A Prohibition Shootout on the Streets of Bay Ridge

Owl's Head Tavern
The Owl’s Head Tavern, ca. 1939. NE corner of Bay Ridge and Third avenues. Via department of records

Part of an ongoing, irregular series of historical articles called True Crime: Bay Ridge.

Sgt. Johnny McGarty worked at a police station on Hamilton Avenue, at Rapelye Street, since torn down for the BQE. But he lived in Bay Ridge, and he had just gotten off the subway at the Bay Ridge Avenue stop, dressed in plainclothes, on Tuesday, March 19, 1929, at approximately 1am, when he heard the gunshots, first two, then six more—as he’d later describe them, “a regular volley.” As he told it:

I ran down the street [69th Street, toward Third Avenue] and I saw a man chasing another man and firing at him. There were others dodging here and there, and there was lots of shooting.

I shouted that I was a policeman, but maybe they didn’t hear me. Anyway, the two men dodged into a storm door and I went in after them. [McGarty saw the man with the pistol bending over the other man, who had been wounded in the leg…McGarty ordered the man with the pistol to throw up his hands. “Instead…he swung around and fired point blank at me. He missed and I emptied my pistol into his body.”] I fired four times and he toppled over. The other man jumped by me, and he fell just outside the door.

I had to rap the revolver out of the hands of the man who had fallen. He looked up at me and mumbled, “I’m a cop.” Naturally I bent down over him, and he said, “I know you, you’re a sergeant in the 39th.” Then I asked him to tell me what had happened, and he asked me to get him a priest. He wouldn’t tell me a thing. He stuck out his hand, though, and I shook it.

Patrolman Maloney
Patrolman Maloney

The dead cop was Patrolman Daniel Maloney, of 576 77th Street, and he “was certainly not doing police duty,” the police commissioner said the next day. Maloney had been at a meeting of supposedly rival bootleggers at the Owl’s Head Tavern, a cafe and speakeasy on the northeast corner of 69th and Third, now a 99 Cents Store. (In March 1929, prohibition had been law for nine years, its repeal was still four years away, and the stockmarket wouldn’t crash for seven more months.)

Charles “Vannie” Higgins had had his trouble with Tommy Connell, is what the papers said. Higgins was an above-average gangster, a Bay Ridge native known as the “czar of Brooklyn liquor interests,” though he strongly denied it. Maybe he wasn’t, but “the fact of the matter is, however,” the Brooklyn Eagle later reported, “that Higgins rose from the status of a mere taxi operator, that he now owns a fleet of cabs, that he has a great interest in aviation, and that he operates two seaplanes, both of which seem able to fly only at night.” (Higgins lived in an apartment at 7420 Ridge Boulevard, to the frequent consternation of his neighbors.)

Charles Vannie Higgins
Charles “Vannie” Higgins

Connell, Higgins’s supposed rival, was a “quiet, sedate young man [with] an interest in bootleg liquor in the same section.” Higgins and Connell had met, investigators believed—at least at first—to hash out their disagreements. Higgins brought a few friends—one of whom was an ex-cop, who’d resigned, he’d said, over police harassment of his friend Vannie, and ever since had been at his friend Vannie’s side day and night—and they all brought their wives, the Eagle reported, “to make Connell certain that everything was all right.”

But it wasn’t. The bartender at the Owl’s Head said the late Patrolman Maloney had showed up and demanded to speak to Connell; a shot was fired indoors, and then Maloney pulled Connell out into the street. “After that on the street the shooting became general.” More than 60 shots were fired by the time the gunfight was over. Everyone ran. Connell “couldn’t have escaped,” the Eagle reported—he had been shot in the right leg, probably by Maloney. “He tried to crash out of a storm door which hides the side entrance to the Tavern, and crumpled up at McGarty’s feet,” the Eagle reported.

“Paul Eckert, who is a vague sort of person, who looks very amiable in his stout, innocent blond way, stuck near Connell. He did try to run, but Eckert isn’t built for running, and McGarty caught him.”

Higgins was captured on 69th Street. He’d been hiding behind a parked taxi, which almost ran him over when it pulled out with “a highly excited policeman who wanted to make sure he caught somebody in all that fracas” in the backseat. (This incident was later used in a letter-to-the-editor as a reason not to legalize street parking—it offers a hiding place to gangsters!) “Higgins insisted he was running away for protection. Patrolman Reed pointed out that if he was afraid of the shots he’d have ducked for a doorway. So they took him to the Fort Hamilton station.” Higgins’s associates, the Bills Benson and Bailey, escaped.

Another man, Harold Richardson, of 8678 Bay Parkway, was also shot; he “felt the sting of a bullet in his left leg as he was walking to a rear room of the tavern from the bar,” he later testified. But police believed he was an innocent bystander. “The shot, [Richardson] said, was fired from outside.”

Owl's Head shootout gang
The gang at court. The caption is wrong: Higgins is on the right. Of the rest, not sure who’s who. Via Brooklyn Eagle

This short-lived blaze of barking bullets became known (briefly) as the Battle of Bay Ridge, a bona fide, beer-fueled gang war and tabloid sensation. Higgins, Connell and Eckert were arrested and arraigned in Fifth Avenue Court the next day. “This trio, appearing diffident and looking misjudged…all pleaded not guilty…and all were held without bail,” the Eagle reported. “Then Connell, who had been limping around all day, came near to swooning because of his wounded leg. They sent him to Swedish Hospital.”

Bail was later set at $5,000. Higgins and Eckert posted it, left together in a car, and dropped out of sight.

Maloney, the dead patrolman, seemed to be the key to whatever had happened. He was found with four revolvers—one in his hand, two in his pockets and another in his holster. “He had no right to be where he was shot,” the police commissioner said. “We cannot understand why he had four revolvers on his person…He certainly had no police reason for carrying so many guns.” Another firearm was “as wicked-looking a sawed-off shotgun as one would want to see” with “a heavy curved handle and two short, ugly barrels.” It was found near Connell. “He had no ammunition for it, however,” the Eagle reported. “Maloney did. A box of cartridges for the gun were in his pocket. The gun most certainly had been discharged, too, because when Patrolman Reed picked it up it was still smoking.”

Owl's Head shootout
Via Brooklyn Eagle

One of the pistols was a police service revolver that didn’t belong to Maloney—its serial number was 9969, or maybe 6966, so the men associated with both were brought in for questioning: John Shea, an active patrolman at the station on W. 100th Street in Manhattan; the other, John Brady, dismissed from the force in January 1928. It was finally discovered to belong to Bartley Hannan, who’d resigned three years earlier and convinced investigators that his gun had been stolen two years earlier.

Detectives believed Patrolman Maloney had been with Connell to a different speakeasy, on 69th and Fourth, before the shooting, where they’d been drinking—though friends later said Maloney never touched liquor. Connell left with Higgins’s peace party but without Maloney. “It is certain that Maloney went to the Tavern carrying a young arsenal, but whether he started the shooting or not is something that hasn’t been determined,” the Eagle reported.

However, it is true that in the general firing no one was hurt. It was only when McGarty came that the deadly shooting seems to have begun. Up to that time a great many guns had been fired, but when the police began their roundup the only ones they could find were the revolvers Maloney had…all 38-caliber, and the sawed-off shotgun.

Owl's Head shootout
The police commissioner visits the crime scene

In fact, no one could (or would) say they saw anyone shooting but Maloney. The felonious assault charges against Higgins, Connell and Eckert were discharged after the trial, in April 1929, at which the nine witnesses who testified, including four cops, didn’t say they’d seen anyone else do any shooting. Still, a week and a half later, cops raided the Owl’s Head Tavern and found 10 half-barrels of beer in the cellar; the waiter was arrested, and a co-owner, Fred Brendt, was followed to and arrested at his home, at 628 E. 26th Street, in Midwood, where “a large quantity of assorted liquors” was confiscated. Regardless of all this negative attention, the Owl’s Head Tavern remained open at least into the 1960s.

An odd aside: a few months after the trial, in August 1929, in Long Beach, Long Island, “Edward Thomas” was shot at the Indoor Yacht Club, at Ocean Front Street and Wyoming Avenue. Police afterward were looking for “Handsome” Thomas J. Slattery, also known as “Big Tom,” “well-known and feared some years ago along the Brooklyn waterfront,” the Eagle reported, as a honcho in the Ironworkers Union. He was also once a co-owner of the Owl’s Head Tavern, and the rumor was that Thomas was a stool pigeon for Prohibition Agents, though authorities denied it.

Edward Thomas, whose real name turned out to be Thomas E. Russell, staggered into the local station house after midnight and requested medical attention. The bullet had entered his body above the heart and “glanced off the spine.” Russell told the cops that Slattery had shot him, and that several other men had been at the club when he was shot; police blew a siren blast, a signal to raise Long Beach’s drawbridges, its main traffic exits, and they remained up until guards could be posted.

Slattery’s car was in front of the club, but he wasn’t there; no one was. Slattery also wasn’t home—nearby, on Vermont Street—either. He was picked up the next day, but Russell dropped the charges a week later from Long Beach Hospital, when it became clear that he’d live. (He was subsequently charged with perjury.) Slattery was immediately rearrested for running a speakeasy, and he died two months later, in October, of hemorrhages, apparently in connection with an operation a year earlier to remove a rib.

In the 1940s, the Vannie Higgins story was featured in the first issue of Crime and Punishment, a true-crime comic book dedicated to the “eradication of crime.” It even featured scenes from the Owl’s Head shootout, hilariously rewritten so that Maloney is an honest cop who just happens to be on the scene; McGarty accidentally shoots him when a bullet meant to scare Higgins ricochets off a plate. “Poor Maloney,” the ghost of a different cop, who’s trailing Higgins, says over the patrolman’s dead body. “He’s got a couple of kids, too!”

Owl's Head shootout
Via Comic Book Plus

No one really believed that’s what happened, although the case remained foggy. The dominant theory about the shooting was that there had been “a break in friendship” between Maloney and Connell. “It may be…that Maloney was afraid of what might happen if Connell patched up his troubles with Higgins.” Then again, “There are men about town who say that Tommy Connell and Vannie Higgins…never would have held a peace conference such as seemed to be going on when the guns began to bark,” the Eagle reported.

What perhaps came to puzzle detectives most was the role of Bill Benson, once one of Higgins’s “ablest lieutenants”; investigators came to believe the two had started fighting shortly before the shootout. Benson had been present at the Owl’s Head, but cops couldn’t find him afterward. He disappeared. He didn’t come forward to help his boss. He stayed undercover, though he eventually resurfaced, after he was no longer wanted in connection with the shootout.

Higgins didn’t. Higgins had been known to the police before the shootout, having been arrested eight times. He was convicted twice, of assault, in 1915 and 1916, both times placed on probation. Otherwise, his cases were discharged: in 1926, for assault, then for robbery; in 1928, for possessing a revolver, for homicide, for grand larceny, for felonious assault, and again for homicide.

Higgins died three years later, shot by Murder, Inc., agents on Union Street, just west of Prospect Park, as he was walking with his family, including his 7-year-old daughter, after her tap-dance recital, around 1:30 a.m. It made the front page of the Times, which called him a “rum runner, night-club owner and most powerful underworld leader in Brooklyn since the death of Frankie Uale.” He’s buried in Middle Village, Queens, in the same cemetery Shore Road spinster and gory-murder victim Victoria Muspratt would be buried in two years later.

Vannie Higgins death in New York Times
Via eBay

As soon as he was left off for the Maloney incident, “he went to Baltimore,” the Eagle reported, the home-city of that other man, Eckert, who had been arrested. Higgins “has been making that city his headquarters ever since. He has returned to Brooklyn every now and then, but for some reason, perhaps known only to Benson and to Higgins, he comes in very infrequently, and when he does arrive it is without a brass band or advance notices.”

It has never been fully explained why Tommy Connell…who was not friendly with Higgins, should have been in Owl’s Head Tavern with the latter that night. Connell was doing pretty well in a business way, and was cutting in a little on the business of Higgins. Why a peace conference should have been arranged, if it was arranged, under the circumstances, is a mystery that has baffled the detectives. They are also wondering why every one went to the peace conference carrying a gun.

“Police are investigating…but they are getting no help from those who know what it was about….Since none of [those arrested] will talk, and since their wives profess to know nothing, and since two other men who were in the party couldn’t or wouldn’t tell much, the rest is entirely supposition…”

“There are lots of things they don’t know, and lots of things they probably will never find out.”

One of the few things we do know is that Higgins, that Brooklyn prince of bootleggers, gave his address to police as the Hotel Stafford, which the Eagle reported was in Manhattan, on 93rd and Third. The paper was almost certainly mistaken: surely it meant the Hotel Spafford, actually at that corner in Brooklyn—the old name for the Prince Hotel.

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