Although Capone bodyguard Jack McGurn was never prosecuted in the St. Valentine’s Day Massacre, the theory endures that he was its mastermind.

For one thing, if Capone was behind the Massacre, it seems likely he would have had McGurn handle the details.

Also, McGurn would have had good reason to go after members of Bugs Moran’s gang. On March 7, 1928, he was hit in the chest and arm by machine gun fire in the McCormick Hotel. His assailants allegedly were the Gusenberg brothers, Peter and Frank, who less than a year later were two of the seven men killed in the St. Valentine’s Day Massacre. McGurn survived another hit attempt on April 27, 1928, when a car carrying four men opened fire with Tommy guns on McGurn’s Lincoln. McGurn jumped out of the car and ran for cover.

Undoubtedly, McGurn had a lot of enemies, but circumstances surrounding his murder seem to suggest it was payback for the Massacre. On February 15, 1936, McGurn entered a bowling alley at 805 Milwaukee Avenue with two other men. As they prepared to bowl, another man entered the building and ordered everyone to stand still. The two men who had come into the building with McGurn and the third man pulled guns and shot him several times.

Popular legend says a Valentine’s Day card was left on McGurn’s body but there is no evidence to support this. However, a note left at the front desk stated:

“You lost your dough and handsome houses, but things could be worse, you know, at least you haven’t lost your trousers.”

Two weeks later, McGurn’s brother, Anthony, was shot to death by three men in a Chicago pool hall after he said he knew who had killed his brother.