Gangsters of New Haven: The Italian Whitey

The following is the first in a series about the mob in New Haven, Connecticut… It started off originally as a story about William Grasso — but while researching him, we found ourselves spending more time on Grasso's mentor, and decided an even more worthwhile series would detail his exploits first...

Ralph “Whitey” Tropiano.
Ralph “Whitey” Tropiano.

Connecticut had a peculiar relationship with organized crime. Located at about the midpoint between New York and Boston, it never had its own formally designated crime family. However, due to its proximity to New York and Boston, it always attracted attention and several crime families had interests in the state over the decades.

The notoriously bad-tempered, yet supremely disciplined  William (The Wild Man) Grasso, who rose to become underboss of the Patriarca crime family under Raymond Junior, once reminisced with an associate about old times and noted how he’d gotten his big break. It arrived in the form of a 10-year prison sentence.

“Best thing that ever happened to me was when they sent me to Atlanta,” he’d said.

He came up under a notoriously violent member of the Colombo crime family (when it was still the Profaci crime family) who in the 1930s allegedly had been a member of that elite crew of killers known as Murder Incorporated.

New York police were well acquainted with Ralph “Whitey” Tropiano. Aside from reports of him being a triggerman for Murder, Inc., he was suspected of involvement in multiple unsolved murders stretching over years in Brooklyn. He’d actually been arrested for two of those homicides, but was released when witnesses  either refused to testify or vanished off the face of the earth before they could.

Whitey was born in August 1912 in New Haven, the second of five children, to immigrants from Naples. Whitey’s father, Biagio, a barber by trade, also worked as a bartender at Sabatini’s Cafe in downtown New Haven. Because of a need to conserve grain for World War I, a pre-Prohibition ban on hard liquor was implemented in December 1919; Prohibition didn't officially start until later in January 1920. The 1919 ban proved fateful. Shortly after Christmas that year, more than 70 people in Connecticut and western Massachusetts died from alcohol poisoning after consuming wood alcohol that had been allegedly served by Biagio at Sabatini’s. (The  newspapers dubbed the stuff "murder” or “poison” whiskey.) Biagio was among those arrested for alleged involvement. Biagio was released, however, when someone firebombed the café, thereby destroying all of the state’s evidence.

Some have called the episode a foretaste of the pending lawlessness and corruption associated with New Haven and most of Connecticut during the Prohibition years. The state’s population consisted largely of immigrants from southern Europe, including Italy, as well as Ireland, Germany, and Poland, all places where drink -- whether beer, wine, or the harder stuff -- was beloved and considered life's necessary lubricant.

Interestingly, Connecticut and Rhode Island both refused to ratify the 18th Amendment, the law that banned the manufacture, sale, and transportation (but not the consumption) of alcohol. The Connecticut state senate defeated ratification by 20-14. Local newspapers and citizens of Connecticut enthusiastically applauded this defiance, with the Hartford Courant calling Prohibition "a highly dangerous invasion of the rights of individual states." The New Haven Journal Courier proudly proclaimed: "Connecticut is alone entitled to raise the flag of freedom in her hands and wave it aloft." Connecticut, however, did eventually ratify it, on May 6, 1919, after it was added to the Constitution.

Still, both Connecticut and Rhode Island were downright hostile to the very idea of Prohibition. As of 1921, some 1,500 saloons were open for business in Connecticut, and no less than 400 were located in New Haven alone. As for Rhode Island, its southern border touched the Atlantic ocean, and that hunk of coastline served as a major artery from which illegal booze flowed inward from Canada, the Bahamas, and other places.

Such was the backdrop against which the Mafia established itself in New Haven, it's roots running so deep, it's alleged that they endure to this day.

Whitey wasn't there to benefit from that however. His father, Biagio, was arrested again in 1921, that time on a drug charge and to avoid a descent into abject poverty -- Whitey’s mother had never learned to speak English well so seeking help from New Haven’s welfare department was especially challenging for her -- sometime in 1922, the family moved to Bath Beach, Brooklyn, where they had relatives. Whitey took after his dad, though, and already had a record, having been arrested at age 9 for stealing a bike.

In the summer of 1952, New York City detectives went to Point Beach, Milford on a mission to find the man who murdered Arnold Schuster earlier that year. The 24-year-old clothing store salesman had been riding on the subway in downtown Brooklyn on February 18 when another passenger caught his eye. Schuster followed this man after he left the train at Pacific Street. Certain he was trailing infamous bank robber Willie Sutton, Schuster tipped off police, who arrested Sutton.

Schuster would be applauded for his "heroism" -- and did a circuit on television news segments discussing his encounter with the wanted bank robber. Then he was gunned down in Brooklyn right outside his home on March 8, 1952, less than one month after the serendipitous subway sighting. The night of the execution — Schuster had been shot four times, once in each eye and twice in the groin —saw the crime scene flooded with the police chief, several high-ranking officers, and 75 detectives.

A decade after the murder of Schuster, the New York World-Telegram & Sun reported key data: there had been 1,688 investigations involving 412 law enforcement agencies who questioned 363 known criminals.

Albert Anastasia, the feared mob boss, supposedly grew incensed watching Schuster on one of his TV interviews and barked the order: "kill 'im!"

Albert Anastasia

The killing shocked the city and sparked a massive manhunt that brought those New York City detectives to Milford. They had information that the 39-year-old Brooklyn hoodlum named Ralph “Whitey” Tropiano, who recently moved to Connecticut, was pals with the prime suspect. Said suspect had been spotted visiting Whitey at his Milford home.

A handful of detectives watched and followed (and likely bugged) Whitey for the rest of the summer and made numerous observations about him for posterity:

  • He came and went at odd hours. 
  • He distributed illegal lottery tickets. 
  • Every day he visited the University Grille on Whalley Avenue in New Haven, a notorious underworld hangout.
  • Another regular hangout of his was the Waterside Social Club in West Haven, an illegal bar Whitey owned.

Since they never spotted the suspected triggerman in the Schuster slaying, after about two months they gave up and returned to New York.

No arrest was ever made in the murder of Schuster.
Joseph Profaci

Growing up in Bath Beach Whitey was arrested again and again for committing a grab bag of crimes. While working as a runner for a crew of bootleggers, he was nabbed in June 1929 for burglarizing a store and was sent to prison. In 1933, he was released and next arrested and sent back for hijacking a truckload of silk.

In 1938, he was released again and  sought seemingly legitimate work at a Brooklyn bakery. This was around the time that he was linked by informants to Murder Inc in FBI reports. While the clues are tantalizing, he has never been definitively linked to Murder Inc.

He was directly linked two two murders in the 1940s, and was believed to be behind 10 slayings in Brooklyn in the 1940s. Allegedly those murders were the reason Joseph Profaci gave Tropiano New Haven.