Eddie O'Hare circa 1938

Edward Joseph O'Hare (1899-1939): Capone Front Man; War Hero's Father

By Gustavo Azevedo and Homer Johnson

The O’Hare family name is known worldwide as Chicago’s famed O’Hare International Airport. Construction began in 1945 and in 1949, the new airport was named after Lieutenant Commander Edward Henry “Butch” O’Hare, a World War II naval aviation hero.[1]

Butch never lived in Rogers Park, and neither did his father, Edward Joseph (Eddie) O’Hare. 

But in 1939, the Chicago Tribune reported discovery of an apartment in the basement of 1220 West Sherwin Avenue. Eddie O’Hare owned the $100,000 building where the basement apartment was expensively furnished with period furniture, oil paintings and bronze vases. The carpeting was covered with expensive rugs. Venetian blinds covered the windows, and there was no bell to ring the apartment from the front door. It had a telephone, but the number was not listed in the telephone directory.[2]

The Tribune reported that the luxurious hideout was kept for whenever Eddie O’Hare felt the need to disappear for a while — because O’Hare was an attorney known in 1930s Chicago as the “millionaire front man for the Capone gang syndicate.” [3]

Eddie O'Hare and Scarface Al

O’Hare was a shady character from St. Louis, Missouri, who dabbled in several business ventures, including both dog and horse racing. In 1927 he divorced Selma O’Hare, Butch’s mother, and headed for Chicago. He quickly made friends with Al Capone, and around 1928, O’Hare and Capone joined forces in several racetrack ventures. Although no evidence was found that Capone was an “official” business partner, O’Hare was infamous as the businessman investing Capone’s funds in legitimate businesses. At the time, Capone and his gang were the most notorious criminals in the United States.

In 1925, Johnny Torrio was the leader of the former “Diamond Jim” Colosimo mob when he was severely wounded in an attempt on his life and decided to retire, giving the leadership to his right hand, Al Capone.[4]

At the time of Capone’s rise, there were three sides of crime in Chicago.

The first is racketeering, a set of illegal actions that generate crime-based income disguised as legitimate business profits. Racketeering can include fraud, extortion, bribery and other illegal activities.[5]  Capone’s men typically used extortion to force individuals or businesses pay a “tax” for protection or simply to be left alone by the gangsters.

The second side resides in a novel law of 1920s America. Prohibition criminalized the production, distribution, and consumption of alcoholic beverages, but demand for liquor and beer was still strong in Chicago and other cities. Capone sought to coordinate, import, and sell liquor, and his organized crime network made millions bootlegging.[6]

The third side of organized crime was gambling.[7] Capone’s third stream of revenue came from unlicensed, secret casinos and the seemingly legitimate racetracks operated by Eddie J. O’Hare.

Chicago Tribune, May 27, 1927

O’Hare’s education, intellect, and “suavity” allowed Capone’s gang to move away from the bloody mess of Prohibition and into areas they had never before considered.[8] A “clean” stream of money was precious to Capone then. And just like that, O’Hare became vital to most of Capone’s dealings.

O’Hare had business partners and friends everywhere, especially among state legislators and judges. Municipal Judge Eugene J. Holland was investigated once it was found he had business ties with O’Hare. The two were part of a realty group that purchased land on the south side of Chicago.

In a statement released to clear his reputation, Holland said of O’Hare: “I have never heard of him being associated with hoodlums or racketeers. In fact, he was outspoken in his condemnation of them.”
Perhaps coincidently—but most likely not—Judge Holland was also under fire for releasing more than seven hundred accused bookies and gamblers a month. Many believed he was on the mob’s payroll. [9]

Racing Dogs

O’Hare was the first to bring dog racing to Chicago and perhaps the first to introduce it to the local criminal underworld.[10] He partnered with Al Capone in a horse track at Sportsman’s Park, a dog track called Hawthorne, and other racing ventures outside Chicago.[11] Capone was a mysterious crime boss with an elusive nature in those early days. Newspaper articles would call him “Caponi,” “Al Brown,” or “Scarface.” But even with the lack of information, most could smell something fishy around those racetracks.

In 1927, gambling venues were limited by law to taking only 10% of bets made as earnings. Still, the venues operated by the International Greyhound Association (said to consist mainly of members of Capone’s mob) always found a way around that limitation. At their Hawthorne track, they were not only in charge of concessions, ticketing, and form chart sales but were often handed “tips” in envelopes.[12]

Sportsman’s Park, located on Cicero, was one of O’Hare’s (and subsequently Capone’s) most profitable businesses. Capone was infamous for feeding hamburgers to all the Sportsman’s Park dogs except the one he wanted to win.[13]

Chicago Tribune, May 6, 1927

Al Gets Locked Up; Eddie Gets Richer

In 1930, the IRS built a case against Capone to prove he received a considerable income (based on his spending) but paid no income tax. On November 24, 1931, Capone was sentenced to eleven years in federal prison for tax evasion. He served some of his sentence in Atlanta Federal Penitentiary and the remainder in Alcatraz, California.

Capone wasn’t the only one in the gang to go down. His brother Ralph “Bottles” Capone, Jake “Greasy Thumb” Guzik, Frank Nitti, and others were subject to tax evasion charges.[14] O’Hare, on the other hand, was not charged and never went to prison.

During Capone’s incarceration, O’Hare’s wealth continued to grow. In 1937 and 1938, the O’Hare family had 3,875 of the 10,000 shares of Sportsman’s Park. Eddie had 3,490 shares, Butch had 129, and Patricia and Marilyn (Eddie’s two daughters) had 128 each. At $13.68 a share, the family earned $53,010 in those two years combined.[15] This profit would be equal to $1,121,684 today.[16]

During Capone’s absence, O’Hare grew in paranoia just as much as in wealth. Reports from two convicts  recently released from Alcatraz fed into O’Hare’s fear. Word passed down  through friends that Capone was making constant threats against “Eddie.”

To prepare for any harm that might come to him, O’Hare made provisions for his future. He organized a large trust fund for his children, a $96,000 life insurance policy (more than $2,000,000 today) [17] and set up the Rogers Park apartment in case he needed to hide out.

During a 1939 questioning session, William Johnstone, Sportsman’s Park’s publicist, described a memorable image of O’Hare cleaning and oiling a pistol before leaving the track.

“I never had seen him with a gun before. But it wasn’t any of my business,” Johnstone said. “My business is publicity–not guns.”

Slain

Thirty minutes later, Eddie O’Hare was murdered.[18]

On the night of November 8, 1939, while driving down Ogden Avenue at Rockwell Street, O’Hare was ambushed by assassins armed with shotguns. He was hit with one shot to the neck and another to the head. He lost control of his coupe and went over the curb, colliding with a light pole.[19]

Detectives were immediately on the case. O’Hare was high up in Capone’s ranks, and his death meant a sudden and inevitable shift in Chicago’s criminal underworld.

The investigators quickly surmised that Capone must have been responsible for the deadly ambush. As O’Hare coordinated much of Capone’s cash, no other mob would dare harm him. An unsanctioned hit on Capone’s front man would have led to a gang war, and no other gang wanted a feud with Capone’s forces.

Next, investigators looked at possible motives for targeting O’Hare in such a violent manner. They reasoned three possibilities at the time. First, O’Hare was rumored to have rejected a generous cash donation to Capone’s family during his incarceration, a symbolic gesture of respect. The second was Capone’s envy of O’Hare’s increasing wealth from running mob-owned enterprises. Lastly, Capone’s fear that O’Hare could take control in his absence could have been a motive.

One line of investigation was a search O’Hare’s properties, which revealed the secret hideout at 1220 Sherwin Avenue. The apartment had no nameplate or bell. The front door contained two locks. The windows were covered with light-tight shades so that no one could see in. The investigators surmised that O’Hare went to the apartment when he needed to drop out of sight temporarily. Neighbors reported that he always had a couple of men with him when he entered the apartment.

Inside, investigators found numerous papers and letters, some valuable in tracing O’Hare’s business and personal affairs. Thousands in cash and two checking accounts in O’Hare’s name, totaling the equivalent of about $920,000 today were also found.[20]

Who Was Eddie O'Hare, Really?

In 1947, nearly a decade after O’Hare’s death, Frank J. Wilson, former chief of the United States Secret Service, stated in an interview that “On the inside of the [Capone] gang, I had one of the best undercover men I have ever known: Eddie O’Hare.”

The story that O’Hare suddenly discovered that Capone was doing something shady in 1930 and turned him into the IRS does not hold water. He probably aided the investigation to save his skin. Allegedly, O’Hare struck a deal to avoid prosecution and became a secret witness for the IRS, giving them the information that helped convict Capone in 1931.[21] The conviction made Wilson’s career. He spearheaded the plan to charge Capone with tax evasion and, in 1936, was promoted from Forensic Accountant to Chief of the U.S. Secret Service.[22]

Wilson’s revelation became the most likely reason for O’Hare’s assassination. Capone found out he was working with the IRS and had a part in his conviction.

Wilson stated that O’Hare’s help went beyond feeding ledgers to the IRS. He also warned Wilson that there was a $25,000 reward on his head and $50,000 for the murder of two key witnesses. When the rewards did not lead to casualties, Capone hired assassins to deal with his issues. Wilson said O’Hare told him of Capone’s plan.

“The big fellow [Capone] is going to get you. They know where you keep your automobile. What time you get in at night and what time you leave in the morning,” Wilson quoted O’Hare. “The big fellow has brought in four killers from New York to do the job. You’ve got to get out of there, Frank.”[23]

Butch "Ace" O'Hare Redeems the Family Name

Lt. Commander Edward H. "Butch" O;Hare, USN
Butch O'Hare and his wife Rita meet President Franklin Roosevelt at ceremony awarding him the Medal of Honor

Whether Eddie O’Hare was a hero or not, his son, Edward Henry “Butch” O’Hare certainly was. He demonstrated terrific courage in the air battles of World War II. In February 1942, Butch was a fighter pilot aboard a Navy carrier. When nine Japanese bombers suddenly appeared on the horizon, the first group of American fighter pilots went up to intercept them. In the group’s tail, Butch and his wingman were the only ones to see a second group of bombers incoming. As the next nine Japanese bombers approached, the wingman’s guns jammed, leaving Butch all alone to defend the vessel.

In the following seconds, Butch planned a hurried approach to this incoming threat. He rose in altitude and quickly descended on his foes, taking down two enemy planes during this maneuver. Ascending back into combat, further skill was needed as Butch had to evade the falling meteors that once were Japanese bombers. Once he brought his fighter back to position, Butch was still outnumbered. Seven fighters remained. He danced flawlessly through them, being fatally accurate and economical with his remaining rounds. Witnesses to the epic dogfight sighted three bombers in flames at once. His sixth prey was smoking when Butch’s ammunition ran out. By then, other American fighters had entered the fight.

By the time he landed, Butch was the #1 Naval aviator of World War II. His bravery was recognized instantly. He was nicknamed “Ace” and awarded the Congressional Medal of Honor, the nation’s highest decoration for valor.

Then, Tragedy Strikes

On November 26, 1943, Japanese planes were again reported near an American Navy carrier. Lieutenant Commander Butch O’Hare, leading an exercise on night flying, decided to intercept the enemies with his squadron. The events are unclear, but the ensuing night combat led to Butch’s communication being cut off, and he disappeared into the sea.[24]

Butch’s actions, gigantic symbols of heroism and bravery in times of war, needed to be remembered for generations. In June 1949, a Chicago City Council subcommittee voted—unanimously—to rename Douglas Airport to “O’Hare,” in honor of Butch.[25] A handful of articles and profiles filled newspapers and magazines, all meant to familiarize the public with Edward “Butch” O’Hare and his heroism.

Three months later, 200,000 people paid tribute to Butch’s sacrifice and attended the air show that marked the renaming of the airport. Selma O’Hare was a guest of honor at the ceremony. The day included displays of Naval air power, an appearance by the Blue Angels, and the name “O’Hare” masterfully written in the sky.[26]

Time changes perspectives and legacies. During Eddie’s lifetime, “O’Hare” was connected to the mob and illicit gambling. But Butch’s actions almost erased the association of the “O’Hare” name with Capone, greed, or crime and brought it closer to heroism, sacrifice, and legacy.

Two Grumman F4F-3 Wildcats of VF-3, assigned to USS Lexington (CV-2), 1942. Lieutenant Commander John Smith Thach, U.S.N., VF-3 squadron commander, is flying the Wildcat marked F-1. The second F4F, marked F-13, is flown by Lieutenant (j.g.) Edward Henry O’Hare, U.S.N. (United States Navy)

Sources

[1]O’Hare History,” Chicago Department of Aviation.

[2] “O’Hare Warned of Capone Rage in Prison Cell,” Chicago Tribune, November 13, 1939, p. 8.

[3] “O’Hare Warned of Capone’s Rage,” Chicago Tribune, November 13, 1939, p. 1.

[4]Al Capone,fbi.gov/history.

[5]Racketeering,” Legal Information Institute, Cornell Law School.

[6]Prohibition and the Rise of the American Gangster,” U.S. National Archives, January 17, 2012.

[7]As dice start to roll legally in Chicago, a look back at the city’s underworld gambling history,” by Ron Grossman, Chicago Tribune, March 12, 2024.

[8] “O’Hare Warned of Capone’s Rage in Prison Cell,” Chicago Tribune, previously cited.

[9] “Judge Holland Tells of His Real Estate Deal with O’Hare,” Chicago Tribune, Nov. 13, 1939, p. 8.

[10]  “New Legal hazard for Dogs,” Collyer’s Eye (Chicago, Illinois), September 17, 1927, p. 3.

[11] “Identify Eddie O’Hare as Dog Track ‘Angel’,” Collyer’s Eye and The Baseball World (Chicago, Illinois), August 11, 1934, p. 1.

[12] “Dog Racetracks Face Legal Ban in Chicago,” Collyer’s Eye (Chicago, Illinois), September 17, 1927, p. 1.

[13]So long, Sportsman’s—good riddance,” by Kate Schmidt, Chicago Reader, January 8, 2009.

[14]Al Capone,fbi.gov/history, previously cited.

[15] “Track Setup Described: Patton Explains the Division of Sportsman’s Park Stock,” Chicago Tribune, Nov. 15, 1939, p. 2.

[16]Cost of Living Calculator: What is Your Dollar Worth Today?” American Institute for Economic Research.

[17] “O’Hare Warned of Capone’s Rage,” Chicago Tribune, previously cited.

[18]  “O’Hare’s Fears Told,” Chicago Tribune, November 15. 1939, p. 2.

[19] “O’Hare Warned of Capone Rage in Prison Cell,” Chicago Tribune, previously cited.

[20] “O’Hare Warned of Capone Rage in Prison Cell,” Chicago Tribune, previously cited.

[21] “Sleuth’s Story Confirms Scoop on O’Hare Death,” Chicago Tribune, April 21, 1947, p. 5.

[22]America’s First High-Profile Forensic Accountant,” By D. Larry Crumbley, American Board of Forensic Accounting.

[23] “Sleuth’s Story Confirms Scoop on O’Hare Death,” Chicago Tribune, previously cited.

[24] “Gratitude of the Republic,” Chicago Tribune, April 20, 1947, p. 22.

[25] “Vote O’Hare and Meigs as Airport Titles,” Chicago Tribune, June 8, 1949, p. 1.

[26] “200,000 Join In Dedication O’Hare Field,” Chicago Tribune, September 19, 1949, p. 1.

About the author: Gustavo Azevedo

Gustavo Azevedo, a student intern with RPWHS, loves telling stories, and during his internship, he is eager to spotlight some of the more noted residents of Rogers Park. He moved to the United States from Brazil in 2013 and to Rogers Park in 2022 after a year abroad. Gustavo is a Multimedia Journalism major at Loyola University Chicago. He loves films, games, and photography, After graduation in December 2024, he hopes to work in video production.

About the author: Homer Johnson

Homer Johnson first arrived in Rogers Park in 1964 after taking a job as a Psychology professor at Loyola University. he took an active role in the neighborhood, including the campaign to pass the Lakefront Protection Ordinance in 1973 and the fight to save Warren Park, two major movements in local activism in the 1970s.He became the chair of Loyola’s psychology department in 1973 and taught at the university until his retirement. Homer first joined RPWRHS soon after it was founded, was President of the Rogers Park Community Council and led the school councils at both Kilmer Elementary and Sullivan High School when his children were attending. Since retiring Johnson has moved into the Admiral Retirement Center in Edgewater, but remains active in Rogers Park community causes, including the RPWHS Task Force behind the Campaign for Pollard Park.