In light of the current debate over health-care reform, few points about "winning": In the Beltway, there tends to be an assumption that a president "wins" when he gets Congress to pass the legislation he supports. Than can be a victory, but that "win" can sow the seeds for a greater defeat later.
For instance, President Obama "won" by getting Congress to pass the ACA on a party-line vote. It was a substantial legislative achievement, and components of it could very well have a long legacy. But the ACA's passage also crippled the rest of the Obama administration's agenda and contributed to the evisceration of the Democratic party's bench. Maybe that trade was worth it, but it exacted a high long-term political price, too.
The experience of the Obama administration might prompt the Trump White House to think about what its real policy priorities are and how it can advance those priorities without endangering a critical mass of public support.