A Chicago judge could decide this week whether the special prosecutor investigating possible conflicts of interest in Jussie Smollett’s criminal case has a conflict himself, the latest twist in a saga marked by turns and reversals since the Empire actor reported a racist, homophobic attack that police say he staged against himself.
Former U.S. Attorney Dan Webb, appointed six weeks ago to look into whether the office of top Chicago prosecutor Kim Foxx acted properly in abruptly dropping charges against Smollett, disclosed in a court filing this week that he co-hosted a 2016 fundraiser for Foxx and wrote her campaign a $1,000 check.
Judge Michael Toomin, who selected Webb, is expected to address the issue at a Friday hearing. But it’s not clear whether he is seriously considering yanking the federal prosecutor-turned-star lawyer from a case that has drawn worldwide attention and sparked debate about whether Chicago authorities have been too hard on Smollett or given him favorable treatment.
Stakes in the investigation are high. While Smollett maintains he was the victim of a real attack in January, the special prosecutor could seek to reinstate charges or bring new ones if he concludes the original charges were improperly dropped. Any such finding could also politically damage Foxx, who in 2016 became Cook County’s first black female state’s attorney.
Webb’s investigation includes looking into whether Foxx’s calls with a Smollett relative and an ex-aide of former first lady Michelle Obama influenced the decision to dismiss charges. While Foxx recused herself before that March decision, communications released later by her office showed she continued to weigh in on the case. Webb is a Republican; Foxx is a Democrat.
Webb, 74, is a widely respected, even legendary figure to many in legal circles. As U.S. attorney in the 1980s, he played a central role in a watershed corruption investigation called “Operation Greylord,” which sent dozens of Chicago judges and lawyers to prison.
And Webb has been the go-to for years for judges, agencies and companies seeking someone with legal gravitas to oversee their investigations. He was hired by the city of Chicago to review how City Hall attorneys handle excessive-force lawsuits against police, and issued a report in 2016 that concluded they don’t regularly hide or obstruct access to evidence. Many civil rights lawyers sharply criticized Webb’s conclusions, saying ample evidence disputed his findings.
The risk in not replacing Webb is that it could foster an impression that Cook County’s justice system is controlled by establishment figures who watch out for each other and occasionally pull strings to get VIP defendants like Smollett out of legal trouble.
The close-knit nature of Chicago’s legal profession — where apparent conflicts of interest crop up often — was demonstrated by Judge LeRoy Martin Jr. decision in May to transfer the decision to appoint a special prosecutor to Toomin, because Martin’s prosecutor son works for Foxx.
While members of the public may see Webb’s donations as tainting any findings by him, there’s no indication either Foxx or Smollett’s lawyers will press for his replacement. Smollett’s legal team opposed the appointment of any special prosecutor, arguing the case was handled properly and should have stayed closed.
Webb, in many ways, is the consummate insider. Co-chairman of the high-powered Winston & Strawn, his clients have included ex-Illinois Gov. George Ryan and tobacco giant Philip Morris. Last year, President Donald Trump asked Webb to represent him. Webb declined “due to business conflicts,” his law firm said at the time.
Webb’s explanation for why he didn’t mention the financial support of Foxx earlier was that he didn’t remember it until someone recently brought it to his attention. Such fundraisers at Winston & Strawn, he said, are common. Webb added that he had “no recollection” of attending the fundraiser.
Michael Helfand, a Chicago-based lawyer who runs a lawyer referral service in the region, says he understands why such a donation by Webb to Foxx might raise eyebrows. But he said it’s common for Chicago lawyers to donate to candidates for chief county prosecutor.
“And when you look on his career as a whole, Webb doesn’t have a blemish,” he said. “For anyone in the know, his reputation is beyond reproach.”
Toomin could try to replace Webb with a lawyer or state’s attorney from elsewhere in Illinois without deep ties across Chicago’s legal landscape. But even if Toomin were inclined to offer the job to someone else, there may be few takers.
When he announced Webb’s appointment in August, Toomin said attorneys from other counties showed little interest in an investigation that, no matter how it plays out, will inevitably spark outrage in some quarters.