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I think he's much too fragile of ego to intentionally lose. I doubt he even let his kids win at games as children.
Partly because I doubt he ever actually played with them but also because he's a complete cunt.
Had he lost in 2016, I think he would have been secretly happy about it, but would have publicly griped about "stolen elections" and the like. Then, he would have gotten paid to go on talk shows and give speeches for 4 years about how the Democrats stole the election from him and how he could easily fix every problem facing America (without actually giving a single detail on what he'd do).
I just don't feel that lines up with his behaviour anywhere else.
He has a pathological need to be seen as "best at everything" and will publicly say embarrassing, easily exposed lies.
He claimed he had the biggest inauguration. He claimed to be in incredible physical and mental health. He claimed the head of the boy scouts called to tell him "he gave the greatest speech they'd ever been given".
He took a sharpie to a hurricane map because he knows better than meteorologists. He told people to inject bleach because he knows better than experts in medical science. Butch manly men walk up to him crying tears of gratitude because they love him so much.
The "stolen election" excuse is another of these excuses. He can't admit he lost because only losers lose, so he started a lie that blamed anything except his personal failings.
Im sure he played plenty of games with Ivanka, all of them he learned from prostitutes.