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.