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Valentines

November 2023
4min read

Back when the Franks and the Goths were trying to muscle in on the Roman Empire, a pagan priest named Valentine offered succor to persecuted Christians. Eventually he converted to the new religion and was clubbed to death for his trouble. St. Valentine’s feast day absorbed the trappings of a Roman fertility cult. It’s been linked to hearts and flowers ever since, but in Chicago it brings other associations to mind.

After the death of Hymie Weiss, the North Side mantle fell to George Moran, a thug of Polish extraction. His temper tantrums earned him the nickname Bugs.

Moran, whose qualities of leadership were minimal, continued to cause trouble for the Capone outfit during the years of relative peace. He lent at least tacit support to another North Sider with ambition named Joe Aiello. Aiello mounted a number of attempts to assassinate Capone. He offered a fifty-thousand-dollar open bounty on Al’s life. (Aiello’s elegant home stands a few blocks from the site of the Tim Murphy shooting, at 2553 West Lunt Street.) Two of Moran’s men, Pete and Frank Gusenberg, wounded Capone’s bodyguard Jack McGurn in a phone booth.

Early in 1929 Moran purchased a shipment of Canadian Old Log Cabin whiskey that had allegedly been hijacked from Capone. The hijackers soon offered another shipment for an attractive price. Moran was to oversee delivery personally—on St. Valentine’s Day.

February 14 dawned cold and dismal. By ten in the morning seven men were waiting at a garage at 2122 North Clark Street. The sign outside read S.M.C. CARTAGE co. The place was a depot for Moran’s bootleg operation. The occupants included four Moran associates and the two Gusenberg brothers. The seventh man, twentynine-year-old Reinhart Schwimmer, was a sometime oculist who thought it glamorous to hang out with hoodlums.

Before Moran arrived, perhaps as he approached the building, a police car pulled up in front. Two men in uniform and two in plain clothes entered the building.

Schwimmer must have been scared. The others had endured the nuisance of police raids before. They had little to worry about—this was Chicago—but Reinhart had no record. His mother was still supporting him.

In any case, no one was given an opportunity to explain. The men were ordered to line up along the wall, their hands in the air. The “police” then opened fire, shredding the victims with seventy shots from two machine guns and two shotgun blasts.

Eight minutes after entering, the men in uniform marched their two companions back to the car as if arresting them. They disappeared.

The men in the garage, save one, were dead. Frank Gusenberg survived to be taken to Alexian Brothers Hospital. Loyal to the underworld code of silence, Frank insisted, in spite of his perforated torso, that “nobody shot me.” He died within hours.

S.M.C. Cartage remains the bestknown crime site in Chicago. A Mr. and Mrs. Werner operated an antiques store there in the 1940s. At first they knew nothing of its history and were mystified by the steady stream of crime buffs eager to gaze at the building’s back wall. “They came from all over the world,” Mrs. Werner said, “even New Zealand.”

The building was demolished in 1967. The site is now the grassy lawn and parking lot of a nursing home. But the rest of the mixed residential block is intact, including the houses across the street, at 2135 and 2119 North Clark, where for days lookouts tracked Moran’s movements.

Not too far away, at 2221 North Lincoln Avenue, is the building that was the Drake-Braithwaite Funeral Home, from which the victims of the St. Valentine’s Day carnage were buried. The two widows of the bigamist Frank Gusenberg appeared at the wake and provided a bit of comic relief. The Tribune reported that they vied with each other in singing Frank’s praises.

Gangland slaughter was nothing new, but on St. Valentine’s Day the number of victims reached a critical mass. The affair instantly became a massacre. Suddenly the criminal infestation of the city seemed out of control. Citizens suggested that the U.S. Marines, who’d been occupying Nicaragua for three years, would be better employed patrolling Cook County. The who and why of the operation continues to inspire debate among crime buffs. Did Capone, who was soaking up the sun at his Miami estate that February, order it? Was it rogue police officers with a grudge against Moran? A Frederick R. Burke from St. Louis was later caught with the machine guns used in the massacre, but even his participation in the killing is uncertain.

The consensus is that “Machine Gun” Jack McGurn organized the killings for Capone. LeVell even suspects McGurn to have been one of the shooters. He points out that McGurn had been spotted in nearby Lincoln Park and that at least one witness claimed to have seen him outside S.M.C. Cartage that morning.

“McGurn was the epitome of the gangster,” he says. “He drove a roadster, he was a playboy, and he was probably the most dangerous gunman who ever walked the streets of Chicago.”

For years McGurn played Lancelot to Capone’s King Arthur. A true “Jazz Age sheik,” he dressed to the nines, could tear up a dance floor, and played a skillful game of golf. His companion was a striking blonde named Louise Rolfe, herself a tournament-level golfer. If McGurn’s good looks were more Latin than Celtic, it was because he was in fact Sicilian, born Vincenzo Gibaldi. He acquired the Irish moniker during a brief boxing career. In 1929 he was still only twenty-six.

“He was a hit man who hit hit men,” LeVell explains. “He took care of guys who were gunning for Capone, guys who were armed and on their guard.” McGurn may have killed twenty-two men, as the police stated, or he may have killed twice that many. Once pulled in for questioning about a mob rubout, he was asked if he knew the victim was dead. “Dead?” he replied. “I didn’t even know he was sick.”

The prohibition agents who marched out to enforce a deeply unpopular law earned a top salary that was less than a garbage collector’s.

McGurn claimed he’d spent St. Valentine’s Day in an appropriate manner: in bed with Louise at the Stevens Hotel on South Michigan—one of the swankiest addresses in the city, now the Chicago Hilton. The papers christened Louise “The Blonde Alibi” and quoted her as saying, “When you’re with Tack, you’re never bored.”

Seven years later, his glory days over, McGurn went bowling at 805 North Milwaukee Avenue. It was St. Valentine’s Day. Shortly after midnight unknown gunmen surrounded him and shot him dead. They left a comic Valentine with the body. The bowling alley is now an office-furniture store.

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