An honest question. How does Trump keep "winning" in the face of everything that was against?

The Dems have helped immeasurably. Hillary might have been the most hated candidate in my lifetime. NOW, they have candidates sounding off about the wonders of democratic socialism. 

Also, he is a narcissist (all Politicians?). They love to take a punch and counter. 

Widespread and deep corruption. DUH.

Trump marketed himself.   Surely you remember a marketing plot where millions of people were convinced to buy a pet rock.  The guy who thought of it laughed all the way to the bank, just like Donald Trump is doing.  But in Trump's case the money is our tax dollars, and, according to reports, huge sums of money from Russia, Saudi Arabia, Qatar, Turkey, Israel and whatever other country wants to buy influence.  He's not a political phenom.  He's a political criminal. If you have to support someone, support someone who"s honest and has good moral character.

He's had the truth on his side for starters. He's also accomplishing all of the things he campaigned on. He has great political instincts and a base that has stuck by him through it all.

Millions of Americans saw through the derangement and tomfoolery the U.S. political arena had become and Trump was one of them. 

How? Easy: the democrats’ hatred of him.

At this point, most people in the GOP are afraid of him

Really every time he beat democrats it was really because they fell flat on their faces from basic emotions or on their own deficiencies.

simple, he was chosen for this role by God Almighty