It wasn’t personal bankruptcy, but the bankruptcy of failed companies. Having four companies fail sounds like a terrible business record. Considering every real estate property is probably its own company (to allow external investments and protect the owners should that particular property fail), that depends on how many properties he has in total. Compared to that number, four failures aren’t a such an unbroken record of failure as they appear.
To be clear, I am not saying that Donald Trump would make a good president. He has a track record of great salesmanship, but that isn’t necessarily an important job qualification. I am, however, saying that this meme, while true, is misleading.
h/t Peter Shalen for the logic hole here.