What distinguishes newspapers is how they cover crime. For the Chicago Sun-Times, crime was the staple it could not get enough of. When I got there in 1966, the paper had three star reporters whose bread and butter was writing about high-profile crimes. To talk to them casually, however, you’d never know what they did for a living.
My fellow reporter during the late 1960s, John Adam Moreau, said flatly the other day that everyone he knew at the newspaper then who was over age 50 had a drinking problem. That would certainly apply to Ray Brennan (pictured exhaling tobacco smoke at left). Legend has it Ray once disappeared from the city room for more than a year. Then one day he reappeared, sat down at his desk and began making phone calls. “Where you been, Ray?” someone asked. All Brennan said was, “The bridge was up.” John Adam once asked Ray if this story were true. “I won’t deny it,” Ray responded.
There are lots of Ray Brennan stories. A 1952 Time magazine piece about Ray began thusly: “The Chicago Sun-Times’s Ray Brennan, 44, is a fast-thinking, fast-moving reporter who modestly puts down his long list of beats to ‘good luck.’ Once, while working in Chicago for the Associated Press, he made a routine long-distance checking call to Crown Point, Ind., and got the county prosecutor on the wire just in time to get a big exclusive: Gangster John Dillinger had crashed out of the Crown Point jail. Last week another and bigger beat landed Reporter Brennan in trouble. In Washington, a grand jury indicted him for impersonating a government employee. (Maximum penalty: three years in prison and a $1,000 fine.)”
In 1950, a U.S. Senate committee led by Senator Estes Kefauver of Tennessee had asked a Chicago police captain named Daniel (Tubbo) Gilbert to testify. Gilbert spent lavishly, and in fact was tagged “the world’s richest cop.” He was also running then for sheriff of Cook County. However, Kefauver would not release Gilbert’s secret testimony, perhaps because Gilbert was a fellow Democrat.
So Brennan went to Washington, appeared at the office of the stenographic service that recorded the testimony and, saying he was office manager of the Kefauver committee, asked for a transcript of Gilbert’s appearance. He got it. Back Ray went to Chicago, where the next day’s Sun-Times splashed Gilbert’s incriminating testimony all over the front page. Tubbo lost the election and as Time reported, Brennan was indicted. In time the charges were dropped.
One day between deadlines Ray and I got to talking. In the early 1950s, he said, the Sun-Times was your typical big-city tabloid of the sort that mothers of young children didn’t want seen around the house. The paper’s editor then, Milburn P. Akers, was determined to elevate the image of the Sun-Times. As Ray told the story, Akers began weening the paper from its daily diet of blood-and-gore stories by tackling more serious subjects. But he wanted to keep the newspaper’s fingers in the crime bowl. To do so, Akers assigned Brennan to cover high-profile criminal trials all over the U.S. This Ray was happy to do. He wrote well, ate well, drank well on the paper’s expense account for several years, following explosive trials from city to city. Maybe that’s where he was those 53 weeks.
Ray wasn’t afraid to get to know gangsters. His most notorious association was with Roger Touhy, who made a fortune as a Chicago bootlegger during Prohibition, in the process becoming a rival of Al Capone. Touhy was convicted in 1934 of the kidnapping of John (Jake the Barber) Factor, brother of cosmetics kingpin Max Factor, Sr. However, there was also evidence that Capone had done the kidnapping as a way to implicate Touhy and get him out of the picture.
Decades later, in 1959, Brennan became the ghost writer of Touhy’s autobiography, The Stolen Years, which was instrumental in getting Touhy paroled from prison in Stateville, near Joliet. (That’s the two of them in Touhy’s prison cell.)
Three weeks later, Brennan and Touhy met for dinner at the Chicago Press Club. They discussed a lawsuit filed against Touhy by Max Factor. Then the men parted and Touhy returned home. On his front steps, he was gunned down and died soon thereafter.
I will say this: For a man who had lived the life he did, Ray Brennan was about the nicest and most likable man I’ve ever met. He died in 1972 of cancer, probably because like so many others of us, he was never without a cigarette in his hand.
Sandy Smith was another of the Sun-Times crimestopper team. Sandy worked at the Chicago Tribune for 20 years before crossing Michigan Avenue to join the Sun-Times in 1963. His specialty was writing about the Chicago crime syndicate. Nobody in Chicago journalism—not even Art Petacque at the Sun-Times or George Bliss at the Tribune—had better sources within the FBI than Sandy Smith. Sandy was brash, too. He’d show up uninvited at the parties of Chicago mobsters, the weddings of their children, and also their funerals (the mob had a habit of killing its own).
Around the city room, however, he was an unassuming guy. His passion was fly fishing. Sandy left the newspaper in 1967 to work for Time and eventually moved to Montana, I suppose to be closer to the fish. He died in 2005.
The third of this trio was the great Art Petacque. Art was bigger than life and deserves a book of his own. I can’t do that, but I’ll tell you his story another day.