100% his plan the first time was to lose, talk a lot of shit and complain. Sell a bunch of merchandise and try it again over and over, grifting millions from idiots.

You can see it immediately when he wins. Both his and Melania’s expressions when they get the news show that winning wasn’t the plan. It’s also why he immediately started talking about fraud. He didn’t have any prepared talking points for winning, they were all based on losing and using that to power his next scams.