No, but only because Trump didn’t need to make himself appear weak: Hillary’s allies in the media did that for him. And for all those that think Trump isn’t aware of The Art of War, please do your research. Just read his work. He actually lists it in Trump 101.
Sun Tzu taught that all competition is a comparison. The nature of the comparison depends on the “rules of the ground”, that is, the big picture in which the comparison is made. In running for president, there are two comparisons: the one that wins the nomination and the one that wins the elections.
In the first comparison, comparing Trump to more established Republican candidates, the media worked for Trump, thinking that “established” meant stronger in opposing Hillary. As 90% Democratic, the media naturally hated established Republicans and acted on their feelings. This is never “strategic” but nowhere is the misunderstanding of the nature of strategic competition more pathological than in the modern media. A practical understanding of strategic strength was much more prevalent in the media during WWII than it is today. Did Trump expect this media support? Perhaps, but he certainly knew how to capitalize on it to win the nomination.
In the second comparison, between Hillary and Trump, the media again refused to look at the rules of the battleground. Winning the presidency is not a popularity contest where you can run up the score in California and NY. You have to win states. Here, again, the media did Trump’s job for him. Assuring Hillary, themselves, and the rest of the world that the “blue wall” assured Hillary of winning states like Michigan. The “pundits” are making exactly the same mistake today in declaring which Democratic seats are “safe”.
Trump’s genius is in ignoring the “common knowledge” going after the states that were part of the “blue wall”. You can see him doing the exact same thing now (if you open your eyes) going after those “safe” congressional seats that assure the Democrats of a blue way. Trump did and is actually forcing the comparison everywhere rather than assuming where and how it doesn’t matter. Trump has defined a new ground for comparison, “putting America first”. This is Sun Tzu’s idea of finding ground that no one has yet occupied. We cannot know how comparisons on this ground play out based upon traditional party voting patterns. They are new. However, Trump has been successful in the past at playing this exact comparison.