So, I just realized what seems to be happening.
It appears to be a "rope a dope" strategy. Trump is letting the press and Hillary pummel him, throwing whatever they can at him, and wearing themselves out while fracturing their credibility.
If the public is aware, even on a subconscious level, of media bias against Trump in August, by the time October hits, anything they attempt to "surprise" him with should be a glancing blow. The voters won't take it seriously.
The press have recontexualized, revised and even outright fabricated to make negative stories about Trump. Don Lemon and others like him are seen as untrustworthy. And Trump keeps taunting them each time they start to fatigue.
All those years of hanging out with boxing legends appears to be affecting Trump's campaign.