Harry Aleman was born on January 19, 1939, in the Taylor Street neighborhood of Chicago — a historic hub for Italian-American immigrants. He was the eldest of three sons born to Louis Aleman, a Mexican national reportedly involved in narcotics trafficking, and Mary Virginia Baratta, an Italian-American. His family connections ran deep in the underworld: he was the nephew of future Outfit acting boss Joseph Ferriola.

Harry’s childhood was marred by violence. In a 1997 interview, he revealed that his father beat him daily — a pattern only interrupted between ages seven and eleven, when his father was incarcerated. Despite the abusive home life, Aleman showed early signs of discipline in more constructive pursuits. He graduated from Crane Technical High School in 1956 and enrolled in the Chicago Academy of Fine Arts, earning a two-year commercial art degree in 1958.

Following his graduation, he worked mundane jobs — selling race track programs and produce in Chicago’s markets. In 1964, he married Ruth Felper Mustari, a widow with four children. Due to a teenage accident, Aleman was unable to father children of his own, but was reportedly a devoted stepfather and loving husband, according to family members.

Harry Aleman became a prominent enforcer for the Chicago Outfit during the 1970s, feared throughout the city for his ruthlessness and efficiency. Law enforcement and the Chicago Crime Commission suspected him of involvement in at least 13 murders between 1971 and 1976. His targets included mob informants, rogue bookmakers, a museum guard with gambling debts, and even other Outfit enforcers. FBI agents claimed that Aleman “oozed menace,” and that often, his mere presence was enough to ensure compliance.

His most notorious crime was the 1972 murder of Teamsters official William Logan. On September 27, 1972, Aleman ambushed and fatally shot Logan near his home. Prosecutors believed Logan’s obstruction of Outfit hijacking operations was the motive. However, it later emerged that Logan had been married to Aleman’s cousin, and a bitter divorce involving child custody disputes may have provoked the hit. According to informants, Logan had physically abused his ex-wife, and Aleman was incensed by racial slurs the victim allegedly used against him.

Though two witnesses saw Aleman commit the murder, the initial 1977 bench trial ended in a stunning acquittal. This result, however, was later revealed to be the product of organized corruption. Chicago attorney Robert Cooley, who had been approached by political fixer Pat Marcy, was pressured to hand the case to a bribed judge — Frank J. Wilson. Despite having a winnable case, Cooley secured the bribe, and Wilson accepted it. Aleman was freed.

This acquittal eventually collapsed under the weight of Operation Gambat, a massive federal probe into corruption in the Chicago courts. Fearing indictment, Judge Wilson committed suicide in 1990. Aleman, meanwhile, had served a 30-year sentence beginning in 1978 under RICO laws for a string of home invasions. He was paroled in 1989 but re-arrested in 1991 for extortion.

In 1993, prosecutors finally moved to retry Aleman for the Logan murder, arguing that the first trial had been a fraud and never legally placed him in jeopardy. The courts agreed — ruling that since the judge had accepted a bribe, jeopardy had never attached. Therefore, retrying Aleman did not violate the Fifth Amendment’s double jeopardy clause.

On October 31, 1997, Aleman was convicted of Logan’s murder and sentenced to 300 years in state prison. His case remains a landmark in American legal history — the only known instance where a person was retried for murder after an acquittal, due to judicial corruption voiding the first trial.

Harry Aleman died on May 15, 2010, from complications of lung cancer while incarcerated at Hill Correctional Center in Galesburg, Illinois. He was 71 years old. He was buried in Waldheim Cemetery in Forest Park, Illinois.