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Michael "Mickey" Segal

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Michael "Mickey" Segal (born 1944) is an insurance broker, business consultant, and legal advocate who lives in Chicago, Illinois. He began his career as a CPA and as an attorney. He led Near North Insurance, once the nation's fifth largest independent insurance brokerage, before a series of intense legal battles led to its destruction. He is the author, along with Pultizer Prize Winner Maurice Possley, of the book Convicted at any Cost.

Early Life[edit]

Michael Segal was born in the neighborhood of West Rogers Park in Chicago. His father was a fur salon owner who ran a local shop. After graduating from high school, Michal attended Loyola University of Chicago, and then went on to Depaul University Law School. He attended school with future Chicago Mayor Richard Daley.


Near North Insurance[edit]

Michael began his career working full-time as a certified public accountant. He got involved in Chicago politics, and became connected to Chicago ward boss George Dunne, the famous Cook County Board of Commisioners President who was part of the Daley "political machine"[1]. Segal provided financial services to an insurance brokerage called Near North Insurance that Dunne founded before joining the firm full-time, and eventually buying Dunne out.

Segal ran Near North Insurance for three decades. It became the fifth largest independent insurance brokerage in the United States. The firm did business with fortune 500 companies, provided coverage to Chicago institutions like O'Hare International Airport, McCormick Place and the Chicago Housing Authority[2], insured casinos in Las Vegas, movies in Hollywood (like Arnold Schwarzenegger's "Terminator 3"),[3] and even counted Oprah Winfrey's Harpo Studios as a client.[4] Segal did business with the brother of Mayor Richard Daley, John, among other political figures[5], and became a player in Chicago politics[6]. During Segal's trial, Chicago press, including the Tribune, alleged Segal's political connections helped Near North's business dealings by orchestrating "sweetheart deals"[7].

FBI RAID[edit]

In January 2002, Segal was raided by the FBI.

He was intercepted at the Westin Hotel and was questioned for hours about an unnamed public corruption case[8]. He was also accused of financial crimes. Government prosecutors alleged that Segal mismanaged a premium trust account, and accused him of defrauding his clients, and embezzling $20 million[9].

Segal's connections to prominent Chicago politicians made the story a sensation in the local press. Attorney Patrick Fitzgerald, who would soon become famous for prosecuting Illinois Governor Rod Blagojevich and for his role in the Plame Affair, had recently been named U.S. Attorney for the Northern District of Illinois[10] and was overseeing the case. He was tough and aggressive and determined to change the culture of corruption in Illinois politics[11]. Chicago Magazine described the raid he ordered on Segal as a melodramatic tactic that was straight out of Rudy Giuliani’s playbook.

Law enforcement wanted Segal to wear a wire, listen in on his political connections' conversations[12], and help them build public corruption cases. If he didn't take the offer and "play ball", he was threatened with a variety of charges - ranging from fraud to racketeering.[13] Under Fitzgerald, the U.S. Attorney's office was clear about their intentions: they wanted to "flip" connected Chicago businesspeople, get them to cooperate, and make cases against other, prominent Chicago political leaders.[14] Even though the financial accusations against Segal were serious, to many journalists it was clear that prosecutors were focused on larger targets.[3]

Yet Segal would not cooperate. He refused the FBI offer,[3] and claimed to have no knowledge of criminal activity or financial wrongdoing. He had never been accused of any crime of any sort, and was determined to not be painted as a criminal. A high-profile series of legal battles soon commenced.[15]

UNITED STATES vs Segal[edit]

The trial was contentious. Prosectors were unusually aggressive[16] for a case that revolved around a regulatory issue. Segal's attorneys were also vocal. They contended that as the case was rooted in a regulatory infraction, no crime had actually been committed. Their argument was bolstered by the fact that no money was stolen, and that none of Segal's clients ever reported a loss of service or finances.[17] They claimed law enforcement was targeting Segal to scare his political connections[14], and the charges against Segal were an attempt to bully him into supporting the goal of the original FBI raid.[13] Even though prosectors conceded the fact that none of Segal's clients ever suffered a loss and no money was taken, they pressed on, asserting that accounts were still managed illegally.

The case dominated Chicago headlines as details of Segal's business[18] and stories of corporate sabatoge were detailed in testimony. It came to light that a group of former Near North employees, who were intent on taking control of the company, were behind the FBI case. They had illegally hacked the company's servers[19] and databases and attempted to paint Segal as a thief[4]. Segal's attorney's also revealed a paper trail that indicated Near North's rivals in the insurance industry were supporting the former employees.[20] This made further headlines, as the insurance firms had histories of bare-knuckle competition and corporate espionage.[21]

In court the prosecution was led by a William Hogan, an assistant United States Attorney who had a reputation for unethically tampering with evidence.[22] Hogan had became infamous in legal circles over his involvement in the scandalous "El Rukn" trial, a saga that culminated with a former gang member being awarded $22 million in damages[23] for wrongful prosecution, and with Hogan himself being fired[24] from the Justice Department. Hogan had to force his way back to government employment through litigation, and numerous Chicago media outlets speculated his zeal for Segal was born of a desire to score a high-profile "win".[25]

Eventually, Segal lost.[26] The case was seen as the opening salvo in Patrick Fitzergald's quest to take on Illinois political figures[27], as he soon launched his case against George Ryan.

Post Trial and Later Work[edit]

Prosectors pushed the judge to order an unuslaly long prison term[28] for a non-violent financial infraction for which there were no victims. Segal fought against this scare-tactic yet was still sentenced to ten years of incarceration.[7] Segal unsuccessfully fought his conviction[29] as he served his sentence, hoping for a reversal, or for early release.[30] Yet he served nearly his entire sentence, and was released only four months early from prison in 2012. [31] Once freed, he moved back to Chicago.[32]

Following his release, Segal began to try and recover assets[33] his lawyers asserted were unjustly seized by the government[17]. In interviews, he also began openly discussing writing a book[34].

In 2014, a civil case the government brought against Segal in U.S. tax court determined that he could not be found liable for fraud[35]. This was significant because tax courts have a lower burden of proof than federal courts, and the court cited the same evidence used to convict Segal in 2004. It gave validity to his legal team's long held claim that a supposed regulatory infraction should not be treated as a federal crime.

In 2016 he was able to convince an appellate court to cut his forfeiture order in half, and he won a judgement that allowed him to reacquire his minority investment in the Chicago Bulls NBA franchise, a development which his friend and Bulls majority owner Jerry Reisndorf was speculated to have been very happy about.[36]

In late 2016, after courts and commentators began at long last to recognize the validity of his legal claims[37], Segal began working with Maurice Possley, a Pulitzer Prize winning journalist (formerly of the Chicago Tribune) known for his work covering wrongful convictions and prosecutorial misconduct [38] on a memoir reflecting on his legal ordeal.


  1. King, Seth S. "George Dunne, Aide to Daley, Named His Succesor As Chairman of Cook County Democratic Committee". Retrieved 2018-09-13.
  2. "Dunne and Segal partnership powered brokerage's growth". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  3. 3.0 3.1 3.2 "Mickey Segal: The Hollywood movie". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  4. 4.0 4.1 "Insurer Segal files big lawsuit". tribunedigital-chicagotribune. Retrieved 2018-08-29.
  5. "Daley brothers talk--just not to each other". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  6. "Segal diverted funds to politicians: Prosecutors - Business Insurance". Business Insurance. Retrieved 2018-09-14.
  7. 7.0 7.1 "Segal gets rebuke, 10 years". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  8. "The New Face of the Law". Chicago magazine. Retrieved 2018-09-14.
  9. "Segal insurance firm, former bookkeeper are indicted". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  10. "The New Face of the Law". Chicago magazine. Retrieved 2018-09-13.
  11. consultant, Dennis Byrne. Dennis Byrne is a Chicago-area writer and public affairs. "Dealing with a new set of rules". chicagotribune.com. Retrieved 2018-09-14.
  12. Gradel, Thomas J; Simpson, Dick (December 19, 2014). Corrupt Illinois: Patronage, Cronyism, and Criminality. ISBN 9780252097034. Search this book on Amazon.com Logo.png
  13. 13.0 13.1 "FBI sought help from Segal". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  14. 14.0 14.1 "Rest insured, political pals feel Segal's pain". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  15. "Federal judge clears way for Segal trial in April". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  16. "Insurance tycoon may face new charges in fraud case". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  17. 17.0 17.1 "Fall From Grace | Leader's Edge Magazine". leadersedgemagazine.com. Retrieved 2018-06-26.
  18. "Segal's lawyers push for hearing". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  19. "Firm sues ex-employees over hacking". tribunedigital-chicagotribune. Retrieved 2018-08-29.
  20. "Dueling moguls: Aon vs. Near North". April 1, 2002.
  21. "Chicago brokers battle over stamping ground". June 2002.
  22. "Prosecutor accused of meddling in civil lawsuit". April 29, 2015.
  23. Cherney, Jason Meisner, Elyssa. "Jury awards $22 million in damages to wrongly convicted ex-El Rukn". chicagotribune.com. Retrieved 2018-06-26.
  24. "The Trials Of William Hogan". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  25. COHEN, SHARON (1998-11-15). "Prosecutor Wins Way Back to Right Side of Law". Los Angeles Times. ISSN 0458-3035. Retrieved 2018-06-26.
  26. O'Connor, Matt. "Segal found guilty". chicagotribune.com. Retrieved 2018-06-26.
  27. Kass, John. "Rest insured, political pals feel Segal's pain". chicagotribune.com. Retrieved 2018-09-14.
  28. "Segal prosecutors push for a longer prison term". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  29. "Segal fights racketeering conviction". tribunedigital-chicagotribune. Retrieved 2018-06-26.
  30. "From Pinstripes to Prison Stripes: Near North's Segal on Life Behind Bars". Insurance Journal. 2006-01-01. Retrieved 2018-06-26.
  31. "Michael Segal released from prison 4 months early - Business Insurance". Business Insurance. Retrieved 2018-06-25.
  32. "'Mickey' Segal freed from federal prison". ABC7 Chicago. Retrieved 2018-09-14.
  33. "Requiem for a Heavyweight?". Chicago magazine. Retrieved 2018-09-14.
  34. "Fall From Grace | Leader's Edge Magazine". leadersedgemagazine.com. Retrieved 2018-06-26.
  35. "U.S. drops civil charge against Mickey Segal". Crain's Chicago Business. February 13, 2014.
  36. Janssen, Kim. "Give ex-con Mickey Segal back his stake in the Chicago Bulls, court says". chicagotribune.com. Retrieved 2018-06-25.
  37. "Near North Insurance's Mike Segal appeals to U.S. Supreme Court - Business Insurance". Business Insurance. Retrieved 2018-06-26.
  38. Possley, Maurice (2013-08-29). "How Two Newspaper Reporters Helped Free an Innocent Man". The Atlantic. Retrieved 2018-06-25.

External Links[edit]

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