concrete boots

It's a euphemism. You give someone concrete boots so he can sleep with the fishes. It's a way of ensuring his early retirement in lieu of other health-related issues like lead poisoning.

Probably refers to mobsters who were "rubbed out" (killed) by a rival mob, who then had their feet encased in concrete, their body eventually dumped in a nearby (deep) body of water.

Carl

Glass wrote:

Sometimes people get into a situation where they cannot afford more fashionable leather boots and are forced by circumstances into wearing concrete.

Unfortunately it is usually the LAST thing they wear.

Bret Cahill