I wouldn't classify someone who has had six bankruptcies as a "winner". One, maybe two I can understand. But six, that's just poor business management and a great example as to why we're heading into a Trump-powered recession.
He's a billionaire real estate magnate, who had a very successful television show, and became the President of the United States despite extreme opposition from both major parties and the media.
It's obvious from your other comments that you viscerally hate this man, it might good for you to see things with a bit more objectivity.
Unfortunately the Russian interference in the US elections & 5 of the campaign officials convicted of various election-related crimes doesn't make it look like the President had a competent, ethical and legal campaign.
https://www.thoughtco.com/donald-trump-business-bankruptcies...