Dan Webb
Partner
Co-Executive Chairman
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Dan is co-executive chairman of Winston & Strawn and one of the most distinguished and sought-after trial lawyers in the United States. He has tried more than 100 jury cases involving a wide variety of claims and been named a fellow of the prestigious American College of Trial Lawyers. Notably, Dan achieved international acclaim for his successful prosecution of retired Admiral John Poindexter in the Iran-Contra Affair. He served as the U.S. Attorney for the Northern District of Illinois and has served in special prosecutor or similar roles on several occasions, including for the successful prosecution of actor Jussie Smollett in Chicago, for which he was named Am Law’s “Litigator of the Week” in December 2021.
Key Matters
Special Prosecutor and Similar Appointments
Dan has been appointed by courts to act as a Special Prosecutor or in a similar capacity on five occasions. As these appointments reflect, in numerous sensitive and high-profile legal matters of great public interest, various courts have placed their confidence in Dan to serve as an independent prosecutor with integrity and the highest level of professionalism.
Prosecution of National Security Adviser John Poindexter–Iran-Contra Affair: In 1990, Dan was appointed as a Special Prosecutor in the Iran-Contra scandal to conduct the trial of Vice Admiral John M. Poindexter, who served as the National Security Advisor under the administration of President Ronald Reagan. Mr. Poindexter was charged with conspiracy, lying to Congress, and obstruction of Congress in connection with a Congressional investigation into whether high-ranking officials in the Reagan administration improperly facilitated the sale of arms to Iran in exchange for the release of American hostages held in Lebanon, which became known as “The Iran-Contra Affair.” During the trial in this matter, which took place in the U.S. District Court for the District of Columbia, Dan cross-examined President Reagan and Lieutenant Colonel Oliver North, who was a staff member of the National Security Council. Mr. Poindexter was convicted of all charges. (His convictions were later reversed on the grounds that witnesses may have been influenced by certain immunized testimony that Mr. Poindexter had given before Congress.)
Investigation and Prosecution of Election Fraud and Corruption: In 1989, Dan was appointed as a Special Prosecutor by Judge Richard Fitzgerald, the Chief Judge of the Criminal Courts in Cook County, Illinois, to investigate potential fraud and corruption in connection with elections in Cook County. The investigation included potential fraud and misconduct within the Cook County State’s Attorney’s Office, which was then run by Cook County State’s Attorney Richard M. Daley, who later was elected Mayor of Chicago, a post he held for 22 years. As Special Prosecutor, Dan prosecuted and secured the convictions of more than a dozen individuals on charges relating to improper election-related conduct, including several individuals who were current or former employees of the Cook County State’s Attorney’s Office.
Investigation of High-Ranking Government Official: In the late 1980s, the U.S. Court of Appeals for the District of Columbia Circuit, Division for the Purpose of Appointing Independent Counsels (MacKinnon, J.), pursuant to the Ethics in Government Act of 1978 and the Independent Counsel Statute, 28 U.S.C. Section 591, et seq., appointed Dan as Independent Counsel to investigate certain allegations regarding potential violations of federal law by a high-ranking government official. After a thorough investigation, Dan determined that there was insufficient evidence to bring a prosecution and filed a report with the Independent Counsel court; the matter was then sealed.
Investigation and Prosecution Regarding Death of David Koschman: In 2012, Dan was appointed by the Circuit Court of Cook County to serve as Special Prosecutor in connection with an investigation of the 2004 death of David Koschman. This pro bono matter was a headline-grabbing case in Chicago. Winston attorneys led by Dan were appointed to serve as Special Prosecutor and Deputy Special Prosecutors tasked with investigating the homicide of 21-year-old David Koschman, who died after an April 25, 2004, incident in Chicago’s nightlife district, during which Koschman was punched by a 29-year-old man later identified as Richard Vanecko—the nephew of then-mayor Richard M. Daley. The force of the punch knocked Koschman backwards; he hit his head on the pavement and sustained fatal skull fractures. In 2004, the Chicago Police Department (CPD) and Cook County State’s Attorney’s Office concluded that they could not determine if Koschman was punched or pushed or if it was Vanecko who struck Koschman, but that whoever struck Koschman acted in self-defense. In January 2011, the Chicago Sun-Times issued a FOIA request to the CPD seeking records relating to the Koschman case. The CPD reinvestigated the case in early 2011 and concluded that Vanecko punched Koschman while acting in self-defense and that charges were not warranted. Dan and a team of Winston & Strawn lawyers empaneled a special Cook County grand jury, interviewed 146 witnesses, reviewed 300,000 pages of documents, obtained an indictment and conviction of Vanecko, and wrote a 162-page report, containing 852 footnotes, detailing the deficiencies by police and prosecutors in their previous handling of the case.
Investigation and Review of FCRL Division of City of Chicago Law Department: Dan was retained by the Law Department to The City of Chicago, through its Corporation Counsel, Steve Patton, to conduct a comprehensive, independent investigation and review of the Federal Civil Rights Litigation (FCRL) Division of Chicago’s Law Department. Acting entirely independently, Winston reviewed the FCRL Division’s policies, procedures, and practices and recommended changes to ensure that such policies, procedures, and practices conform to the highest professional and ethical standards and best litigation practices. At the completion of the review in July 2016, the firm issued a written report, summarizing its investigation and recommendations and the status of the FCRL’s implementation of those recommendations. This matter was done on a partial pro bono basis.
Investigation, Review, and Prosecution Regarding Jussie Smollett: Most recently, Dan was appointed to serve as Special Prosecutor, with support from Deputy Special Prosecutors Sam Mendenhall and Sean Wieber and a team of associates and other professionals, in connection with the case of Jussie Smollett, the well-known actor who claimed that he was the victim of a hate crime attack in Chicago in January 2019. Dan’s investigation began August 23, 2019, at the request of Cook County Circuit Court Judge Michael Toomin. He was tasked with determining whether Smollett should be further prosecuted for false reports to Chicago police and whether any person or office involved in the case—including the Cook County State’s Attorney—engaged in wrongdoing.
In February 2020, Dan announced plans to further prosecute actor Jussie Smollett, with a special grand jury returning a six-count indictment of felony disorderly conduct for lying about a hate crime. Dan said, “the grand jury’s investigation revealed that Jussie Smollett planned and participated in a staged hate crime attack, and thereafter made numerous false statements to Chicago Police Department officers on multiple occasions, reporting a heinous hate crime that he, in fact, knew had not occurred.” While Dan said he disagreed with Cook County State’s Attorney Kim Foxx’s handling of the case, he did not find that the office engaged in wrongdoing. The investigation report prepared by the Special Prosecutor’s team was unsealed by Judge Toomin on December 20, 2021.
On November 29, 2021, the criminal trial of Jussie Smollett commenced, with Dan leading the prosecution. After seven days of trial, the jury returned a widely reported (by the U.S. and non-U.S. broadcast and other media) and celebrated win for Dan and the team, finding Smollett guilty of five of the six counts of disorderly conduct. As Dan stated after the trial, “That verdict was a resounding message by the jury that, in fact, Smollett did exactly what we said he did”— planned and orchestrated a fake hate crime and lied to the police about it. The remarkable win was recognized by Am Law, which bestowed upon Dan and the team its highly coveted “Litigator of the Week” honor. At sentencing, Judge James Linn sentenced Smollett to 150 days in county jail, fined him US$25,000, and ordered him to pay more than US$120,000 in restitution for the overtime spent by Chicago police officers investigating his false reports.