CHICAGO -- At first blush, the criminal cases against Jussie Smollett and Harry "The Hook" Aleman would seem to have little in common.
One involves a minor celebrity who gained international notoriety for allegedly staging a hoax hate crime on himself. The other was a shadowy Outfit enforcer who twice stood trial for the 1972 gangland slaying of a union steward.
But even though Aleman's decidedly more serious case unfolded decades -- and worlds -- apart from Smollett's, it now provides an intriguing look at the legal pathway prosecutors might use to block Smollett's attempts to get the new charges against him thrown out of court on double-jeopardy grounds.
And linked to both cases is the same Cook County judge -- Michael Toomin.
In 1997, Aleman became the first defendant in U.S. history to be retried on murder charges after having been acquitted at trial. In a landmark decision, Toomin ruled that the Constitution's double-jeopardy protections didn't apply to Aleman because the original judge had been bribed.
Fast-forward 23 years, where there promises to be a legal fight over whether new disorderly conduct charges filed against the actor Tuesday violate those same double-jeopardy protections. Lawyers for Smollett are expected to argue the new charges represent prosecutors unfairly taking another bite of the apple, as the actor first was charged last year in a case that eventually was dropped amid controversy.
But legal experts told the Tribune that defense argument is likely to fail, and point to Aleman's case as Exhibit A.
In ordering a special prosecutor in the Smollett case last summer, Toomin echoed what he'd said in the Aleman case, ruling that since State's Attorney Kim Foxx had not properly recused herself from the investigation, the entire case was essentially invalid from start to finish. Prosecutors could use the ruling to argue there was never any real legal jeopardy for Smollett in the first place.
"That first (Aleman) trial was a sham trial because he really wasn't in jeopardy, the case was fixed," said K.S. Galhotra, a former supervisor in the Cook County public defender's office now in private practice. "This is sort of along those lines ... because Judge Toomin said it was a void prosecution, the case can begin anew."
Aleman was one of the Chicago Outfit's most feared hit men, a ruthless enforcer who could bring a wayward gambler or anyone else who'd run afoul of the mob back in line with one hard stare from his notoriously coal-black eyes.
Nicknamed "The Hook" for his mean left fist while growing up in Chicago's Taylor Street neighborhood, Aleman was suspected in brazen executions of victims sitting in front of their homes, stepping out of cars, or dining in restaurants with their family. Others were found blindfolded and tortured, stuffed in car trunks, stabbed in the neck with a broken mop handle.
But it was the Sept. 27, 1972, shotgun slaying of Teamsters dockworker William Logan that eventually brought Aleman down -- and made legal history. It was the first criminal case in the country where a defendant who was initially acquitted was retried on the same charge, a move that seemingly violated the long-held legal principle against double jeopardy.
Aleman's first murder trial ended in acquittal in 1977, when Cook County Circuit Judge Frank Wilson cleared him in a bench trial despite testimony from Aleman's friend and alleged accomplice, Louis Almeida.
More than a decade later, crooked mob attorney Robert Cooley, who had begun cooperating with federal investigators as part of a sweeping undercover probe dubbed Operation Gambat, admitted he delivered the $10,000 payment to Wilson.
When Aleman was recharged in Logan's murder in 1993, prosecutors knew they were in for a legal fight over whether they had violated double-jeopardy protections. The case landed before Toomin, at the time a circuit judge sitting at the 26th and California courthouse.
In 1994, in what was hailed as a first-in-the nation ruling, Toomin held that the bribe paid to Wilson had so fundamentally tainted the first trial that it could be considered a "sham," invalidating any double-jeopardy protections afforded to Aleman. Toomin said he'd researched the issue going back centuries but could not turn up a single case offering any legal precedent.
Aleman was convicted by a jury at the retrial in 1997 and sentenced by Toomin to serve up to 300 years in prison. He died in 2010 at age 71, while serving out his sentence in a downstate prison.
Smollett's legal challenges
A special Cook County grand jury on Tuesday indicted Smollett on six counts of disorderly conduct alleging he orchestrated a racist and homophobic attack on a frigid night in downtown Chicago in January 2019.
The allegations were nearly identical to charges brought -- and then mysteriously dropped -- by Foxx's office last year. Foxx had recused herself from overseeing the prosecution, revealing she'd had contact with a member of Smollett's family early in the investigation at the request of Tina Tchen, Michelle Obama's former chief of staff.
But in appointing attorney Dan Webb as special prosecutor last year, Toomin wrote that Foxx botched the recusal by handing the reins to her top deputy. Because the recusal was invalid, the entire process played out without a real prosecutor at the helm, he wrote.
"Discerning members of the public have come to realize that the 'recusal that really wasn't' was purely an exercise in sophistry," Toomin wrote.
The ruling was reminiscent of his decision in the Aleman case because it essentially invalidated the entire prosecution. Legal experts said the similarities may be the strongest shield prosecutors have against any attempts to get Smollett's new case thrown out.
"Toomin wrote a brilliant opinion in Aleman," veteran defense attorney Richard Kling said. "It ... came to the conclusion, no jeopardy, no double jeopardy."
The experts did raise a few possible avenues for Smollett's attorneys to challenge the new indictment -- but all of them likely would be long shots even without Toomin's finding, they said.
Smollett's attorneys hinted months ago that any new charges would violate his double-jeopardy protections. But those only kick in once a guilty plea has been entered or a trial has begun, experts said.
Alternately, Smollett's attorneys could argue that last year's agreement to drop charges counts as a binding contract, similar to a formal plea, Kling said. New charges would violate that agreement.
Or the defense could try to throw out the case based on the legal principle that prosecutors cannot bring new charges based on the same alleged incident without potentially violating the defendant's right to a speedy trial.
But that may not be successful either, experts said, since the first case was dropped altogether and a new set of prosecutors is starting over completely.
"There's a lot of angles (the defense) can play, I just don't think any of them are going to pan out," Galhotra said.
Smollett is scheduled to be arraigned Feb. 24 at the Leighton Criminal Court Building.
Meanwhile, his attorneys have steadfastly maintained his innocence, and last year rebuffed attempts to negotiate a formal plea. If they couldn't get a full dismissal, they told the Tribune last year, they would take the case all the way to trial.
If they maintain that position, both sides are in for an extensive fight over the actual evidence. And Smollett's attorneys have already laid out much of their case in public, largely by attacking the credibility and motivations of two key prosecution witnesses, brothers Abimbola and Olabinjo Osundairo.
The brothers told police and a grand jury that Smollett paid them to stage the attack.
The actor's attorneys have argued in previous filings that the brothers' story was just a frame-up to avoid culpability for their actual attack on Smollett.
But those arguments will only play out in a courtroom if the defense fails in its attempts to toss out the new case altogether. And as the Aleman case showed, claiming a double-jeopardy violation likely won't do the trick.
After Toomin's ruling in 1994, then-Cook County State's Attorney Jack O'Malley said double-jeopardy was "amongst the most recognized, yet most commonly misunderstood, doctrines in our law."
"Everyone thinks they know what double jeopardy is, and very few people do," he said.
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