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The man was found unresponsive in the water then taken to University of Chicago Medical Center in critical condition.
The boy was in an alley when someone in a black Jeep fired shots, striking him in the abdomen. He was hospitalized in critical condition, police said.
The boat, carrying 16 people, capsized about 7:30 p.m. Officials are searching Lake Michigan for one person who was unaccounted for.
Deputy Sean Grayson has been fired and charged with murder for the shooting. He has pleaded not guilty. The family says the DOJ is investigating.