“Sluggo” Watson was a middling prize-fighter in the 20's, but one impressive win (where he had bet all the money he could get his hands on) allowed him to get out of the ring and into business, right after the market crash. He bought a cheap property in Crime Alley and opened a restaurant, which was moderately successful. When prohibition ended, he turned it into a bar, which was wildly successful.
He keeps the place spotless, me makes sure the staff are well-dressed, well-mannered and well-informed about the products. As a result, even in Crime Alley, the bar is a favorite city hot spot. The main difficulty is the pressure he's under from The Wound Ravens. No matter how much protection money he pays, they always seem to want more.