Far North Side man charged with attempted murder after extremely short police investigation

Leonard Dillard | CPD

Update February 16, 2022: Leoanard Dillard pleaded guilty to one count of aggravated battery by discharging a firearm in a deal with prosecutors who dropped 12 other felonies including multiple counts of attempted murder and weapons charges. Judge Shelley Sutker-Dermer oversaw the case and sentenced Dillard to 11-1/2 years. He is scheduled to be paroled on September 15, 2028.


It may be the shortest and most successful shooting investigation that Chicago has seen in years.

Police responding to a call of a person shot in the 6200 block of North Leavitt last Tuesday evening arrived to find a man and his neighbor in the alley.

Per a police report, the entire investigation unfolded thusly:

Officers asked the men, “Who’s shot?”

“Victim related…that he was shot.”

“Arrestee then spontaneously uttered…’I shot him.’”

With that, 48-year-old Leonard Dillard was placed into custody for shooting his 23-year-old neighbor during a dispute, police said. The victim was taken to St. Francis Hospital in Evanston where his condition was stabilized.

Dillard is charged with attempted first-degree murder and Class X felony aggravated battery by discharging a firearm. He was ordered held without bail by Judge John Lyke.
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About CWBChicago 4363 Articles
CWBChicago was created in 2013 by five residents of Wrigleyville and Boystown who had grown disheartened with inaccurate information that was being provided at local Community Policing (CAPS) meetings. Our coverage area has expanded since then to cover Lincoln Park, River North, The Loop, Uptown, and other North Side Areas. But our mission remains unchanged: To provide original public safety reporting with better context and greater detail than mainstream media outlets.