Ok, the fellow I was thinking about in Chicago was Ben Lewis, a recently elected black alderman who was selling insurance to his constituents in competition with syndicate backed people who already had that business locked up. Lewis was murdered in 1963.

Bill Granata and Charles Gross were also politicians or would-be politicians who ran afoul of the Outfit and were removed from this world.

More to be found here. Many more than I remembered. It looks like Chicago really did play by a more brutal set of rules than NY.

"When the snows fall and the white winds blow, the lone wolf dies but the pack survives."
Winter is Coming

Now this is the Law of the Jungle—as old and as true as the sky; And the wolf that shall keep it may prosper, but the wolf that shall break it must die.
As the creeper that girdles the tree-trunk, the Law runneth forward and back; For the strength of the Pack is the Wolf, and the strength of the Wolf is the Pack.