‘Conviction at Any Cost’: The Tangled Case of Michael Segal

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Michael Segal. www.MichaelSegalDueProcess.com

In December 2005, wealthy Chicago insurance broker Michael Segal was sentenced to a 10-year prison term in a widely covered $30 million fraud and racketeering trial. “You thought you were above the law,” the judge told him.

Segal, then 63, denied everything. “I am not a bad person,” he insisted. “I have never stolen a dime.” As it turned out, there was a lot more to the case than the headlines indicated. In a forthcoming book written with Pulitzer Prize-winning investigative journalist Maurice Possley, Segal, who served eight years of his sentence, argues he was a victim of a vindictive campaign by government lawyers angered by his refusal to help them in a wider investigation into white- collar crime.

 In a conversation with The Crime Report’s Dane Stallone about the book, “Conviction at Any Cost: Prosecutorial Misconduct and the Pursuit of Michael Segal, ” Possley, now a senior researcher for the National Registry of Exonerations, explains why Segal’s story illustrates the vulnerability of individuals, regardless of their wealth, to prosecutorial misconduct, why such misconduct is rarely disciplined, and how trials can sometimes hinge on the irresponsible rhetoric of a prosecutor determined to win at any cost.

This transcript has been condensed and edited for clarity.

TCR: One of the chapters in the book begins with a quote from Baron de Montesquieu’s classic work, The Spirit of the Laws, in which he writes, “There is no greater tyranny than that which is perpetrated under the shield of the law and in the name of justice.” 

POSSLEY: I tend to agree with it. I’m not going say that Michael Segal was innocent. That’s not the point of the book. It’s more about the way this was done. It’s about the process. So much of what occurs in the criminal justice system relies on the integrity of the people who are in charge.  Prosecutors are some of the most powerful people in the country. We rely on them to be ethical and honest.

Michael Possley

Maurice Possley

There are people who argue that prosecutors should not be immune from lawsuits and civil liability. Doctors don’t have immunity from malpractice. I think there’s a compelling argument that taking away immunity wouldn’t hurt the ethical prosecutor; it would only potentially expose those who are not ethical. I think most prosecutors are ethical and do the right thing, but I think that they’re in a position to make calls, and sometimes it’s difficult to make the right call, whether it’s because they believe the person is guilty, and the ends justify the means, or whether they don’t want to expose themselves to failure.

Sometimes people are motivated by not wanting to lose, because historically we have judged the success of a prosecutor by what? By his wins. Our system is adversarial, but it doesn’t have to be about winning at all costs. I’ve said this for a long time: the culture has to be changed.

THE CRIME REPORT: What are the roots of Segal’s argument that he was unfairly prosecuted? 

MAURICE POSSLEY: The prosecution thought Michael Segal was someone who could lead them to other people, [because] he was politically connected, a man of significant wealth and power in the city of Chicago.  One day they confronted him in a hotel and said “We want you to wear a wire.” It was clear that they weren’t just after Segal; they were after people they thought Segal could lead them to. This is not an uncommon tactic. It’s used in all sorts of prosecutions.  [Segal refused.]

TCR: You point out in the book that prosecutors who engage in misconduct are more likely to be promoted than punished.

POSSLEY: We have very little accountability for prosecutorial misconduct. When you have a high-profile case, it’s certainly something you want put on your resume. It’s no secret that prosecutors go on to things such as judgeships, elected office, or even white-collar criminal defense work, which tends to be very lucrative. It doesn’t look good if committing misconduct is on your resume.

I was co-author of a study of prosecutorial misconduct that was published about ten years ago in California. The State of California has a law that says if your conduct has been the subject of a reversal, you’re duty bound to report it to the state bar association, But nobody does it, and it’s confidential information, so there’s no way to police it.

book coverI found one case where a case was reversed because the prosecutor was found to have engaged in discriminatory jury selection, excluding minorities, particularly African Americans, and he wrote a letter to the state bar. So I called him up, and I was approaching this as someone who was following the law and self-reporting, and told me, “No, I was telling the state bar that the court got it wrong.” So he was in denial.

Ambition always seems to be involved in some way. We say juries and judges are the gatekeepers, and they perform some gatekeeping functions, but the prosecutor is really the one who has the serious responsibility and to the extent that they can, they should not have their eyes on the horizon; they should have their eyes on what’s directly in front of them.

‘Perfect Storm’

 TCR: Segal seems to make the same point. In the book, he writes, “the prosecutors were free to act with impunity. They knew…that the likelihood that they’d ever be held accountable for their actions was slim to none.”

POSSLEY: This is a conclusion that Segal came to, and a lot of people come to, when they see cases of official misconduct. Even when the courts say this is egregious and we’re going to reverse this case, nothing happens to the prosecutors. There have been worse cases of misconduct—death penalty cases, for example, where prosecutors withhold evidence. That’s pretty egregious. But in terms of this case, it was a perfect storm.

When you look back to the beginning, he was prosecuted for something where there were no victims and there were no losses, and even the judge said there didn’t seem to be a fraudulent intent. What he got prosecuted for was [violating] an insurance regulation that was bootstrapped into a federal prosecution under “honest services, mail fraud and wire fraud,” and then a racketeering conspiracy. He ran an insurance brokerage. There was no testimony that an insurance company didn’t get their premium. There was no testimony that an insurance client never got their insurance. It’s just sort of incredible to me.

 TCR: What role did the media, particularly the Chicago Tribune—where you were a reporter for 25 years—play in the unfolding of the trial?

POSSLEY: I’ll be honest with you, when it was going on I wasn’t paying too much attention to it. The trial was in 2004. I was doing investigative criminal justice stuff, wrongful executions in Texas and things like that. It just didn’t register on my radar.

Looking back at the coverage, you don’t see much coverage of the cross-examination. What coverage you do see leading up to the trial, you don’t see much about pretrial motions.

Why was that? I don’t know, I just know that much of the coverage was negative to Segal and pro-prosecution. The prosecutors usually have the upper hand, they control most of the information, the defense doesn’t necessarily want to publicly fight back.  There’s also a history of journalists in general being pro-prosecution.

TCR: The book lists the epithets thrown at Segal during the closing arguments, including “liar, thief, ruthless, embezzler, crook, fraud artist, tax cheat, schemer.”  It’s always amazed me how lawyers are able to throw terms around like that in the court room without any recourse.

POSSLEY: In my studies of prosecutorial misconduct over the years, one of the most common forms of it is improper argument. It comes down to the fact that these are the closing moments of a case. Pretty soon you can’t control anything because it’s in the hands of the jury. And that’s why you see the worst rhetoric in jury trials. When you’re arguing to a judge, lawyers are savvy enough to now you don’t need to do this sort of thing. So one of the most common forms of misconduct is the improper argument, and this is where in the heat of the moment, all kinds of improper comments are made, and the defense has to make a choice. One lawyer put it this way: “We start objecting to everything and it may make the jury think what we’re trying to do is prevent them from saying it because we think it’s true.” There’s a very fine line to walk.

 TCR: Segal says toward the end of the book, “Despite my experience and the devastating adversity over these years, I still do believe in the Constitution, in the federal system of criminal justice.”

POSSLEY: He’s a resilient guy and he’s been through a lot, and I think that he realizes that there was a period of time where he wasn’t always focused on the right things to the extent that he should have been. I think he was, as you might expect, very driven about his company. He didn’t pay attention to certain details. He’s not been exonerated. He did his time, nearly eight years. He fought and fought. And he did eventually settle his forfeiture. He’s not penniless. I think he’s come out of this with a pretty decent attitude, all things considered.

Additional Reading: “Mindset of Untouchability’ Fuels Prosecutor Misbehavior,” The Crime Report, March 23, 2020

Dane Stallone is a contributing writer to The Crime Report. “Conviction at any Cost” is due out this Spring.

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