While judges set conditions of probation, the adult probation department assesses offenders' supervision levels and the likelihood they could break the law again.
Probation can be seen as preferable to prison because offenders can keep their jobs and maintain family ties, reducing the likelihood of committing new crimes, said Carl Wicklund, executive director of the American Probation and Parole Association.
But properly assessing and monitoring a probationer is critical, Wicklund said.
"The risk is always, you have a condition of supervision that you are supposed to be abiding by as a probationer and you don't abide by it and nothing happens — it just gives you the message that the rules don't really pertain to you," Wicklund said.
"And if the rules don't pertain to you in that, maybe they don't pertain to you in other ways," he said. "The justice system becomes a paper tiger."
Ward's path to adult probation began Oct. 23, 2011, when Chicago police arrested him for having a loaded Cobra .38-caliber pistol. Ward, identified by police as a Gangster Disciple, told officers he had the gun for protection.
He pleaded guilty and on Jan. 5, 2012, was sentenced to two years of probation, a punishment criminals often dismiss as getting "paper." The judge set special conditions for Ward, requiring him to earn his high school diploma and stay off the streets from 7 p.m. to 7 a.m.
Though Ward was a gang member and had been arrested eight times as a juvenile — including for alleged crimes involving violence — the probation department concedes it wrongly assessed him as a low risk to commit new crimes. He was given regular probation and had to report once a month.
It fell to veteran probation officer Dimitri Apostolovich to monitor Ward, who for the first few months dutifully reported to Apostolovich and obeyed his curfew, according to records.
About 9:15 p.m. on March 21, 2012, probation officers stopped by Ward's home, but he was nowhere to be found. Officers repeatedly went back to his home. Each time, he was not there.
Then, shortly before 2 a.m. March 28, 2012, Ward was out past curfew when Chicago police arrested him for allegedly riding in a stolen 2002 Saturn, according to police records. About two weeks later, he met with Apostolovich, who incorrectly noted in Ward's file that he had no new arrests.
Records show probation officers quit checking on Ward on April 4, 2012, even though his court-ordered curfew was supposed to extend for another three months. A notation in Ward's records recounts what happened when officers last visited his apartment: "Person Answering Stated Defendant Did Not Live At Address Officers Need More Information."
In July, Ward was arrested a second time for allegedly riding in a stolen car, an arrest the probation department later discovered.
Arrest records show he had moved. Yet, when Ward later reported for his monthly probation meetings, Apostolovich documented "No Address Changes."
The department and Apostolovich missed Ward's third arrest that year. An administrator at Hyde Park Academy High School called police on Nov. 26, 2012, after Ward repeatedly refused to leave school grounds, according to police records.
Police said Ward was standing "in front of the school Gang handshaking with other Gangster Disciple members" and charged him with criminal trespass.
Prosecutors allege Ward's violent battle with a rival gang faction had reached a flash point. One of Ward's friends had been killed, and fellow gang member Kenneth Williams had been shot and wounded.
On Jan. 29, Ward and Williams allegedly were seeking revenge when they drove past Harsh Park on the South Side. There, Hadiya and her friends had gathered under a canopy to avoid an afternoon rain.
Prosecutors allege that Ward, mistaking the group for gang rivals, jumped out of the car and fired a gun six times. Hadiya was fatally struck in the back, and two of her friends were wounded.