Memories, Mobsters, and Motivation--an Interview with Dean Polales

Dean Polales is a Chicago-based criminal defense attorney. After attending the University of Chicago law school, Mr. Polales worked at the United States Attorney's office for over 21 years. He now owns Polales Horton LLP along with his partner, Timothy Horton.

The interview below was conducted in the fall of 2021. It has been edited for length and clarity.

Harvard Undergraduate Law Review (HULR): Why were you initially attracted to becoming a federal prosecutor?

Dean Polales: Well, I wasn't initially. I had always wanted to be a lawyer because my dad was a lawyer, but I thought I'd be a business transaction lawyer. The classes I took at law school were really geared towards corporate law as opposed to litigating and going to court. But then I got a clerkship on the US District Court for the Northern District of Illinois. The judge I worked for, who was a very experienced trial lawyer before he got on the bench, suggested that I sit in the courtroom and watch certain proceedings. And once I saw the criminal cases, and I saw the assistant US attorneys trying cases against very good defense lawyers, it was immediate: I just said, “That’s what I want to do.” 

Aside from the quality of representation, I also came to the realization that prosecutors are able to make sure that justice is done. Prosecutors in federal offices don't just indict and prosecute cases. They review cases presented by the various investigating agencies--the FBI, DEA, IRS, ATF, and so forth--and decline cases that should not be brought. They decide which cases justify the use of judicial and prosecutorial resources and take into account the life circumstances of defendants and any implicit bias in the system.

I was also attracted specifically by the US Attorney's Office in Chicago, which is basically the only game in town for prosecuting corrupt public officials. The state's attorney in Cook County is overwhelmed with common law crimes like murders and burglaries. And while they have an office 10 times the size of the US Attorney's Office in the Northern District, they don't have the investigative resources. Meanwhile, federal prosecutors routinely use the grand jury to investigate cases. They can easily subpoena records and interview witnesses because they have nationwide jurisdiction. So they can reach out and build the case, and determine whether or not there are defenses to the case that the agents by themselves can't do. Right now, for instance, there’s an investigation of the former Speaker of the House in the Illinois legislature, who over the years has enjoyed the reputation of controlling which bills get passed. The investigation is looking into whether or not there was any corruption in some of that decision-making. 

So that’s why I became interested in prosecution during my clerkship. After the clerkship, in the summer of ’81, President Reagan froze all hiring. And so I went off to a big law firm in Chicago looking for trial experience, which is very hard to do as a young associate. Meanwhile, I kept writing to the US Attorney's office every few months asking them to keep my resume on file. And after 19 or 20 months, they called and said, “You won the lottery. Come on in for a series of interviews.” I did, and they hired me. I thought I’d died and gone to heaven.

HULR: What was the first case that you worked on as a federal prosecutor? How did you grow from this experience?

DP: To tell you the truth, I can't remember the first case I worked on--the first year I was there, I think I indicted about 25 cases and wrote 16 appeals. As a newbie, the cases I worked on were mostly reactive rather than investigative cases. For example, there was an ongoing investigation by postal inspectors into theft at a particular post office. There are catwalks in all these places where inspectors can hide and watch the postal workers. They plant test letters and see if the workers will open them. Opening mail addressed to someone else is a serious crime. Postal workers get fired and lose their pensions. At that time, nobody went to jail for a crime like that--they received probation. But the U.S. Attorney’s Office prosecuted a lot of these cases because of the importance of maintaining the integrity of the U. S. Postal system.

I remember another early case, a fraud on a religious organization that ran health care facilities. After investigating it, we indicted it. Ultimately, the fellow pled guilty rather than go to trial, but, of course, that's true in most criminal cases. Those cases are really the earliest ones that spring to mind.

HULR: Over your career, what roles did you play at the DOJ? Which aspects of your job did you most enjoy? What were some of the less enjoyable or the more difficult parts?

DP: I started as what's often referred to as a “line Assistant United States Attorney,” carrying a caseload of more complexity as you become more experienced. When I initially started at the office, there were four divisions, one civil and three criminal. The Criminal Receiving and Appellate divisions did simpler cases and wrote appeals. I then graduated to the Criminal Division, which handled cases of medium complexity across a wider range of crimes. Finally, I went to the Special Prosecutions division, where we mainly focused on public corruption and complex financial crimes.

Special prosecutions would handle cases that involved wiretaps. For example, I worked on a case with maybe 50 different separate wiretaps over a period of two years. The investigation resulted in 120 arrests in various locations in the United States, and the indictment eventually had 320 counts--320 separate crimes had to be proven beyond reasonable doubt--including racketeering and continuing criminal enterprise. It took three months to try before a jury… quite an interesting case. 

After being a prosecutor for three years, I was promoted to a deputy chief of the criminal division. I then moved up to Special Prosecution and then was made a deputy chief in the Criminal Division.. A couple years later, I was made a Deputy Chief of Special Prosecutions and, a couple years after that, the Chief of Special Prosecutions. In my final years, I was Counselor to the United States Attorney--I reviewed complex cases and provided advice to the United States Attorney, who ultimately makes the decisions on all the prosecution. 

What I liked best about my career from beginning to end was being in front of a jury, the show time. The first time I tried a case I made a complete ass of myself. We won the case, but only thanks to the quality of my trial partner, who was ultimately the lead prosecutor in the Oklahoma City bombing case. We became very close friends when he was a line assistant at the US Attorney's Office, and we’ve stayed friends ever since.

That's the other thing about the office: the ethos is, do the right thing. If you didn't feel something was right, you didn't have to do it, no consequences. In other words, “I'm not prosecuting this case. If you want to prosecute it, get somebody else to do it.” Generally, though, that was an extreme case because people avoided bringing a case when there was disagreement. If there was an issue, you would take it all the way up to the front office and have a meeting with one of the management. If you still felt you couldn't do it, it'd be reassigned. That was so rare, though, because the priorities of the office for the most part were serious crimes. 

HULR: What was one case that you worked on that particularly excited or challenged you?

DP: I worked on a racketeering case against Albert Tocco, a mob boss in Chicago who was a lineal descendant of Al Capone’s crew. Chicago has organized crime referred to as “The Outfit.” There are basically three crews in Chicago--the North side, the West side, and the South side crews--that have controlled for many, many years the criminal activity in their respective locations. 

When I arrived at the US Attorney’s office, Albert Tocco ran the south side. Tocco appeared to be a businessman with a waste hauling company worth millions of dollars. In reality, he was the head of the organized crime unit; that enhanced his ability to get contracts from local politicians. Following his prosecution, four or five suburban Chicago area mayors were indicted, because after you chopped off the head of the snake, the people that had been afraid of the fangs realized that they weren't there. And they started flipping and being witnesses for the government. That cleaned up a lot of the south Chicago suburbs that had been corrupt with organized crime. 

The case focused on street tax, which is extortion. If the mob comes to you and says very politely, “I'm here from Albert, where's my envelope,” and you give him $500, it's not because he sold you something--it's because he's going to let you operate in that location without being killed. So if you're running a brothel, for example, you'll pay a tax to the outfit. And if you don't pay the tax, there will be consequences. The south side crew taught everybody those consequences in the Chop Shop wars: guys would steal cars, chop them up, and sell the parts but not pay the tax. So the crew had a whole bunch of them killed, one after the other after the other. Guess what--all the car thieves and chop shop operations started paying the tax. That's how the outfit ran--they used violence and threats of violence up to and including murder to impose discipline on criminal activity, and they extorted street taxes payable to the organization. 

During the racketeering case, we made use of a man in the witness protection program--we’ll call him Doug--who was caught smuggling cocaine from Florida into Chicago’s O'Hare Airport. The DEA thought Doug was just a one-off drug smuggler. In reality, Doug had been a hitman for Tocco’s crew and had committed 14 or so contract murders. Now, there was a rule in the crew that they should not be dealing, so Doug was deathly afraid of having it known that he was being prosecuted for a narcotics transaction off the books.

Meanwhile, Doug helped set up an undercover DEA bust. But the seller, Mario, broke his deal with the undercover DEA agent and tried to shoot him in the head and steal the buy money. Luckily, Mario just missed. Then the DEA agent took his gun out and shot Mario dead.

A couple of days later, Doug called the DEA agent and said, “I have to tell you something, but I need to be promised immunity. There's a hit out on you and your family for killing Mario.” The agent asked, “How do you know?” Doug only replied, “I can't tell you.”

The agent was, understandably, extremely upset and did not go through proper procedures. Instead, he told Doug that anything he said wouldn’t be used against him. The first words out of Doug's mouth were, “I did 14 contract hits for this crew, and they offered this one to me.” 

The DOJ eventually granted Doug immunity; in return, Doug had to go into the grand jury and tell everything he knew in a 250-page, single-spaced, typewritten statement. The DOJ put him in the grand jury and then decided that they were never going to use him because Doug was too bad a guy and had been immunized for 14 hits. 

Well, it's 1989 now and I've got the racketeering case. My trial partner on the case mentioned Doug as a potential witness. I said, “Well, let's go down and meet him.” So I had a neutral site visit--the FBI got us a hotel room in a secret location and stuck me in there with the guy. He seemed to me to be a perfectly usable witness, notwithstanding the fact he'd been immunized for 14 hits. He was very forthright, there was a lot of corroboration for what he said, and he couldn't care less about winning or losing the case. His only concern was keeping his identity secret--he didn't want to get whacked in the town he was working in with a new identity, raising his daughters, and leading a law-abiding life, by the way, because he felt like he was the luckiest guy in the world. 

So we used Doug at the trial. Putting him on was a challenge because the general rule is to front your problems. You disclose credibility problems with your witness, rather than having them come out for the first time on cross examination. I was on the younger side as a prosecutor, and I fronted the 14 murders on direct examination. Later, during the cross examination, an extremely experienced defense lawyer honed in on one of Doug’s crimes. “So you took one of these guys that you hit, and you kidnapped him?” he asked. And the witness, in a very charming Southern accent, just snapped, “Yes, sir.” “Then you drove him off to a forested area on the border of Indiana and Illinois, and you found a motel. And you tied him up in a chair, gagged and bound him, and held him for a week while you were seeing if he would pay the money he owed?” And each of those questions was answered, “Yes, sir.” “And when you concluded that he was not going to be able to pay you what you claim he owed you, you decided to kill him?” “Yes, sir.” “And so you put him in the truck?” “Yes, sir.” “And you took him into the forest?” “Yes, sir.” “You led him out of the truck at gunpoint?” “Yes, sir.” “You walked him into the woods?” “Yes, sir.” “And you untied his hands and handed him a shovel?” “Yes, sir.” “And you told him to dig his own grave?” “Yes, sir.” “And then you shot him?” “Yes, sir.” “Tell me, do you recall whether you shot him in the head or the heart?” And on the witness stand, Doug paused... and yawned. “Excuse me. I believe it was the heart.” At which time the defense lawyer yelled, “Testifying in a federal criminal case is nowhere near as exciting as murder, is it?” “No, sir.”

People in the courtroom were shocked. But, in closing arguments, the fact that he yawned actually enhanced his credibility. Because he yawned, it was apparent that he did not care enough to lie about anything. He had already been immunized, and he was never going to be prosecuted for any misconduct that he had engaged in. So, Doug had every incentive to inform on Tocco. As long as he was telling the truth, he had nothing to lose.

In the end, both Tocco and one of his men were convicted; the boss got 200 years. Now, I had asked for 200 years, which the rest of the prosecution team found outrageous. But at the sentencing, the judge actually excoriated me. The trial evidence alone justified a maximum period of incarceration allowed by law, which was something like 1000 years if you made them all consecutive. Then the judge looked right at me and snarled, “But the government has seen fit to ask for only 200 years. So that will be the sentence.” That was an interesting case.

I also tried another racketeering case against members of the Herrera family. The Herreras were very prominent in Durango, where they owned a lot of land to grow poppy for heroin that was distributed out of Chicago. The case involved over 120 people scattered across the country; we did wiretaps all over the place. It was a neat trial, and everyone got convicted. I think we lost only two counts, which were minor charges against the two least important defendants. 

HULR: What kind of work are you doing now? How does your experience as a federal prosecutor inform that work?

DP: I'm doing a lot of criminal defense work, almost all of which is white collar work. A lot of the work that I do is grand jury work because preventing an indictment is ideal.

My experience definitely informs my current work. I understand in depth federal laws pertaining to evidence as well as the principles of federal prosecution: how prosecutors should behave and what kinds of cases should or shouldn’t be brought. I can speak from a position of some expertise when I'm talking to prosecutors about what they should do. I also encountered many types of crimes over my 21 years. I never stopped taking a caseload no matter what my position was. That experience is invaluable. 

Over the course of time, in Chicago, at least, a lot of the prosecutors, including the last two US Attorneys, have been former colleagues of mine. That doesn't mean they’ll do anything for me, but I know them and I understand what language they speak. We have a similar set of values because of how we grew up in the law. And if I don't think the prosecution is meeting the standards that that office has set over the years, I can talk to the United States attorney or the first assistant. They both have outstanding integrity.

Finally, trial experience helps. The first time I tried a case, I had no idea I was about to be called on by my more experienced trial partner to cross examine a defense witness right out of the box. After I stumbled through an absolutely horrendous cross with no idea what I was doing, I sat down red-faced and wanted to die. But the more you go to the plate and swing the bat, the more likely it is you're going to get better. It doesn’t mean you're going to be Clarence Darrow, but you're going to be a lot better than when you started. Very few people are Athena springing out of the head of Zeus full grown as a trial lawyer, but they can develop those skills.