[5] During the American Civil War, Allen volunteered for service and became a junior officer in the 25th New York Infantry Regiment, D Company,[6] but he had resigned his commission as a Lieutenant by August 1861.

[9] Allen ran for alderman of New York City's 5th district in 1866 with the support of several factions of the Democratic party, including Tammany Hall.

It was also notorious for allowing women to visit the establishment in order to drink, dance and socialize with men, which was presumed to eventually lead them into prostitution,[2] one journalist claiming that the concert saloon caused "the ruin of more young girls than all the dive keepers in New York".

[11] Allen owned half a dozen similar establishments, among them the St. Bernard Hotel at Prince and Mercer Streets, as well as financed gambling dens and other "places of ill-fame".

[4] Allen was a supporter of the candidacy of the Garfield/Arthur ticket in 1880, serving as Vice President of the 4th Ward Young Men's Garfield and Arthur Club.

[18] In 1894, he was arrested again based on complaints by Pinkerton detectives for operating an illegal pool hall in New York City.

As he told the New York Sun, "The newspapers, which have been abusing me for years, and have made me out a sort of interesting desperado, say that I've got a pull.

Every time the police get a warrant for me, make a raid on it, and don't find any evidence of a poolroom, they say that I had a tip in advance.