Go back and look at his history, even before he got into politics.
He has always had exactly one tactic. Use his near-infinite resources to delay things indefinitely until the other side either gives into his demands or simply runs out of resources to keep fighting. Of everything he has ever been involved in, I don’t think he’s ever actually won a single thing on the merits. And when that doesn’t work?
He caves. He always caves. His opponents walk away with everything they want while he gets nothing, and then still goes out to the press and tells everybody what a shrewd negotiator he is. The same thing happens every time he sits on the other side of a negotiating table and couldn’t either bully or delay his way out of it. His entire negotiating skillset is to hide behind an army of lawyers until the other side runs out of money. He banks on the fact that very, very few people (or even businesses for that matter) have the resources needed to outlast him and force him to the negotiating table in the first place, because he has no clue what to do when he gets there.
The man is pathetically stupid to a point I did not think was achievable by human beings. Give me an hour, a deck of cards, and a poker table with him and I’d be able to own everything that man has, and I’d be able to do it with nothing more than a jack of diamonds and a Forest card from Magic: The Gathering. He was just born on top of a pile of money that most human beings couldn’t burn through even if they tried, and Trump took that as a personal challenge.