Now Playing

Chicago newspapers bannered the 1929 Massacre on North Clark Street, in which seven men w

Infamy and Fortune

by William J. Helmer | Men's Book Chicago magazine | March 15, 2012

It’s like the story of the St. Valentine’s Day Massacre has been carved in stone.

Every book, countless newspaper and magazine articles, even the 1967 Jason Robards movie, all describe how Al Capone suckered Bugs Moran into buying a truckload of whiskey at his North Clark Street garage on Feb. 14, 1929. Then two gangsters dressed as cops disarmed the seven occupants, who were mowed down by men with submachine guns. After the shooting, our cops marched our gunmen, hands raised as though under arrest, out to a Cadillac that looked like a detective car and escaped.

Over the years this mass murder has been described as a “Valentine From Al Capone,” “Al Capone’s Valentine,” or variations.

In the course of writing about the exploits of Chicago gangsters I began discovering new accounts of these killings, mostly by retired detectives and journalists who had stayed on the case, sometimes for years. Then I learned that a similar scenario had been published in a crime magazine by Arthur Bilek, a one-time Chicago cop who became chief of the Cook County Police, then a college professor, and since then a director of the Chicago Crime Commission. I contacted him when he was a professor, and we collaborated on a book titled The St. Valentine’s Day Massacre.

It seems that virtually all the “Massacre” accounts since then derive from newspaper reports of the day. And except for the date of the killings, the victims and the Cadillac, all have been off the mark. Very far off.

Though space limits us from going into all of the details, the killers actually came from the battlegrounds of St. Louis when that city’s gangs fell apart, and at least four were hired by Capone as a special-assignment crew because they were unknown to both the police and Moran. They included Fred Burke (in whose house the submachine guns were later found), Gus Winkeler (spelled “Winkler” when he was later taking over much of Moran’s North Side), Ray Nugent (called “Gander” or “Crane-neck”), Bob Carey (called “Gimpy”) and Fred Goetz (aka George Zeigler, usually misspelled “Ziegler”), the last being a Chicagoan with St. Louis connections. Goetz’s young friend, Byron Bolton, was mainly a gofer, but he supposedly knew Moran by sight and became one of the Clark Street lookouts. Five years later, after Bolton’s arrest in a federal kidnapping case, the Chicago American devoted much of its front page to proclaiming the Massacre “solved.”

The paper refused to reveal the article’s source, and Bolton, who was already in federal custody in St. Paul, denied having any part in releasing it. J. Edgar Hoover immediately declared every word of it false—but he was greatly annoyed that his St. Paul men had focused all of their attention on a kidnapping case that was eclipsed by the “Massacre-solved” newspaper story. So the G-men quickly squeezed Bolton for a much more detailed account, which contradicted much of the story printed in the Chicago American.

Hoover was later compelled to send this in a confidential memo to a Justice Department superior, naming the actual shooters. And his account was independently confirmed in the unpublished memoirs written in 1934 by the widow of Gus Winkeler after he was killed. Those papers have now become the basis for a book recently published by Indiana University Press, Al Capone and His American Boys—“American boys” being the expression used by Georgette Winkeler.

It seems that in the fall of 1928 Capone, with Gus Winkeler, Fred Burke, Fred Goetz and others, including two politicians, met at a Wisconsin estate owned by Capone but managed by Goetz, with Bolton catering the meals. There he targeted Bugs Moran in particular and left for Florida, turning the job over to Frank Nitti, who passed it on down the line. The logistics were left to Claude Maddox (aka John Moore, or “Screwy”), a hoodlum originally from St. Louis who by then was running a small affiliated gang out of a café on the edge of Moran’s North Side territory.

The Capone mob believed that Moran would be assembling his men to retaliate after an attempt to kill him outside a nightclub the previous month, and that he probably wasn’t keen on having a bunch of known gangsters coming to his residence at the Parkway Apartment Hotel. They were correct: Moran himself told his gang to meet him around the corner, in his “S-M-C Cartage Company” garage at 2122 N. Clark St., on a Thursday, which just happened to be St. Valentine’s Day.

By two strokes of odd luck, Maddox had to be in court that day; and Moran “missed a bullet” by arriving late: Seeing what looked like a detective car in front of the garage, he decided he didn’t need the grief of an arrest or a shakedown, a common practice of Chicago police at the time. For his part, Bolton made the mistake of confusing another gangster with Moran and called in the shooters. He also, stupidly enough, left behind some conspicuous clues—either a prescription medicine bottle with his name on it or a letter from his family in downstate Illinois, or both.

The killers, in fact, used two cars—the Cadillac that everyone saw leaving the scene, and a Peerless behind the garage. The two phony cops came out of the Peerless, according to a youngster and his friend who were walking down the alley. The supposed cops slipped in the alley door and disarmed Moran’s men, who were huddled around a coffee pot in the back. Then one of them opened the front door for the men with submachine guns, who otherwise would have had to make their way past several trucks and cars to reach their victims, seven of them now lined up against a wall. And because the shooters did not know who was who and wanted to take no chances, they killed them all. Hence the “Massacre,” as every newspaper in the country called it.

A few days later, when the Cadillac was being dismantled in a private garage near Maddox’s café, a gasoline explosion set fire to the place; and a few days after that another phony detective car—the Peerless, in which cops found the address book of Massacre victim Albert Weinshank—was partly blown up in a vacant lot in Maddox’s Maywood neighborhood. (This had been reported by a youngster walking in the alley behind the Clark Street garage, but he and the Peerless car only made news for a day or two.)


• The Massacre was not a deliberately ironic “Valentine” from Al Capone; the meeting had been called by Moran himself, probably because of an attempt on his life outside the Chez Pierre nightclub on Chicago’s North Side in mid-January. (Why else have lookouts watching the S-M-C Cartage Company garage for nearly a month?)

• The hijacked whiskey story was based entirely on a wild guess by a federal Prohibition official, later fired, who insinuated himself into headlines that same day by blaming the killings on rogue cops (before he died, Frank Gusenberg said, “The cops did it”). Our Fed also had heard of a recent hijacking but wasn’t aware that Moran’s meeting included his top lieutenants in their spiffy outfits rather than his regular workmen.

• Jack McGurn (who acquired his nickname “Machine Gun” only after he became a Massacre suspect) certainly must have known of Capone’s intentions to waste Bugs Moran, but by 1928 McGurn already was notorious as a ranking mob killer; and when surveillance of Moran’s S-M-C Cartage Co. garage began he holed up in Michigan Avenue’s elegant Stevens Hotel with his girlfriend, Louise Rolfe (the “Blond Alibi”). For the next 60-some years she insisted that Jack had been in the sack with her that morning. (Ironically, the Massacre’s quickly assembled task force held its meetings one floor above.)

• The lookouts were not Detroit’s Keywell Brothers, as initially reported because a woman witness had “partially identified” one of them. When she later decided she was mistaken this earned her only a one-sentence mention in some of the local papers.

• The police failed to follow up on a dozen leads indicating that the shooters were a crew originally from St. Louis, but these findings of the then-independent detective bureau were ignored. (When each of these gunmen later were killed or died, each was named in newspapers as a “suspect” in the Massacre; and after his 1935 arrest by federal agents Bolton had claimed that Chicago’s chief of detectives was on Capone’s payroll.)

• After Fred Burke killed a traffic cop in St. Joseph, Mich., the following December, a police raid on the house of a “Frederick Dane” (soon identified as Burke) turned up a small arsenal that included the two submachine guns used in the Massacre. Burke escaped arrest at the time but would spend the rest of his life in Michigan’s state prison, raising birds.

With Capone and Burke both sentenced or in prison by late 1931, the “American boys” went their separate ways. “Gimpy” Carey and a girlfriend headed for Washington, D.C., and then to New York City, where both were found dead (their killings went down as a murder and a suicide, but this has been doubted).
Nugent moved to Miami, opened a tavern, bought the wrong brand of beer, and his body was never found, possibly thanks to alligators.
Gus Winkler returned to Chicago in the early ’30s, and using the name “Michael Rand” began acquiring “respectability” by opening fashionable nightclubs on the North Side. He was shot to death (probably on orders of Capone’s successor, Frank Nitti) in 1933 at the front door of a beer-distributing business that he secretly owned.
Fred Goetz (aka “Shotgun George” Zeigler) was himself shotgunned on a downtown street in Cicero in 1934.
As for Bugs Moran, he later ventured back to the Chicago area, tried to get slot machines into taverns north of the city, and after that his crime career spiraled downward into bank robbery. He died in prison in 1957.
Chicago police seemed to make a point of never pursuing the matter. All of the original “suspects” had to be released, and the case went cold, except for the life it still lives as the “gangland crime of century.”