After an unsuccessful attempt to work with House Republican leaders to repeal Obamacare, President Trump is now widely expected to pursue Democratic votes on other priorities, a decision that carries its own risks of failure and possible increased tensions within the party he is trying to lead.
Since the ill-fated American Health Care Act was pulled from consideration Friday, Trump's spokesmen have talked more about working with Democrats. The president himself has alternated between blaming Democrats for the problems with Obamacare and enlisting their help in fixing them.
"Yes, I think the president will push for an agenda that is more in line with what he hopes to accomplish — initiatives like tax reform and infrastructure investment," said Michael DuHaime, a Republican strategist. "He will be more invested in the outcome and can therefore spend more time using his political capital with GOP voters to unify the disparate factions of the party and sway members of Congress."
"And there is a shot some Democrats will vote for an infrastructure bill, meaning the chance to tout a major bipartisan accomplishment," he added.
"At the Republican convention, you saw all these lobbyists saying, 'Trump will be OK because he will sign all our bills,'" said Mickey Kaus, a liberal blogger who supports the president on immigration. "And [House Speaker] Paul Ryan can't even get his own bill passed."
FiveThirtyEight's Nate Silver argued that Trump was elected to fulfill a different mandate than Ryan.
"The public may have wanted change when they elected Trump, but this was not the sort of change they were looking for," wrote Silver. He observed that Trump "tends more toward the center than either the Ryan or the Freedom Caucus wings of the GOP."
Despite sniping from some Trump allies, there was little public distance between the president and Ryan during the healthcare fight. Trump worked until the final hours to win over recalcitrant members of the conservative House Freedom Caucus.
But Trump also gave every indication he was more interested in tax reform than Obamacare. After leaving many conservatives with the impression he was more willing to negotiate on the details of the healthcare bill than Ryan was, his closing argument to highly ideological and policy-oriented lawmakers was based almost entirely on political considerations.
That move didn't jeopardize his relationship with Republicans — at least not yet.
"As long as Reince [Priebus] is chief of staff, he is going to encourage a good relationship with Ryan and the congressional leadership," said Republican strategist Jim Dornan, who thought it might have been a learning experience for the president in dealing with Capitol Hill conservatives.
However, Trump was clearly outflanked on the right by about 40 Republicans who balked at the plan he supported, likely forcing the president to rethink his approach next time.
"Reagan found himself in a similar position," said historian Craig Shirley, author of Reagan Rising: The Decisive Years, 1976-1980, pointing to a 1982 deal with the Democrats to raise some taxes. "He was on the opposite side of the House conservatives — Jack Kemp, Newt Gingrich, Bob Walker — and they beat him in the first round. He had gone along with the establishment."
"Trump found himself on the wrong side like Reagan did," Shirley continued. "All of the sudden he was on the side of the establishment instead of being true to his campaign pledge."
Trump campaigned more as a consummate dealmaker and practical businessman than as the most committed movement conservative. Democratic strategist Rodell Mollineau, a former Harry Reid adviser and veteran of the fight to pass Obamacare over seven years ago, said the healthcare fight undercut the argument that "being ideologically flexible would make Trump a better president."
"When your only driving motive is to have a deal, and you don't have any dog in the fight as to what that deal looks like [you are] heading for trouble," he said. "Ryan has always been upfront about where he is coming from and it doesn't [mesh] with where Trump is coming from, his populist pitch."
"Trump isn't a hardcore ideological conservative, but the party he represents is," said Dornan.
But it may be difficult for Trump to find a winning combination that includes Democrats. First, there aren't as many centrist Democrats as there were even when Obamacare was originally passed, in part because Republicans unseated many of them.
Trump's low approval ratings and recent setbacks have also energized Democrats to oppose him rather than make deals. That means winning over Democrats at this point might require presenting "a center-left bill," Mollineau said, and that carries its own risks.
"If he goes that far to the left, he loses most of the Republican Party," he added. "You can't lose most of your party on a major piece of legislation."
Nor would Trump be guaranteed of picking up enough Democratic votes. "We are big boys and girls, but he has done nothing but antagonize Democrats," said Mollineau. "A lot of Democrats think the president is a liar," and would not trust him even if he offered a compromise.
"I just don't think the Democratic base is going to allow their members to vote with him, except maybe on infrastructure which isn't that partisan an issue," Dornan concurred.
But some say it's possible, and Kaus advised Bill Clinton-style triangulation. "He needs to be somewhere between Paul Ryan and the center of the Democratic Party," he said. Trump has already adopted a position on Social Security and Medicare closer to Clinton's 1996 campaign platform than Ryan's views.
That idea could just mean a subtle shift in focus for Trump as he tries to collect votes.
"Why are we trying to placate a bunch of guys in safe Republican seats when there are bunch of guys like me in D plus 2 seats who are much more exposed?" Dornan said, outlining the GOP moderates' argument.
Trump isn't an easy ideological fit for either party. His policy views are vague and he lacks institutions to help fill them out. So he has to rely on preexisting conservative think tanks that may not be a perfect fit.
"Reaganism was a distinct separate part of conservatism for a long time before he became president," Shirley said. "Trumpism is a new phenomenon and without details or institutional support it's hard to coalesce around it."
"Next time things will be done much differently, much more efficiently, much more geared toward winning, not speed," Dornan said. "All hell breaks loose if the far right opposes Trump's tax reform bill. Trump is going to say: I'm in charge here."
"As a Republican," he added, "I am not looking forward to seeing that."