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Donald Trump certainly ran an unconventional campaign, but Trump always plays to win. Winning is his obsession. He made use of his skills as an entertainer manipulating the media and consuming air time for "free". He also understood that Americans are very ignorant and vote their emotions. He simply told each audience exactly what they wanted to hear, and they were gullible enough to believe him. The rust belt factory workers and the Appalachian coal miners bought his swan song.
He does play to win, but what was the BEST win for him in this case?
I remain convinced his real motivation for running for president was self-promotion of himself and the trump brand using, as you suggest, free media coverage. And it truly is a brilliant marketing tragedy. This allowed trump to say anything and everything he wanted.
For him, the BIG win was to lose the election, but continue on as quasi public mouthpiece of the new republican party\revolt. If he had lost, his brand would have been even bigger and more popular around the world, and untainted by any further political scrutiny. He would keep himself in the public eye with claims that HC rigged the election. Trump likely would continue to hold rallies in trump friendly locations. At his rallies and in the media he could lie as often and much as he wanted because as a former candidate the FBI would not be investigating him and the media would not be doing any significant fact checking. President Clinton would have pursed investing the russians, but far less focused on trump's ties with the russians, and she clearly would not have wanted to be viewed as persecuting her political opponent after the election.
I have no doubt trump did everything he could to win the election, but deep down he didn't want to really win, and didn't expect to win. If he could have scripted the outcome of the election, he would won the popular vote, but lost the electoral college, thus claim he was the TRUE winner, and the REAL elected President by total votes, and then proceed he was cheated out of it by a rigged system control by Crooked President Hillary Clinton. That would have been his perfect outcome (BS story), an outcome that the Republican party could rally around for 4 years and beyond. ie: "Trump won the national vote, but HC and the russians cost him the electoral college" would be the Republican outcry.
He wanted to be seen as Rocky in the first movie, a long shot that was would have won if the bell had not rung to end the fight.
Here is a caption for a cartoon. Trump: "The election was rigged, I won the popular vote, but HC won the Electoral College. The bitch cheated and made me president".