Without a doubt it would require multiple successes. I happen to be of the opinion it can happen, it comes down to the will of his administration and the focus in knowing that what you are doing is right for the country. Let's all admit, if anyone can pull this off Trump has to be on the list, he proved that through the primaries and general election. The guy clearly knows how to win. Here is how I believe it can be done, much of it was spoken by Trump during the campaign:
1. Decrease costs- this means a lean and mean government. Getting rid of government waste, pet projects, unnecessary boondoggles and fluff. Looking at entitlements that are neither sustainable nor required for the health and well being of the nation. Dealing with illegal immigration in the form of a wall could save the nation over a hundred billion dollars a year according to some estimates. It's a no brainer, and would pay for the $1 trillion within a decade. We are seeing his eye for savings in his dealings with Boeing, and he isn't in office yet.
2. Renegotiating existing agreements- be they trade agreements, even borrowing agreements with nations who have exploited America (I believe even negotiations with creditors can be done). We are seeing these intentions with some of the appointments he has made on the trade file. He will confront China and the massive $800B trade deficit with them. He has fired a shot across the bow to a nation that has been taking advantage of America for a long time, this in itself is a big step. He isn't even in office yet.
3. Creating an environment that attracts businesses- in the form of lower taxes, lower regulation (which often cost a tonne to administer). This includes recovering the couple of trillion in foreign currency held by American corporations who will now be empowered to bring it back (and pay a one time tax $$$). More investment in American, more businesses= more taxes from the businesses, more tax revenue from the workers salaries and in the marketplace when they spend. We have seen this done in a small way with Carrier, this is a drop in the bucket, and he isn't in office yet.
I could get very specific, but you get the idea. Hell, I would love to work with an administration like he is putting together because he is developing a group that has ideas. I am finding from following Trump that he is not just about negotiations, he is about ideas. Building a better mousetrap. He likes to solve problems, and he gets the best who have solved many problems in the past. All he has to do is execute these ideas because many of them are common sense (something lacking in Canada I assure you). He is a typical successful businessman with an MBA background. Old school, if you will.
For the record, the Will of his team is what will matter. They will receive constant pushback, people from all sides trying to protect their "turf". For some of these people, it's not about what good for America, it's what is good for themselves. This has to be put to an end, America has $20 trillion to deal with and a very uncertain world. The world needs a strong America, take my word for it.