Part of Trump's "learning experience" was seeing how members of Congress may care more about what their constituents think than their president does. Trump may be the leader of the Republican Party, but he isn't its CEO.

Winning isn't everything, and the "little s***" matters

Trump likes to win. He told the country during the presidential campaign that we would all get so tired of winning under him that we would all be so bored. The Art of the Deal author hyped himself as the best dealmaker anyone's ever seen.

Instead, his first major effort at legislating handed him a stunning loss. It was a textbook chapter in how not to legislate.

Part of the problem is that Trump wanted a win on health care so badly that he may have been blinded by his willingness to take any win.

He outsourced the details to Ryan and others, and when it got difficult, Trump didn't have enough policy knowledge to close the deal.

"How he was dismissive of policy concerns, and instead focused on the big picture and big political issue, that is never going to get you a win when you're negotiating with Congress," Conant warned.

Health care affects one-sixth of the U.S. economy and includes lots of "little" things that are important to real people's lives.

Every year Medicaid expansion is limited or rolled back means potentially millions of people who don't have access to health care.

Every "essential health benefit" that's put on the chopping block, for, oh say, whether your insurance is required to cover emergency room visits, means potentially thousands of dollars in or out of constituents' and hospitals' pockets.

The "little" stuff is the important stuff.

Conservative writer Matt Lewis observed during the brief debate over the GOP health care bill how far it strayed from Trump's campaign platform. "He ran as a guy, 'I will solve your problems. I want to take care of everybody. Nobody's going to lose anything. Everybody's going to have the best health care.' This health care plan is off-brand for Donald Trump," Lewis told NPR's Mara Liasson.

An enduring problem for the president may be that his brand of populism doesn't necessarily match the small-government conservatism that defines the House GOP Conference.

Sure, Trump made the phone calls and lobbied wavering Republicans, but he grew impatient and frustrated. After less than three weeks, he issued an ultimatum to those hardline conservatives — he was done negotiating: vote for this bill, or Obamacare stays in place.

It was a big gamble, and he lost.

"Winning" isn't everything; it really is how you play the game in Washington that enables winning. And when it came to playing the legislative game, Trump's lack of attention to policy detail, impatience and cavalier impetuousness cost him.

"He should know, from being engaged in a lot of negotiations, if you're constantly looking over your shoulder and needing someone to fill in the details in the conversation sometimes that doesn't wear real well," the strategist said.

Learning from Obama

There's a reason it took former President Obama more than a year to pass the Affordable Care Act.

He knew the details, and was often the best — and only — salesperson for it. He took the show on the road and got into the nitty gritty.

Pete Souza, the former White House photographer, subtly made that point in a post on Instagram on Saturday:

"Give credit where it's due, Obama was really good at that," the strategist said. "Obama was really good at working with individual members knowing the legislation as well or better than they did. They [the Trump White House] need to get to that level, or close to it, or there are going to be gross inefficiencies built in and opportunities that are lost."

That is going to have to include more coalition-building inside and outside the GOP conference, with outside conservative groups, as well as industry groups.

"He didn't spend much time or political capital to get this bill through," Conant said.

Conant also pointed out that part of the problem is a level of distrust within the White House for everyone in "the establishment" and anyone who hasn't been on Team Trump all along.

"There continue to be a lot of vacancies," Conant said, "and they have rejected a lot of people who have government experience because of loyalty tests from the campaign."

That eliminates a lot of professionals with experience on Capitol Hill.

If Trump doesn't start to focus on the details and become more invested in how government works — something he has always been loath to do — he should expect similar results.

"There's an eagerness on all sides to move on, to put this episode behind and move on to a new issue," Conant said. "But regardless of what issue we turn to next, Trump will likely run into the same internal GOP divisions and partisan opposition. To be a successful president, Trump will have to display skills that we have not yet seen from him.

"It will require humility, patience, outreach to opponents and the forging of consensus."

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