During the first decades of the 20th century, Charles Deneen was a major player in Chicago politics. He served two terms as Cook County State's Attorney and two terms as governor of Illinois. In 1924 he was elected to the U.S. Senate.
Deneen was one of the leaders of the reform wing of the local Republican Party. The party's other faction was headed by Chicago's mayor, Big Bill Thompson. The Thompson group had close ties to Al Capone and other questionable figures.
The two factions came into conflict during the 1928 primary season. Thompson was backing incumbent Robert Crowe for State's Attorney. Sen. Deneen supported the challenger, "honest judge" John A. Swanson. The campaign grew intense. Then the bombings started.
The homes of two prominent Thompson allies were hit with hand grenades. Deneen supporters had their homes attacked in retaliation. The slang for a hand grenade was "pineapple." So many of them were going off that the papers began referring to the campaign as The Pineapple Primary.
On March 21, unknown gunmen killed "Diamond" Joe Esposito, Deneen candidate for 19th Ward committeeman. The senator attended Esposito's funeral on the morning of March 26, then returned by train to Washington.
Shortly after 11 p.m. that evening, a bomb exploded on the porch of Deneen's home at 457 W. 61st Place. The blast tore away the front of the house and smashed all the windows. The windows of a dozen nearby buildings were shattered as well.
Awakened by the explosion, people rushed into the street. Police and emergency crews arrived. One of the neighbors said she'd heard the blast, then saw a man jump into a car and speed away. Now reporters descended on the scene, and they brought chilling news--a few miles away, the home of candidate Swanson had also been bombed.
No one was hurt in either incident. But the attack on Sen. Deneen's residence made national headlines. It was one thing for those barbarians in Chicago to shoot one another, but you did not bomb the home of a U.S. Senator. There were calls for an investigation by the U.S. Attorney General, and suggestions that President Coolidge declare martial law.
The Thompson faction claimed that Deneen and Swanson had bombed their own homes, to gain sympathy. Few people swallowed that one. In the April 10th primary, the entire Thompson-backed ticket lost. Swanson beat Crowe, and later won the general election for State's Attorney.
Charles Deneen ran for re-election in 1930, but lost in a violence-free primary. He died in 1940. His historic Englewood home still stands, and is privately owned.