Are those fire hose connections running alongside the right-hand building's fire escape? I wonder if they would've connected the bottom of that pipe to a pumper or to the hydrant across the road.

[They're standpipes of the type also seen in this post. - Dave]

What can go wrong here does go wrong here.

The infamous Bridge of Sighs from the interrogation rooms of the Doge's Palace to its prison cells comes to mind.

An early example is seen here. When they proliferated in urban architecture in the 1960s and '70s, a witty substitute name was "honky tube."

Does anyone know what a sample room is? Obviously it's associated with a billiard parlor.

[It's a bar. - Dave]

From the Encyclopedia of Chicago:

A second type of drinking place evolved from grocers and provisioners who began to sell hard liquor in wholesale quantities. At first, their sample rooms were places where customers could taste test the stock; long afterward, "sample room" became simply another name for saloon.

Murphy was an optimist.

also applied to the hotel. Demolished in 2007. Some photos of the demolition on Flickr.

[This is not the same building. - Dave]