My father would qualify.
When I was growing up, he had his own business, and was very financially savvy. He taught me about investing, mutual funds, and retirement accounts when I was a teenager. He was maxing out his SEP-IRA every year. He built a custom house on an acreage mortgage free. He was on track to retire early.
And then the recession hit, and his business withered. And for whatever reason, he and my stepmom couldn't alter their lifestyle, even though relatively small changes would have been enough. He had paid for private college for the oldest stepchild when business was good. When the business starting failing, he couldn't cashflow the other kids, so mortgaged his house and took out parent plus loans in order to put the next 3 kids through private college, rather than apologize for the changed circumstances and make them take out their own loans, or change colleges.
Then the business ended completely. He had to sell his dream house to pay off the mortgage. He started living on his retirement accounts, paying fees in order to access them early. They moved across the country in order to help a family member in need, where they rented a large house for an ungodly monthly rent. (It had to be large enough for 6 kids, even though 5 were through college and out of the house, because of course they'll all come for Christmas and need their own room) Of course, neither could find jobs in the small town they moved to. So 2 years of no income, and large expenses, burned through a large portion of his retirement accounts.
They finally moved back to a large city, where they were both able to find intermittent work, that never paid enough. Of course, they still had to rent large houses in nice neighborhoods. They supplemented by raiding the retirement accounts.
Where are they now? All retirement funds are gone. He is 67 and still working, but starting to feel his age. They still have the parent-plus loans, with no hope of ever paying them off. Despite both working full-time jobs, they couldn't cover their expenses, and got behind on multiple bills (did I mention the large, lake-front house they rent?). He took social security in order to make ends meet. So when the day comes that he is physically no longer capable of working (and his job is a physical one), they will be well and truly screwed.
It's interesting because my mom is also in a bad place financially, has relied on family to support her for the last 5 years, and will need family (aka me) to support her for the rest of her life, and yet my father's situation seems so much worse to me. I think it's because my mom has always been bad with money, so I expected it. But my father was good with money, and still managed to screw everything up.