare replacement Replay More Videos ... MUST WATCH WH leads talks to revive Obamacare replacement 03:46

Raising the stakes

Trump's initial struggle with health care has already set important precedent for the rest of his term in office.

The deep philosophical divide exposed over the first House bill has raised serious questions about the GOP's ability to tackle other ambitious legislative items.

"The failure to repeal and replace Obamacare in the House -- which was more the fault of House Republicans than the President -- is the most obvious stumble in President Trump's first 100 days," said Ari Fleischer, who was press secretary to George W. Bush in the beginning of the Bush presidency. "Every Republican from Trump on down promised to make it happen and it didn't happen. If they don't get it done, what the advantage of GOP control?"

The health care debacle has also left a mark on the White House's relationship with the House speaker and his aides.

While the two sides have insisted that they have a smooth working relationship, tensions are simmering. And there are signs that the White House is willing to play a more aggressive role in future legislative battles.

The most recent attempt to revive the health care bill by winning over Freedom Caucus members came largely at the insistence of the White House. While House leadership has been informed of ongoing discussions, it has not played a leading role in the renewed negotiations over the past few weeks.

And if the House ultimately takes a vote on the health care bill with the MacArthur amendment -- despite the grave reservations from moderates -- that would send a clear signal about the White House's political orientation, while empowering the conservative wing of the House.

GOP Rep. Charlie Dent, a leader of the Tuesday Group, bristled at the latest turn of events on Wednesday, dismissing it as nothing more than "an exercise in blame shifting."