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Diabetes in a cat is really rough too - my neighbor had to manage a cat that had diabetes, and she'd have to come home at lunch to give him shots, etc. I think it was a cat she rescued rather than one that she allowed to get heavy.
I am constantly fighting to keep the weight off one of my cats (Moose, appropriately enough). We feed our cats separately at specific times of day, with measured amounts.
Now that we've moved to a place that has two flights of stair indoors, I'm hoping that helps him too. We get him to the point where he's close to target, and then something always seems to happen to let it get back on him (switching diets due to crystals in his urine, etc). He seems to always be about a pound or two overweight, which is a lot of weight for a cat!
My grandmother allowed her cat to get like that. She fed it a diet of crab meat and cream for its entire short life. It was a nasty cat, and would scratch her when it was hungry. My father and uncles eventually took it away from her just before Alzheimer's disease left her incapable of living alone. Poor thing. I miss my grandma.
My grandparents let their Scotties (actually, they were our Scotties to start with, but my grandparents eventually appropriated them from us...long story) get like this too, due to a diet of roasted chickens and too little exercise. And believe me, a Scottie too fat to chase squirrels is a sad sight to behold.