Who is Sheila O’Brien, the retired judge pushing for a Jussie Smollett special prosecutor?

Is she a concerned citizen, or is she running to unseat Cook County State’s Attorney Kim Foxx? Or stoking the Smollett controversy for someone else?

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Retired judge Sheila O’Brien walks through the lobby of the Leighton Criminal Court Building after a hearing.

A Cook County judge on Friday will rule on retired judge Sheila O’Brien’s request to appoint a special prosecutor to investigate how State’s Attorney Kim Foxx handled the Jussie Smollett case.

Ashlee Rezin/Sun-Times file photo

Veteran Cook County Judge Michael Toomin on Friday is set to rule on whether to appoint a special prosecutor to probe State’s Attorney Kim Foxx’s handling of the criminal case against “Empire” actor Jussie Smollett. 

The petition now before Toomin was the first in a flurry of legal briefs and subpoenas filed by former state Appellate Court justice Sheila O’Brien. Starting in April, O’Brien’s filings have catalogued a long list of suspicious circumstances around the case, which was dismissed just weeks after Smollett was charged, despite what Chicago police say was “overwhelming evidence” Smollett staged a hoax hate crime. The State’s Attorney’s office, and some unbiased observers, say O’Brien’s speculations don’t pass the high bar needed to start a Robert Mueller-style inquiry.

Many wonder if O’Brien is angling to run for Foxx’s job, or trying to stoke the controversy on behalf of someone who is. After a hearing in May, O’Brien insists she is the rarest of Cook County creatures: a nobody whom nobody sent.

“I’m a private citizen. I was in public life for a long time,” O’Brien told reporters. “I did this because I think it’s the right thing to do and someone had to do it.”

O’Brien retired from the appellate court in nearly a decade ago and has been known since, if at all, for her activism within the Catholic church.

Since retiring in 2011, O’Brien said she spent time with her family or caring for elderly loved ones, occasionally working as a legal consultant. Her law license lapsed in 2014, and she has been filing her petitions and appearing in court “pro se,” as a lay person. At court appearances she has mentioned, wryly, that she is wearing borrowed outfits, because she hasn’t needed a business wardrobe for years.

In a curriculum vitae she submitted with a report as a judicial ethics consultant last year, O’Brien describes herself as a “lifelong Democrat.” She has been married for more than 25 years to Chicago native Wayne Andersen, who was an aide to Republicans Henry Hyde and Jim Edgar before becoming a Cook County judge in the 1980s. 

O’Brien grew up in downstate East St. Louis, where her father was a high-ranking police officer. O’Brien finished law school at Notre Dame and practiced in the St. Louis area, becoming a public defender in St. Clair County, and, in 1985, was appointed an associate judge in the downstate 20th Circuit. According to her CV, O’Brien was the first woman to serve as judge in the five-county circuit.

In 1991, she married Andersen. That year Andersen was appointed to a federal judgeship by President George H.W. Bush. O’Brien resigned from the 20th Circuit, and two days later was “recalled” by the State Supreme Court to fill a vacant seat on the Cook County bench —circumstances that several long-serving Cook County judges told the Chicago Sun-Times they had never seen before or since. In an email, O’Brien said she asked the high court to recall her, and then detailed a “warm story.”

O’Brien ran for an appellate court seat in 1994, winning the primary without the benefit of a party endorsement. Her campaign committee was chaired by Ald. Ed Burke (14th). Asked about her connection to Burke, O’Brien in an email said she “had been friends” with the alderman, now facing federal corruption charges, and his wife, state Supreme Court Justice Anne Burke.

O’Brien’s campaign contributor information was not immediately available, but Board of Elections records show she wound down her campaign account in 1999, meaning she raised less than $5,000 for her successful bid for reelection in 2004. 

O’Brien has written op-eds criticizing the Catholic church for its handling of sexual abuse allegations against priests and the church’s refusal to ordain women as priests — in a Chicago Tribune piece, she encouraged parishioners to direct donations to their local church, not the Catholic hierarchy in Rome.

O’Brien served on the fundraising committee for gubernatorial candidate Chris Kennedy and volunteering for several races for judge or municipal government posts.

Virginia Mann, a longtime friend, said O’Brien helped Mann’s unsuccessful campaign for a city council seat in Evanston. Friends have tried to get O’Brien to run for office herself.

“I wish she would run for some public office, senator, judge, or anything,” said Mann. “She has consistently said ‘absolutely not.’”

Toomin has ruled against nearly every motion O’Brien has filed to date, including a request to have a judge from another county make the decision on a special prosecutor. O’Brien has said she believes she can appeal a ruling that doesn’t go her way, and seems likely to continue her fight.

“Who’s going to go in?” she said after the last hearing. “Nobody has, so it seemed like the right thing to do. So, here I am.”

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