Hispanic male Alejandro Aguado, age 22, was walking with two friends just after midnight on May 28, 2019 along the 606/Bloomingdale Trail near the 1800 block of North Monticello Avenue in Chicago's Logan Square.
Three males approached the group and asked about their gang affiliation; when the friends denied any ties, gunfire erupted.
Alejandro Aguado was struck in the chest and back and was rushed to Norwegian Hospital, where the 22-year-old was pronounced dead in the early morning
darkness, the quiet of the elevated path broken by the sudden swirl of squad cars and flashing lights.
In the chaos that followed, a 19-year-old woman was hit in the abdomen and taken to Mount Sinai in critical condition, and a 20-year-old man suffered a wound to his lower backside and was stabilized at Stroger Hospital.
Surveillance footage captured three suspects sprinting eastbound along the trail moments after the shooting, silhouettes disappearing into the city before officers could close the distance.
The 22-year-old victim Alejandro Aguado identified as being from Portage, Indiana, had been a young father, a detail that sharpened the loss for relatives and friends who gathered in grief as word spread.
Detectives canvassed the neighborhood and the viaducts, releasing images and asking the public for help in identifying the three suspects seen fleeing the scene.
In the days and weeks that followed, police emphasized that the attack appeared to have been sparked by the question about gang affiliation, a ritual that turned deadly despite the victims' denials.
As spring turned to summer, no arrests were announced; months later, Alejandro's family publicly pleaded for information, still searching for answers and urging anyone with knowledge of the three assailants to come forward.
He was memorialized by loved ones who recalled the Alejandro's warmth and the easy way he moved between family in Northwest Indiana and the Southeast Side, a life anchored in everyday joys cut short on a trail better known for joggers and cyclists than for crime scene tape.
As of September 2025, case file on Alejandro Aguado remains open, no suspects have been named, leaving the police to still plead to the public for any tips that may lead to an arrest.
