4) Start with giveaways, then move to harder stuff. The GOP Obamacare proposal was a bill that would have cut the federal deficit in part by reducing the number of Americans with health coverage. That’s not exactly a recipe for popularity. Had Trump and the House GOP tackled, say, an infrastructure bill first, the story from Capitol Hill would have been a president and Congress giving things to the American people — surely a more popular legislative start to an already controversial presidency.
5) ‘The Art of the Deal’ doesn’t work with ideologically-driven politicians. The pundits mentioned Trump’s most famous book thousands of times during the Obamacare negotiations. But in dealing with the doctrinaire conservatives in the House Freedom Caucus, Trump was facing differently-motivated partners than in the deal-making recounted in his 1987 book. If the president wants to succeed in Washington, he’ll have to learn how to deal with people who aren’t in it just for the money.
6) Nancy Pelosi was right. The former Speaker and current House Minority Leader said Trump made a “rookie’s error” in bringing the Obamacare measure to a finale too quickly. Before that, Washington insiders snickered when the president said in late February that “Nobody knew healthcare could be so complicated.” Of course, everybody knew it was complicated. After all, in 2009-2010 it took Democrats more than a year to pass Obamacare, and they had a huge majority in the House and a filibuster-proof majority in the Senate. Trump, the newcomer to Washington, thought it could be done quickly with less firepower on Capitol Hill.