According to the last Star article, "Captain John" owns a small apartment building in Scarborough. I don't know which property, or what that might be worth, but couldn't the city and other creditors go to court to force back payments, or even possession of that property? I don't want the guy to become homeless or anything, I figure that a Scarborough low-rise should be worth well over $1,000,000 which should more than cover his outstanding debts and leave some money to live on, enough even to buy a condo to live out the rest of his life. Right now, he's holding on and accumulating even more debts.
I'm a compassionate person, but if TCHC is busy evicting desititute seniors and throwing them on the street (a serious problem), by the same token the city should be going after "Captain John" regardless of what he did 25-30 years ago (which won't end up throwing him on the street).