There are a few other ways to get cats to lose weight:
Feeding wet food - it's not as calorie dense as kibbles
Feeding set amounts divided into 4 small daily meals and feeding like that means that all get finished fairly quickly and you can feed the glutton with the others
Having said that, I have a girl who was born to a feral mother on a rubbish dump and is so food driven that she tamed herself. When I try and limit her intake, she goes next door to eat the neighbour's cat's food. She remains a little blimp. Do take the teeth out, 10 isn't that old and you will have a much happier boy. Bacteria from dental disease can damage both the heart and the kidneys. Omega 3 oil is very helpful
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Hey thanks for the advice! I also considered putting collars on them for this kind of bowl that only gives access to the cat with the right collar on which sounds neat but I'm not sure if it's so effective at keeping him quiet (wife works at home).
Regarding the teeth, I'm not against their removal so to speak, but the anaesthesia at his age is a risk many vets aren't willing to take especially at his weight.
I don't want bad teeth to cause kidney diseases but at the same time I don't want him to die trying to reduce the risk of that. It's tricky...
Sadly, yes. Weight loss should be gradual to avoid complications with his liver because cats don't process fat very well but if you can get his weight down, it's worth a try. Don't reduce his food intake by more than 10% every couple of weeks. The Hills metabolic diet kibble actually worked well on my little butterball when I used it