So, how'd he do?
Donald Trump won tonight – because he lives to campaign another day. Strengths
Strong use of "Make America Great Again" literally and substantively throughout the night.
Great one liner when Clinton said she'd hate to live in a country where Trump was president "Because, you'd be in jail."
Hillary's all talk – no action.
Attacks on the moderator work for him – baiting the moderators into sounding like they're attacking him, whether true or not. Paints the media as part of the establishment, if not the Democratic Party opposition.
His body language while resting was strong. He wandered the stage, looking like a confident CEO listening to a board director arguing against him: bemused, confident, somewhat smug, arrogant. Some won't like that. But, it compared extremely well to Clinton's body language which was tense, angry, knowing she had everything to lose.
When he said "Her heart is filled with hate" the average viewer would agree, looking at Clinton's resting face which was most often angry, boiling mad, vitriolic and radiating hatred.
His answer to the question about whether he'd avoided taxes by declaring a $900 million loss was brilliant. Yes and here's why and so do her donors. Pitch perfect.
Likewise, when asked what he'd change about the tax laws, his answer was brilliant. "I'd change the carried interest provision which I use.... so do Clinton's donors... etc." Well played sir.
His answer to the "locker room" tape question was perfect. Not proud of it, then pivoted to hardly the biggest issue we're faced with.
He said he disagreed with his VP running-mate Mike Pence on policy toward Syria. The conventional political analysis will hold that this is a disastrous thing to say. But, Trump is not running a conventional political campaign. He's campaigning against convention. It was an honest answer. Average people will appreciate that.
When asked to compliment Clinton, he actually did. She did not do the same to him, giving a typically political response that was a false compliment followed by a pivot to her closing message.
Weaknesses
Didn't use "that's what you get with the same old, same old establishment" – instead he chose to attack Clinton in a similar vein: "you could have done something about it when you were a Senator... she's all talk, no action." That's effective, but it's too easy to shrug it off as a personal attack.
He would do much better without frequently interrupting her when speaking. It looks offensive, inconsiderate and rude – especially to a woman, a fire he doesn't need to stoke.
He needs to learn to let irrelevant attacks slide. He'd often have been better served by letting the debate move forward to the next topic, rather than by holding the spotlight on negative issues.
Threat to have a special prosecutor to investigate Hillary Clinton if he's elected president was unnecessary and just made him look like a bully.
The Bottom Line
This was a win for Trump because he had everything to lose. It's a low bar. The big question, though, is whether he can manage to stay on his message for the next month. He doesn't have the team he needs to capitalize on this performance and it's likely the media will paint it as a loss. That's going to hurt him with the average voter who doesn't watch debates, but is influenced third or fourth hand by media reports and water cooler talk.