There is a huge amount of stigma around homelessness and poverty. "Those people are irresponsible and they deserve everything that happens". His story just reminds us that what happened to him can happen to most people.
There is plenty of collateral damage when technology disrupts markets and jobs appear and disappear. But being possessing a stale skill set with no plan (or willingness) to retrain is simply irresponsible.
If you've sent out 800 resumes for a type of position and haven't gotten so much as a callback, you are in denial.
Absolutely, it can happen to anyone, whether you're a "good citizen" or not.
Without more details of his situation I can't say if I think he was being irresponsible or not, but irresponsibility (which is common) should not cause homelessness (which is bad).