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Harry Aleman, center, with his attorney, left, as he leaves court after a not guilty verdict in 1977. (Tribune file photo / May 16, 2010)

During the 1970s, just the mention of hit man Harry Aleman’s name was enough to strike fear into those whose doorsteps he happened upon.

“He was the hammer of the Chicago mob,” said Lee Flosi, a former FBI agent who headed the Chicago office’s organized crime section in the 1990s. “You never want him sitting in the back seat of your car.”

But long stretches in federal and state prison and cancer took their toll on the 71-year-old. His state prison mug shot shows a man with sunken eyes, wavy gray hair and a wispy mustache.

On Saturday, Aleman died at Hill Correctional Center in downstate Galesburg. Illinois corrections spokeswoman Sharyn Elman said Aleman had been ill and there were no suspicious circumstances around his death, which happened at about 3:50 p.m., according to the Knox County coroner’s office.

 
Aleman was in prison for the 1972 shotgun slaying of a union official and was suspected in nearly 20 other killings. He was sentenced to serve a term of 100 to 300 years.

The 1997 conviction made American legal history as the first time a criminal defendant had been tried again after an acquittal — the judge had been bought off in his first trial, authorities said. It made local history as the apparent first time in Cook County that a reputed organized crime hit man had been convicted of murder.

Half Italian, Aleman was born in 1939 in the Taylor Street area. By the early 1970s, he had a reputation as an enforcer for various crews in the Outfit, Flosi said. His job was intimidation, and if people engaging in illegal activity neglected to pay the tribute to the local Outfit boss, they would get a visit from Aleman, and just the sight of him was often enough to get people to toe the line.

“He had that kind of fear,” said Flosi, who met Aleman in the 1990s. “He was an intimidating presence.”

Added John Drummond, a retired longtime reporter for WBBM-Ch. 2 who covered Aleman’s trials: “You were in trouble if you looked in your rearview mirror and saw Harry Aleman.”

Aleman gained national notoriety as a cold-blooded executioner, such that whenever authorities came upon unsolved homicides that broadly matched his modus operandi, Aleman’s name would come up.

Flosi said when he was with the FBI in Kansas City, an informant pointed the finger at Aleman for a murder, though agents never built a case against him in that killing. “That’s the kind of reputation he had,” Flosi said.

On the night of Sept. 27, 1972, Teamsters shop steward William Logan was gunned down outside his West Side home as he left for work. Although authorities never established a clear motive for the slaying, Logan was involved in a bitter custody dispute with a relative of Aleman’s.

An accomplice who testified at Aleman’s 1977 trial said he and Aleman trailed Logan for two weeks, then drove to his house that day. The accomplice, Louis Almeida, said that as Logan went to his car, he pulled up and Aleman called out, “Hey Billy” and shot him with two blasts from a 12-gauge shotgun.

Despite the testimony and that of a neighbor who said he saw Aleman at the scene, Aleman was acquitted in a bench trial in 1977 by Judge Frank Wilson. The case was reopened after allegations of a fix surfaced. Wilson committed suicide in 1990 during the probe, and another trial was ordered despite defense objections concerning possible double jeopardy.

At the 1997 retrial, Robert Cooley, a mob lawyer turned government informant, testified he delivered a $10,000 bribe to Wilson to acquit Aleman.

Aleman was convicted the second time. Criminal Courts Judge Michael Toomin sentenced Aleman, who had spent 19 years in federal custody on other charges, to up to 300 years. Officials said Aleman had been suspected in as many as 20 mob-ordered killings, although he was not charged in those cases.

In 2002, the state Prisoner Review Board turned down Aleman for parole. The lone board member who voted in favor of letting Aleman out later was charged with — but later cleared of — trading his vote for help in getting his son a gig as an entertainer in Las Vegas.

Flosi, now the owner of a private security firm, said he met Aleman in the early ’90s, when his office gathered evidence that eventually led to the hit man’s second murder trial.

“He was very cold, very calm, the kind of guy you couldn’t get excited. He wasn’t going to be intimidated by the badge,” Flosi said. “He was a ruthless guy, no doubt about it.”

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