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Hitman Harry the Hook and the Crooked Cook County Judge: Another Lesson in Judicial Corruption [1]
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Date: 2023-11-05
Now we find out that Clarence Thomas didn’t actually pay for that plush RV of his. What’s next? The Chief Justice’s wife didn’t actually earn those million dollar finder’s fees? Justice Alito didn’t really catch that huge King Salmon? Brett Kavanaugh doesn’t really like beer? Oh, the humanity!
Some time ago I posted an article [here] on the current crisis of corruption in the Supreme Court and how it must necessarily impact the efficacy of the Court’s output of decisions, not just today’s but also from the past, and even more so looking into the future. Towards the end of the piece I mention, in passing and by way of comparison, the judicial scandal that rocked the Cook County, Illinois courts system in the 1980s and ‘90s, centered around the FBI’s Operation Greylord and related investigations. As scandals go it was a nasty one, full of dirty money, dirtier black robes, sleezy lawyers, and plenty of other low-life villains.[i] When the extent of the corruption was finally exposed, things were a mess in Chicago and the surrounding suburbs, judiciary-wise, and it remained that way for many years.
It was a reckoning, or so I argued; the kind of reckoning that we as a nation must inevitably face today except on a far greater and more impactful scale, since this time it is the highest court in the land doing the bad stuff. Certainly there are differences between the two, the Cook County scandal back then versus the D.C. nine today: no secret sophisticated real estate deals, no PAC-to-PAC dark money wire transfers, and no all-expenses-paid luxury vacations in the earlier Chicago version; picture more like smoky chambers, side-eyed courtroom nods, and bundles of soiled cash handed off in bathrooms. Still, the parallels between the two are inescapable. As are the lessons to be learned from them.
The mere musings of a cranky old ex-lawyer, perhaps; but one who has witnessed, over the past several decades, in both high court and the low, what can happen when the arc of justice gets bent towards mendacity and greed. However and whenever the current crisis finds resolution—when Mrs. Roberts lands her last big fee, Samuel Alito lands his last big fish, and Clarence and Ginny are forced to actually shop at Walmart—at the end of the day, judicially speaking, the impact of their conduct will scar the entirety of our federal judicial system deeply, and it will take a long time for it to recover. As with Greylord , things will be a mess for quite a while.
Thus, now is a good moment to revisit the Greylord era, for a telling of the tale of Hitman Harry the Hook[ii]. The local corruption ran deep and dark in the Cook County courts back then, especially at the Criminal Courts complex at 26th and California on Chicago’s South Side. This particular episode finds its home there, and it has everything: murder and greed, betrayal and retribution; justice denied because the fix was in, but justice which ultimately prevailed. And reckoning, lots of reckoning. I turn to the opening sentence of the U.S Seventh Circuit Court of Appeals’ opinion in the case of Aleman v. The Honorable Judges of the Circuit Court of Cook County, etc.,[iii] which neatly summarizes the core of the story:
“Harry Aleman successfully bribed a Cook County Circuit Judge to acquit him of a murder charge in a 1977 bench trial.”
Harry Aleman was born in 1939 in the Taylor Street neighborhood on Chicago’s West Side. He was a promising student in high school, and in 1958 he graduated from the Chicago Academy of Fine Arts with a degree in commercial art. That was not to be his calling, however. Soon Harry, a nephew of Chicago mob boss Joseph Ferriola, was a hard-working foot soldier in the Chicago Outfit. By the 1970s he was its most feared enforcer and a ruthless assassin. Though his weapon of choice was the shotgun, Harry was also good with a handgun, and he was deadly with his fists; they called him “the Hook,” because of his boxing style from when he was a young man. Harry preferred to practice his kind of art up close and personal, it seems.
In September of 1972 Harry Aleman shot William Logan up close and personal, twice with a shotgun and once with a pistol, as Logan, a Teamsters Union official, stepped outside of his family home in Chicago on his way to work. While it remains unclear whether the hit was business-related or not (Logan, besides being involved in some union shenanigans, was formerly married to the sister of one of Harry’s friends, and he had beat her up, beat up the brother, and threatened to beat up Harry), what was undeniably evident in the aftermath was that Mr. Logan was dead and there were two live eyewitnesses: the driver of the getaway car (later identified as Louis Almeida), and Bobby Lowe, a neighbor out walking his dog at the time. Although Lowe at first denied seeing anything, he eventually admitted to the Chicago police investigating the case that he’d been standing just a few feet away from Harry when the final shot was delivered. He even picked him out of a photo lineup, easily. The police file on the investigation soon mysteriously got buried, however. And so Harry Aleman remained on the street. And the bodies piled up.
Then in 1975 Louis Almeida, the getaway driver, who by then was on the run for fear that Harry Aleman intended to do him next, was pulled over by the Ohio State Police and arrested on a weapons charge. Louis quickly cut a deal and he sang like a caged high tenor, including giving up Harry Aleman on the Logan hit from three years earlier. Almeida and the information made their way from Ohio back to Chicago, where prosecutors dug up the old case file (found right where the cops had buried it), dusted off the evidence, and tracked down the other witness, Bobby Lowe. Pulling it all together, they were soon crowing that it was the best hitman case anyone had ever seen. In early 1976, for the first time in his career, the infamous Harry the Hook was charged with murder.
But Harry knew the Cook County courts system. On this particular journey of his towards justice, he hired a crooked lawyer, Thomas J. Maloney, who hooked up with another crooked lawyer, renowned South Side mob fixer Robert Cooley, and together they manipulated the assignment of the case to get it before the Honorable Frank J. Wilson, a crooked judge. After waiving jury and going through a four-day bench trial, Harry Aleman was found not guilty. “Reasonable doubt,” Judge Wilson explained at the close of the evidence; you know, credibility of the witnesses and such. What the Judge failed to mention was that he had accepted a $10,000 offer to fix the case. When Robert Cooley delivered the final payment to him—a bundle of soiled cash handed off to his honor in the bathroom of a downtown Chicago restaurant—Judge Wilson expressed his deepest regrets: not that he had taken a bribe or corrupted the system or let a notorious murderer walk free, mind you, but that he had done so for only ten grand.
And the bodies piled up.
But not for long. By that time the FBI was building a RICO case against Harry and several of his cohorts on a series of burglaries and home invasions that they had committed over time in the ordinary course of their business. In 1978 Harry was convicted in that case, and he was sentenced to Fed time, eleven years. Shortly after he got out, in 1990, they then got him on another RICO charge, and he went back in for another eight.
During Harry’s time inside, Operation Greylord and its offshoot investigations were conceived and carried out and the results revealed to an incredulous public. Lots of heads—judges, lawyers, clerks, cops, even a State Legislator—went on the chopping block from 1983 until well into the ‘90s, for all kinds of judiciary-related crimes. One of the featured defendants was none other than Thomas J. Maloney, Aleman’s original lawyer in the 1977 murder case. Maloney had managed to get himself appointed to the bench soon after he helped get Harry off, and from then until his retirement in 1990 he doled out his own special brand of crooked justice at the 26th and California complex. In 1991 the feds indicted him for taking bribes in several cases, including a few murders. He was eventually convicted and sentenced to 15 years. When he died, in 2008, one of his obituaries described him as the most corrupt judge in U.S. history (A first-place honorarium that might someday soon be subject to challenge).
One of the people who testified against Judge Maloney at his trial was none other than his old pal from the Aleman case, the lawyer/fixer Robert Cooley. Both Cooley and the Aleman judge, Frank J. Wilson, had somehow managed to dodge scrutiny in the first wave of Greylord accusations. But Cooley was about to have an epiphany; and it really was his conscience, he insisted—never mind that he was broke, the feds were closing in, and he owed some seriously overdue gambling debts to some seriously ill-tempered mobsters. In any event, in 1988 he marched into the FBI’s offices and did the caged high tenor thing, singing out on a lifetime of fixing court cases, including the 1977 Aleman murder trial.[iv]
Which was why, in February of 1990, by which time Robert Cooley was a full-time FBI undercover informant and Judge Frank J. Wilson had retired from the bench and was living in Arizona, Cooley went down there to visit him. It was right before Wilson’s indictment was supposed to be announced, and Cooley was wearing a wire, hoping to elicit some admissions from the judge as to past crimes. But the wily old jurist remained coy, and he gave away nothing. The next day, as Cooley headed back up north, Judge Frank J. Wilson headed out into his back yard in the Arizona desert—his deepest regrets at that point in his life unspoken and therefore unknown—and he blew his brains out.
And here’s where it gets really interesting (from a lawyer’s perspective, anyway): Knowing that the first trial had been fixed and with Cooley’s testimony able to prove it, in 1993 the State of Illinois indicted Harry Aleman for the second time for the murder of William Logan. Harry’s new lawyers screamed double jeopardy, of course. But the state argued that there had been no real jeopardy in the first case, since Harry’s not guilty was bought and paid for, and therefore there was no double jeopardy in the second one. And the courts agreed. Harry was convicted, and he was sentenced to 300 years in prison (where he died in 2010). It was the first case in U.S. history in which the Fifth Amendment’s double jeopardy protection was ruled inapplicable where the defendant, having first been found not guilty after fixing the case, was later tried and convicted on the same charge. That ruling survived Harry’s numerous appeals, culminating in the 7th Circuit’s 1998 ruling cited at the beginning of this article. Notably, the Supreme Court declined to review that case.
So, in essence the Aleman court ruled that if an accused bribes a corrupt judge to get a not guilty, the state gets another whack at him. But what about when the accused doesn’t bribe the corrupt judge, and instead he’s the one who gets whacked? In the only Greylord -related matter to make it all the way up to the U.S. Supreme Court, in the 1997 case of Bracy v. Gramley,[v] Justice William Renquist, writing for a unanimous Court (irony note here: including Justice Clarence Thomas) held that the defense side is entitled to some relief from judicial corruption as well. The defendant in that case, William Bracy, had been tried and convicted on a murder in Chicago, and the judge had sentenced him to death. A few years later, while Bracy was on death row, an Operation Greylord offshoot revealed that the un-bribed judge in his case was not only a bribe-taker, but that he also had a reputation for bringing the hammer down on those who did not pay him. The judge’s name? Thomas J. Maloney. The Supreme Court’s ruling effectively acknowledged that, at least sometimes, the mere possibility of corruption can be enough to cast doubt on a judge’s decisions.
As I pointed out in my earlier article, I am a big fan of judicial dissenters. In a footnote at the end of Justice Renquist’s opinion in Bracy, he cites with approval the powerful dissent of Judge Ilana Rovner in the lower 7th Circuit Court of Appeals’ overturned ruling in the same case[vi]. Judge Rovner did nothing to cloak her contempt for Judge Maloney in what she wrote (the classic quote: “Maloney was a criminal who, as a judge, transformed his very office into a racketeering enterprise.”). She also cited several important and long-established principles of law that can and should be applied to any judicial scandal, high court or low. Among them:
“The quality of justice we can claim to have achieved in this nation is not measured by what our best judges do, but by what the worst of our judges have done.”
In the end, the decisions in Bracy and Aleman did not have a huge impact on the post- Greylord cleanup efforts back in Cook County. But by then the local reckoning—the mess—had already gotten well underway on its own, with hundreds of old cases brought back to the musty, dark-paneled courtrooms of 26th and California, there to be examined closely for evidence of the taint of corruption. Some of them ended up being retried, and some got tossed, though most were allowed to stand: a subtle reminder of the presumption of correctness that the law bestows upon all things done judicially.
But the biggest damage was to the Court’s reputation, and to the public’s confidence in the system itself. In some ways that aspect of the scandal still lingers there on the South Side, even now, forty-some years later. Follow the crowds into the main building at 26th and California on any Monday morning, and you can almost smell it in the woodwork: remnants of the stench of Greylord .
Another great citation by Judge Rovner in her dissent in Bracy :
“To perform its high function in the best way, justice must satisfy the appearance of justice.”
That’s a powerful notion. And it’s true. After all, the efficacy of any judicial system lies not in the power of the court to impose its rulings on the public, but in the willingness of the public to accept them as being fair and just, and to trust in the wisdom and integrity of the ones making them.
The appearance of justice. As a young lawyer I sometimes visited the South Side venue, and I recall that I didn’t like it one bit: the feeling of being prey, and of being subject, both myself and my client, to the whims of corruption. Sometimes I imagined myself as a party to an old case, be it civil or criminal, and I thought of how it would have weighed on me, knowing that the judge deciding my fate had his hand out; or worse, not knowing it. Then I imagined myself as an ordinary citizen, a member of the public, and I wondered how it must have felt back in the days of Harry the Hook, after learning that a corrupt judge had let that vicious murderer walk free in my community. Hell, I was that citizen.
And now I imagine myself as a litigant in an important lawsuit, a big one that has made it all the way up to the Supreme Court. At that point I, and no doubt others, are heavily invested in the outcome of the case, whether financially, personally, or otherwise. The attorneys for our side have assured us of the soundness of our position, based on the strength of precedent and established law. They foresee a positive outcome, they tell us. But then we lose. Whether the decision was 5-4 or 9-0 really doesn’t matter, nor does the why; we are in shock, all of us, including the lawyers and everyone else who supported our cause. But that’s it. Because there is no higher authority than the Supreme Court. So the case is done. Then a few years later I learn in the press that the Chief Justice’s wife had been paid millions of dollars in “finder’s fees” by the law firm representing the other side. And they didn’t tell anyone about it. Nobody did. They kept it a secret. How’s that for satisfying the appearance of justice?
Still, I am left with the nagging notion that the two scandals, Greylord from the twentieth century versus the High Court scandal of today, cannot be so readily compared. Though each evidences a deep corruption at the institutional level, my misgivings whisper that the two simply cannot be equated, ergo nor can the lessons learned from them, nor their consequences. Admittedly the payoffs in each differ drastically, in both amount and species, as well as the methods of delivery. And there’s a world of difference in the vacations they took. Perhaps it’s just the imagery that’s bothering me. Or maybe the smell. Lowlife sleaze on the one hand, suave sophisticated chicanery on the other: each gives off its own distinct aroma.
A friend of mine from high school days, a Chicago kid who, like me, went on to college and law school, spent the early years of his legal career much closer to our South Side roots than I did, so he experienced Greylord up a lot closer. I asked him about it, about this comparison I was trying to make, drawing parallel lines of corruption between then and now.
“Picture it,” I said to him. “Over there you have Judge Frank J. Wilson, who is standing in a restaurant bathroom holding Robert Cooley’s envelope full of soiled cash, the final payoff for letting Harry the Hook off on that murder charge. The Judge lifts the envelope high, and with a scowl on his face he says, ‘Is this all I get?’
“Then over here you have Supreme Court Justice Samuel Alito. He’s standing on a riverbank in Alaska, lifting high a huge King Salmon and smiling like it’s everything he ever wanted. He caught it while on an all-expenses-paid luxury vacation compliments of his new billionaire buddy, who is also there smiling like he’s hooked exactly what he wanted.”
I said to my friend, “I see these two as representing the same thing. As if, evil-wise, there is not a hair’s breadth of distance between them. But then I hesitate. Why? What is the difference?”
My friend thought about it for a while. Then he said, “The fish. That’s it, man, just the fish.”
[END]
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