The Worcester Mafia and Gambling

From Frank Iaconi to Carlo Mastrototaro, organized gambling was the mainstay of the Worcester Mafia.

By Steven R. Maher

The January 1950 marriage of Worcester Mafia boss Frank Iaconi’s daughter was spectacular, a scene right out of the Godfather. “The wedding took place in true millionaire fashion in Miami,” the Providence Journal reported. “The reception that followed at the Roney-Plaza Hotel, one of the city’s finest, even made a few not easily excited Miamians stare.”

Among those present at the extravaganza was Massachusetts Lieutenant Governor Charles F. “Jeff” Sullivan, the Mayor of Worcester from 1946-1950. Until Jeff Murray in 2006, Sullivan was the last Worcester resident to be elected to state wide office.

Sullivan’s friends begged reporters not to mention that Worcester’s most prominent politician was attending the nuptials of the daughter of Worcester’s most prominent Mafioso. “He [Sullivan] just slipped down here for a little vacation, and it might prove embarrassing,” one pleaded.

Also present was Worcester Police Lieutenant William V. Massei. In 1940 Massei was appointed head of the vice squad, charged with the suppression of gambling in Worcester. Iaconi – described in Senate testimony as “the head of the gambling rackets in Worcester Massachusetts” – had no problems from Massei, who told the media, “There is no gambling or lottery in Worcester.” Iaconi, the man who headed the Worcester gambling rackets and Massei, the cop in charge of suppressing the Worcester gambling rackets, even owned summer homes in Westerly, Rhode Island “..within shouting distance of one another…”

Besides Lieutenant Governor Sullivan, there was another, unrelated Sullivan present: former Ward 3 councilman Philip F. Sullivan, who in 1946 was sued along with Iaconi for $57,300 by a die maker, who claimed he had been swindled out of his life savings in an Iaconi gambling den. The event had sparked a reform movement, spear headed by Worcester Telegram owner Harry G. Stoddard, which led to the adoption of Plan E government in Worcester. Philip F. Sullivan freely posed for photographers at the Iaconi wedding, praising the gangster as “a millionaire groceryman.”

Present too were other gangland figures. Frank Costello, the “Prime Minister” of the underworld and

America’s top racketeer, sent a personal emissary to the wedding.

Surveying this scene of splendor and opulence, basking in the glow of representatives of Worcester’s political establishment present to pay him homage, beaming at the respect shown by his underworld peers, Frank Iaconi must have commented to himself on his good fortune. Thirty years earlier, an immigrant fresh off the boat, Iaconi had labored in a public works project, digging ditches for a new sewer system,
“Iaconi literally rose from a job in a sewer gutter to a position of great power in the second largest city in Massachusetts,” recounted the Providence Journal.

Enormous gambling profits

Iaconi could afford such a pageant because of the enormous profits from his gambling rackets. Gambling would be the bread and butter of the Worcester Mafia for half a century, providing a healthy diet of cash.
In 1950 the Providence Journal published a lengthy expose about organized crime in Worcester, based in part on information from a member of the Worcester Mafia. The story described a “tri-city” criminal combine with cadres in Boston, Providence, and Worcester. This expose, and rackets expert Virgil W. Peterson’s testimony to the Senate Kefauver Committee, provides a basis of understanding how the Worcester Mafia grew from a bootlegging syndicate into a gambling cartel. Iaconi was front and center in both developments.
“He [Iaconi] dropped his pick and shovel in the 20s to take part in the gambling war that hit Worcester,” said the Journal. “From that he emerged with a small piece of the rackets and the reputation of being a pretty handy trigger-man.”

More profitable was Prohibition, the criminalization of alcohol, begun in 1920 and ended in 1933. Called “the noble experiment”, Prohibition made the Mafia. The end of Prohibition forced the mob to diversify into other rackets, one of which was gambling. Worcester followed this national model.
Iaconi formed a relationship with Worcester native Raymond L.S. Patriarca, a powerful Providence based mobster who in the 1950s became the Godfather of the New England Mafia. “Patriarca and Iaconi were associated together during rum-running days,” testified Peterson. “Iaconi worked for the Patriarca gang as a Providence-Worcester agent. Booze was run between the two cities.” In this capacity “Iaconi ran booze between the two cities for 50 cents a gallon and usually hauled about 300 to 400 gallons a trip.”

“Iaconi then left the bootlegging racket and began operating beano games, then horse betting, and then numbers,” said Peterson. This was no small time operation. Said the Journal: “His [Iaconi’s] rackets milk millions of dollars from the city’s economy each year. His numbers agents float in every industry, barroom, and public gathering place. At least half a dozen horse parlors operate brazenly not far from city hall, and about 20 others do business throughout the rest of the city.”

Worcester’s mob boss put his money to work suborning law enforcement. Massei at Iaconi’s daughter’s wedding was the tip of the iceberg. Worcester police detectives and officers provided security for Iaconi’s gambling parlors; cops actually stood guard at card games. When state police raided Iaconi gambling operations in Fitchburg, the bookies were tipped off and evaded arrest.

Symbolizing the relationship between law enforcement and mobsters was the attendance at the 1946 wedding of Iaconi’s son of no less a personage than the Sheriff of Worcester County. Six City Councilors (then called Councilmen) were also present. The occasion allowed the media to comment on Iaconi’s access to black market goods: “Even though many wartime rationing restrictions were still in effect, no one seemed to question the source of nearly 1000 steaks or the sugar that was dumped into the five-layer, 153 pound wedding cake.” This image, of politicians and cops gorging themselves on contraband steaks and cake at a Mafioso wedding, seems like a scene out of a mob comedy movie.

Important terminal

”Iaconi’s Worcester monopoly is an important terminal in the tri-city combine because of its immunity from police interference,” continued the Providence Journal. “Besides pouring hundreds of thousands of dollars into the syndicate’s reciprocal layoff system, Iaconi provides the only safe haven for ‘hot’ racketeers who merit syndicate protection. A racketeer on the lam from Providence, Boston, or any other city is assured of an undisturbed existence in Worcester if he has the O.K. of the syndicate, the former Worcester gangster reports.”

“When you say Iaconi is a shooting man, we laugh,” the defector from the Worcester Mafia remarked. “He doesn’t have to do any shooting. If someone comes into town that’s hot, he just tells the police to lay off. If someone comes in who’s not wanted, he picks up the phone and tells the cops where to get him.”
Iaconi’s control of Worcester also made it a safe place for Mafia leaders to meet. According to one published report, some 200 syndicate leaders, including Frank Costello, met at the Sheraton Hotel in Worcester in 1950.

Some believed that city officials had struck a Faustian bargain with Iaconi. One urban legend had it that Iaconi, in exchange for running his gambling operations without police interference, kept large-scale narcotics and large-scale prostitution out of Worcester. Credence to this “unholy procedure” was given by a May 1950 Worcester Telegram editorial.

“But when, throughout the years, top officials here have asked about gambling protection, the answer has been that there was an ‘arrangement’ with Iaconi which was to Worcester’s advantage,” read the editorial. “For through him, they said, Worcester was shielded from invasion by racketeers from Boston, Providence, and elsewhere who might have otherwise would have muscled in on the Worcester field, but were kept out by the squire of Shrewsbury Street. So Iaconi, we are asked to believe, was protecting Worcester.”

Rackets committee

Iaconi had such a strangle hold over Worcester that it took a United States Senate Committee to bring him down. Worcester police never succeeded in arresting Iaconi. In 1943 Massachusetts Attorney General Robert T. Bushnell conducted raids in Worcester and arrested Iaconi for promoting a lottery. Iaconi got off with a slap on the wrist: a $5,000 fine and a two-year suspended sentence.

The Kefauver Committee was established by the U.S. Senate to investigate organized crime, and named after committee chairman Senator Estes Kefauver. After hearing testimony in 1950, Kefauver himself said the committee would examine Iaconi’s tax returns. This triggered an Internal Revenue Service investigation of Iaconi, who was indicted on five counts in February 1953 of failing to pay a total of $217,875 in taxes on $350,000 in rackets revenue. The indictment alleged Iaconi had tried to wash clean his gambling receipts through front corporations in Worcester.

“The government is understood to have based its case before the Grand Jury on evidence that allegedly showed Iaconi had funneled illegitimate funds through legitimate enterprises,” Worcester’s daily newspaper reported. “It was reported that East Side Package Store, 129 Shrewsbury Street, and Central Wholesalers Grocery Inc., 76 East Worcester Street, Worcester, were cited before the Grand Jury as evidence of Iaconi’s legitimate enterprises.”

Massei, the vice squad commander who attended the 1950 wedding of Iaconi’s daughter, was indicted by the same grand jury for failing to report $74,739 in taxable income over five years.
In July 1954 Iaconi pled guilty to one count and served eleven months in federal prison in Danbury Connecticut. Not long after being released from prison Iaconi died of natural causes.

Carlo Mastrototaro

Fast-forward thirty years to the 1980s and things were remarkably the same, with different players. Carlo Mastrototaro was the boss of the Worcester Mafia with corrupt cops protecting his enterprises, albeit a tad subtler than in Frank Iaconi’s days.

Mastrototaro had risen high in mob circles. After Boston based underboss Gennaro J. Angiulo was jailed, Patriarca reportedly promoted Mastrototaro to underboss, the second in command of the New England Mafia.
But in the early1980s Mastrototaro had a determined adversary who emerged from the same geographic and ethnic terrain as the Worcester Mafia: District Attorney John A. Conte.

It is hard to find anyone in the Worcester media with a good word to say about John Conte. He made reporters’ lives difficult. Obsessed with keeping the District Attorney’s office nonpolitical, Conte made himself almost completely unavailable for comment on crime stories. Legend had it that one Worcester Telegram reporter had programmed his computer to automatically type into stories that Conte had no comment. Conte’s rare press conferences or comments inspired Diane Williamson to dub Conte “The Phantom”.

Conte was elected state senator in 1962. In 1973 two Worcester Lodges of the Sons of Italy gave Conte their achievement award. As a state senator whose district included Worcester’s east side, Conte must have crossed paths with Mafiosi at public events in certain neighborhoods. That didn’t stop Conte from prosecuting them years later as District Attorney. Given the damage done to Italians’ reputation by the Mafia, there is some historical justice in the prominent role played by an honest Italian-American like Conte in a concerted effort to disrupt the Worcester Mafia.

“Operation Big League”

Past law enforcement efforts to dismantle organized crime failed because Mafiosi were prosecuted as individuals for solitary acts. RICO, the Racketeer Influenced and Corrupt Organizations Act, which was to prove so effective against criminal syndicates, was in its infancy. Conte approached the Worcester Mafia as an organization, which had to be taken apart from top to bottom, from Mastrototaro at the heights to the low level street operators. Conte was on the cutting edge of jurisprudence, using a RICO-style approach before RICO itself became fashionable.

Conte was convinced that the mob was dealing narcotics.

“I think there has been one myth that has been prevailing in the Commonwealth of Massachusetts for the past few years: that organized crime is not into drugs,” Conte told reporters at a press conference. “I think we can dispel that and say point blank that wherever we find gaming and organized crime, we positively seem to find drugs also.”

In October 1980 the investigation got underway. Code-named “Operation Big League”, it began with electronic surveillance in locations around Worcester County between February and August 1981. 500 cassettes of audiotapes, each sixty to ninety minutes long, were compiled recording bookmaking, drug deals, and other sundry crimes.

In August federal, state, and local police raided 17 locations in Worcester, Clinton, Saugus, Springfield, Agawam, Brookline, and Concord. “All aspects of organized crime, from gaming and drugs to extortion, porno shops and prostitution – you name it, it was all uncovered in one fashion or another in this investigation,” said Conte.

The evidence from the raids and the electronic surveillance was brought before a grand jury and 44 people were charged:

• Mastrototaro and four other men were indicted for running an extensive gambling operation. Operating out of a location on Green Street in Worcester, the enterprise took bets, ran a lottery by phone at several locations in Worcester and one in Clinton. Counting those indicted in later investigations, this network may have had over seventy operatives throughout Worcester County.

• Mastrototaro was charged in connection with the theft of $45,000 worth of pornographic videos, which were to be sold by Mastrototaro’s pornography store United Books on Main Street in Worcester. (See following story.)

• A drug network was exposed selling cocaine, marijuana, Valium and other controlled substances. Mastrototaro was not indicted on any drug related charges, but some of the men charged with helping Mastrototaro running a gaming syndicate were also charged with running the drug operation.

• To complete the analogy with Frank Iaconi’s era, three Worcester cops were indicted for conspiracy to sell cocaine and other defalcations. One of the cops was nicknamed “Security”, apparently for his efforts at safeguarding Mafia activities. All three later pled guilty to charges of trafficking cocaine.

“The main purpose [of Operation Big League] is to prosecute organized crime and bring to public attention the connection between drugs and gaming in organized crime operations,” Conte said at a press conference. “The public will know there are police agencies that want to bring down organized crime.”

As a result of intelligence developed from “Operation Big League”, two other large-scale prosecutions of organized crime later took place. One was “Operation Rackets” in June 1983, in which thirteen were charged with running a wagering network in the Leominster area. In March 1984 Conte obtained indictments in “Operation Underworld” against thirty-seven participants in a Worcester area gaming operation. A number of those indicted had east side addresses, and three had the last name Mastrototaro.

Carlo Mastrototaro was not indicted in “Operation Rackets”. By this time he had pled guilty to a number of “Operation Big League” charges and was sentenced to eighteen months in jail. In 1984 was convicted and sentenced to three years in prison for his part in a $1 million scheme to defraud 3,000 persons in a bogus travel agency scam.

Some conclusions

Organized gambling was long the lifeblood of the Worcester Mafia. Two conclusions can be drawn from this chronicle. First, modern technology -sophisticated electronic surveillance – is the best tool for penetrating and dismantling illegal, dangerous networks. Second, such gambling syndicates can only thrive in an atmosphere in which they are tolerated by a complacent or corrupted law enforcement.

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