For more than a year, Antwaun McLaren kept a spotless record while serving probation for a cocaine possession conviction, regularly checking in with his Cook County probation officer and passing urine tests to make sure that he remained drug free.

But unable to find work, the 23-year-old father of two, including a newborn son, had his cellphone service cut off after falling behind on his bill. When he missed his probation officer’s calls, McLaren found himself back in court, standing before Judge Diane Gordon Cannon in early 2018 for violating probation.

McLaren expected to be kept on probation after a brief hearing. He didn’t know that Cannon had a history of being tough on violators.

Cannon has sent some 1,450 defendants to state prison for violating probation, about 35% of those who appeared before her on such violations and the most of any judge currently on the Cook County bench, an unprecedented analysis of two decades of court data by The Circuit has found.

By contrast, dozens of past and present judges who heard a similar number of probation violations — for picking up a new charge, missing check-ins or skirting other rules — sentenced on average 13% of the defendants to state prison, according to the investigation by The Circuit, an investigative collaboration of the nonprofit news organizations the Better Government Association, Injustice Watch and The Chicago Reporter.

On that January day, Cannon ordered McLaren held without bond in the Cook County Jail until a hearing on the probation violation could be held. He remained in custody for two months before prosecutors dropped the matter.

Despite the fact that it was McLaren’s first run-in with the law as an adult, Cannon implied that he was part of a gang or mob, McLaren recalled in an interview. He said he felt Cannon’s animus toward him as a Black man caught up in the criminal justice system.

“Don’t look at me like I’m nothing. Still respect me as a human being,” McLaren said. “I can’t even pay a phone bill. What criminal organization am I in?”

Attorneys — many of whom spoke on condition of anonymity out of fear of retaliation by Cannon and other judges — said Cannon has a long history of bullying behavior and verbal outbursts from the bench, insensitivity toward minorities and a noticeable prosecution preference.

Cannon, who is white and a veteran of nearly 25 years on the bench, did not return repeated calls and emails seeking comment. Judge LeRoy Martin Jr., who presides over the court’s criminal division, said in an emailed response Cannon has been on paid sick leave from her $206,400-per-year job since the beginning of 2020 and is not seeking retention in the November election to stay on the bench.

The court’s most substituted judge

Cannon’s record of harsh treatment toward defendants and verbal outbursts, as well as her reputation for being pro-prosecution, may have led to another dubious distinction: Over the last couple of years, attorneys, using an obscure legal maneuver, have bounced her off more cases than any other judge atin Cook County’s central criminal courthouse, the analysis found.

Criminal cases are randomly assigned to judges by computer. Under state law, defense attorneys and prosecutors can opt for a different judge once — twice in murder and a handful of other serious offenses. No specific reason has to be given, but the motions for a “substitution of judge,” or SOJ, must be filed within 10 days of a judge being assigned. Motions to substitute can still be made later, but attorneys then must show that a judge is prejudiced against them — a difficult hurdle to overcome.

Attorneys quickly removed Cannon from nearly one of every five cases cases randomly assigned to her in 2018 and the first half of 2019, far more than any other judge, according to the analysis. 

The high number of SOJ motions against Cannon showed just how much she is viewed as biased and unfair and should raise concern among top court officials about her conduct, attorneys said.

Thomas Geraghty, a longtime professor at Northwestern University’s Pritzker School of Law, called on Martin and Cook County Chief Judge Timothy Evans to track SOJs as one indicator of whether judges are up to the task of dispensing justice fairly.

“If judges are getting a lot of these motions … there should be some process for figuring out is there a problem with the judge,” Geraghty said in an interview.

Evans and Martin declined to be interviewed for this story, but Mary Wisniewski, the chief judge’s spokeswoman, issued a statement saying court officials do not track SOJs because they are not “a reflection of judicial performance,” noting that the motions can be filed “for any reason.”

But lawyers who regularly frequent the county’s main criminal courthouse at 26th Street and California Avenue said they share their take with one another on the judges presiding there, giving them a good sense of their qualifications. 

In time, more veteran attorneys get a good feel for how a host of judges behave, including whether they treat defendants and their lawyers with respect, show balance in their rulings, and sentence uniformly and fairly.

Their reasons for substituting a judge can be many but often involve concerns about a judge’s reputation for fairness.

“A lawyer makes up their mind by knowing the customs (of) that particular judge,” said John DeLeon, a longtime criminal defense attorney in Chicago.

If there are concerns, attorneys don’t hesitate to switch judges, DeLeon said.

Cannon was bounced from at least 56 cases in 2018, almost 16% of the approximately 360 cases randomly assigned to her, the analysis found. Lawyers for four more defendants — allowed to SOJ two judges each because they faced the most serious felonies — also blocked Cannon’s appointment that year after first substituting other judges, records show.

No other judge even came close. The judge with the second most SOJs that year had 32, the analysis found.

Of the 33 Cook County judges who were assigned at least 300 criminal cases in 2018, seven didn’t have a single SOJ filed against them, according to the analysis. Another 10 judges had only one or two SOJs on their record for that entire year.

Questions of demeanor and impartiality

The criticism against Cannon for her temperament and fairness goes back years. 

Angered two years ago when she caught an intern for the public defender’s office texting on his cellphone in the midst of a bench trial, Cannon took possession of the phone and read the texts aloud before tossing the young man from her courtroom, according to several attorneys in the courtroom at the time, as well as the defendant whose case was being heard.

“She was highly pissed,” said Flamond Williams, now 39, who was on trial on a weapons charge in March 2018 and recalled that Cannon almost threw out an assistant public defender along with the intern, both of whom were waiting to be heard on other matters. Cannon eventually found Williams guilty.

Attorneys said they were aware that a complaint against Cannon over the incident had been filed with the Illinois Judicial Inquiry Board, the state agency that investigates allegations of judicial wrongdoing but rarely leads to consequences for judges. All complaints filed with the board are kept confidential until and whether administrative charges are filed. No findings have been made public on the matter.

That June, the Cook County public defender’s office halted assigning the same attorneys every day to Cannon’s courtroom, a longtime practice that the office has continued elsewhere at the courthouse at 26th Street and California Avenue.

In an emailed statement, Cook County Public Defender Amy Campanelli chalked up the change to a pilot project designed to keep her assistants on a case all the way from its inception to conclusion. No additional courtrooms besides Cannon’s have been added since then, though the office said it plans to expand the pilot project next month.

Tatyana Lewis, a Black woman who was sentenced by Cannon in 2018 to two years in prison following her guilty plea to a low-level felony drug possession charge, said she struggled to understand why, as a first-time offender, she didn’t instead receive community service with drug treatment.

Cannon, she said, lacked empathy.

“She’s got like this attitude, ‘This is my courtroom, you’re the criminal,’” Lewis said. “I don’t feel like she’s right for the community … especially someone who judges off of personal feelings or how they woke up this morning.”

Favoring the prosecution — except against cops

Cannon, who worked her entire career as a Cook County assistant state’s attorney before she was elected to the bench in 1996, has a reputation for favoring the prosecution — except when law enforcement officers face criminal charges.

She gained notoriety in 2015, when she acquitted Chicago Police Cmdr. Glenn Evans in a high-profile case on charges of shoving his gun into a man’s mouth. Cannon gave little credence in her ruling to evidence that the alleged victim’s DNA was found on Evans’ firearm.

Two years later, special prosecutors handling charges against three Chicago cops accused of conspiring to cover up the wrongful 2014 shooting death of Black teen Laquan McDonald by a white officer quickly substituted Cannon after she was randomly assigned the hot-button case.

“There’s no question that if I were the (special) prosecutor that I would have done what they did,” said G. Flint Taylor, a longtime civil rights attorney in Chicago. Taylor substituted Cannon on a post-conviction matter involving a client who alleged that he had been tortured by Chicago police detectives working under Cmdr. Jon Burge, who died in 2018. Taylor noted that Cannon had worked in the state’s attorney’s felony review unit at the time of Burge’s wrongdoing. 

“She’s one of the last surviving judges out there who has a direct connection with the Burge torture era,” said Taylor, calling Cannon’s courtroom style “authoritarian.” “It’s not surprising that defense lawyers, particularly in cases where police would be involved, would recuse her.”

From January 2018 through June 2019, attorneys substituted Cannon in at least six cases involving charges of battery to cops, the analysis of the court data found.

Lawrence Kennon, a Chicago attorney for more than 50 years, said his experience defending a Black woman years ago on charges of assaulting a police officer solidified, for him, Cannon’s reputation as a “cops’ judge,” especially for defendants of color.

Kennon, who died last month at age 91, was Black as well and thought his race also played a role in the judge’s treatment of him. He said in an interview in June that Cannon repeatedly cut him off during discussions with the judge and prosecutors in her chambers.

“She said, ‘Don’t interrupt. Listen to the other side,’” Kennon said. “She really did not want to hear the defendant’s side.”

‘You call that a report?’

Attorneys said Cannon’s animosity toward the defense could be open and obvious at times.

In a rare move in March 2012, an Illinois appellate court reassigned a murder case to another judge after reversing Chad Johnson’s conviction and rebuking Cannon for prohibiting the defense from questioning a Chicago police detective at trial about changes in a key eyewitness’s account.

The opinion also chastised Cannon for her personal comments in front of the jury on the quality of the defense evidence and the diligence of its investigator.

“You call that a report?” court records quoted Cannon saying as the investigator testified to the jury. 

The defense presented three witnesses who testified that they were with Johnson in Kentucky at the time of the drive-by shooting on Chicago’s South Side that killed Christopher Dorbin and wounded three others on Super Bowl Sunday in 2004.

In the appeal, attorneys for Johnson wrote that Cannon acknowledged that she had raised her voice after hearing the investigator’s testimony, but that the judge refused to preserve audiotape evidence that would have let the appellate court “hear for itself the tone of voice with which it taunted defense counsel and verbally accosted his witness.”

In a retrial in 2018, a Cook County jury acquitted Johnson, who has alleged in a pending lawsuit that Chicago police framed him for the murder.

In another long-running dispute, Cannon refused for months to step aside from overseeing Malvin Washington’s murder case, despite defense allegations that she had openly shown bias.

His previous attorneys had also alleged that Cannon unfairly favored the prosecution in her trial rulings, inappropriately scolded the defense lawyers in front of jurors, and treated Washington’s family with disdain.

In 2012, the Illinois Supreme Court upheld an appellate court’s decision to overturn  Washington’s first-degree murder conviction for the 2004 killing of Marquis Reed and wounding of a second man, ruling that Cannon had erred by refusing to let jurors consider second-degree murder charges.

At a hearing in 2017, Washington’s lawyers — with the Bluhm Legal Clinic at Northwestern’s law school — said they had been told that Cannon had mocked them behind their backs, calling Jeffrey Urdangen “Mr. Underpants” and Alison Flaum “Ms. Phlegm.”

Cannon denied the name-calling and accused Urdangen of telling people that he hoped she would die of cancer — an allegation that Urdangen denied.

The next week, Cannon abruptly reversed herself, withdrawing from the case.

At a retrial before a different judge, Washington was convicted by a jury of second-degree murder and was sentenced to 25 years in prison — far less than the 65-year sentence that Cannon had earlier imposed.

A life disrupted for a minor infraction

When Cannon sent McLaren to jail for missing the check-in with his probation officer two years ago, the toll of the two months in custody crippled his physical and mental health, said McLaren, who was already on disability for serious medical issues. 

McLaren said he became so ill he was unable to move from his cell bed and battled thoughts of suicide and fear he would die in custody. 

“That was the worst time of my life,” he said. “Three strokes didn’t compare to that.” 

McLaren wasn’t released from the jail until prosecutors — at the urging of his attorney — withdrew the probation violation, taking the issue out of Cannon’s hands. 

McLaren said the jailing cost him a chance at a job, disrupted his second year at Kennedy-King College, and put him in a tailspin that he’s still struggling to overcome.

Data analysis for this story was conducted by Forest Gregg and Hannah Cushman Garland of DataMade and Jared Rutecki of the BGA.