He especially confronting the latter gang when their leaders Ike Marsh and Dutch Heinrichs began raiding the Hudson River Railroad yards and express trains.

While at Walling's Twentieth Precinct, he gained a reputation as a brave officer while posted in such notorious districts such as the Fourth Ward, Battle Row and Hell's Kitchen having notable successes against the gangs dominating those areas.

[1] McCullagh was attacked by Dutch Heinrichs and two of his henchmen in Hell's Kitchen while investigating the theft of two hogsheads of ham from a Hudson River Railroad freight car.

He battled the three men for over a half an hour before knocking all three unconscious with his nightstick and bringing in the gangsters single-handed to a nearby precinct on West Twenty-Fifth Street.

In particular was his assault by ex-police officer James G. Taylor who had previously been dismissed from the police force due to an official complaint made by McCullagh.

Taylor attempted to murder McCullagh, ambushing him one night on Ninth Avenue with a pistol, but the roundsman escaped with a minor head wound and a marked ear.

He remained bedridden for over a week until March 6 when he his condition unexpectedly worsened and a tracheotomy was performed by police surgeon William F. Fluhrer.