The criminal businesses of Boston mobsters

The federal trial of James “Whitey’’ Bulger provided an inside look at how organized crime operates, makes money, and handles people who get in the way. Their business enterprises range from extortion and loan sharking to robbery and gambling.

Now another Mafia associate, Enrico Ponzo, has been convicted of racketeering after spending 17 years on the lam working as a rancher in Idaho.

Take a look at how some of the most feared crime figures in Boston history made their money.

Enrico Ponzo

Path to illicit profits: Extortion, loan sharking, narcotics distribution

Ponzo is a reputed member of La Cosa Nostra, who spent 16 years on the run raising cattle in Idaho, according to prosecutors. He was convicted on Nov. 20 of racketeering, including an attack on mobster Francis P. “Cadillac Frank’’ Salemme in Saugus in 1989.

James ‘Whitey’ Bulger

Path to illicit profits: Extortion, drug dealing, loan sharking, bookmaking

As the head of the Winter Hill Gang, James “Whitey’’ Bulger allegedly ran a criminal enterprise from 1972 to 2000 in which he made money by extorting from bookmakers, drug dealers, and businessmen; and laundered his criminal profits through real estate transactions, according to testimony at his trial.

Stephen ‘The Rifleman’ Flemmi

Path to illicit profits: Extortion, drug dealing, loan sharking, bookmaking

Stephen “The Rifleman” Flemmi, testified in July at Bulger’s trial that his relationship with the South Boston gangster was “strictly criminal.’’ He described their criminal activities as bookmaking, loansharking, and extortion.

Carmen ‘Cheese Man’ DiNunzio

Path to illicit profits: Extortion, bribery

DiNunzio is a former reputed New England Mafia underboss. He is serving a six-year sentence for bribing an undercover FBI agent posing as a state official to try to win a $6 million contract on the Big Dig. He also operated a cheese shop in the North End.

In 2009, he admitted to extorting $500 a month from a North End bookmaker, who was forced to pay the mob to stay in business.

Anthony L. DiNunzio

Path to illicit profits: Extorting Rhode Island strip clubs and adult entertainment businesses for protection payments

Anthony is the younger brother of Carmen DiNunzio. He became the acting boss of the New England branch of the Mafia in 2010, according to Rhode Island State Police Superintendent Stephen O’Donnell.

DiNunzio is currently serving a 6½-year federal prison sentence for his role in a plot to extort protection payments from strip clubs and other adult entertainment businesses in Rhode Island. The charges stemmed from an indictment that resulted in the imprisonment of eight leaders, underbosses, members, and associates of the New England branch of La Cosa Nostra. Included in that list is former New England Mafia boss Luigi “Louie’’ Manocchio.

The Brinks robbers

Path to illicit profits: The Brinks robbery in the North End

On Jan. 17, 1950, seven robbers made their way through several locked doors and up to the second floor where they hustled over $1.2 million in cash and more than $1.5 million in securities from Brinks employees in the North End.

At the time, it was the largest heist in US history and dubbed “The Perfect Crime.’’ The robbers and several others involved were all tied to organized crime and were later caught and charged with the robbery.

Peter Limone

Reputed path to illicit profits: Illegal gambling

Peter Limone spent 33 years in prison for a gangland murder he didn’t commit, but had brushes with the law after his release and receipt of a $26 million settlement for the wrong done to him. He pleaded no contest in 2010 to charges that he oversaw a crime ring that generated hundreds of thousands of dollars in gambling profits.

Limone avoided jail time, but was ordered to stay away from known Mafia figures. Prosecutors have said Limone is a member of La Cosa Nostra.

During the investigation into the gambling case, authorities found that Limone collected more than $178,000 since his release from prison in 2001 even though he didn’t have a steady job, prosecutors said. Police also seized $26,000 from his home during a raid in 2008.

Gennaro ‘Jerry’ Angiulo

Path to illicit profits: Various racketeering activities

The New England mob underboss ran Boston’s rackets from the 1960s until the early 1980s. Authorities tapped his North End headquarters, leading to his trial on federal racketeering charges. He spent 24 years in prison, but died a free man at age 90 in 2009.

Donato ‘Smiley’ Angiulo

Path to illicit profits: Various racketeering activities

The former New England Mafia capo regime was the brother of Gennaro Angiulo. Surveillance video entered into evidence during Bulger’s trial included footage of Donato Angiulo and Bulger together at the Lancaster Street Garage in the North End in 1980.

He, his brothers Gennaro and Francesco, a mob accountant, were convicted of federal racketeering charges in 1986. Another brother, Michele, was convicted of illegal gambling. Donato Angiulo died in 2009 at age 86.

Vincent Ferrara

Path to illicit profits: Racketeering, extortion, gambling

A federal judge reduced the former Mafia captain’s sentence after finding evidence of government misconduct in his case. Ferrara pleaded guilty to racketeering and other charges in 1992, but US District Judge Mark L. Wolf also found he admitted to a 1985 murder that he probably didn’t commit.

Francis ‘Cadillac Frank’ Salemme

Path to illicit profits: Various racketeering activities

The former boss of the New England branch of La Cosa Nostra has been in the witness protection program since 2003. As Mafia boss, he forged ties to Bulger and was especially close to Flemmi. Salemme was included in the 1995 federal racketeering indictment that also named Bulger and Flemmi.

Howie Winter

Path to illicit profits: Fixing horse races, alleged extortion

Winter preceded Bulger as the head of the Winter Hill Gang. He took over the gang from Buddy McLean, who was killed in the Irish mob wars in the 1960s. Winter was later indicted, along with 20 other people, on charges that he fixed horse races. In September, he and another man were indicted on charges that they attempted to extort $35,000 from two businessmen.

Mark Rossetti

Path to illicit profits: Usury, extortion, selling heroin

Mark Rossetti, once a feared captain in the New England Mafia, is serving 12 years in prison for running a violent criminal enterprise across Eastern Massachusetts. He admitted to lending money at exorbitant interest rates to a gambler and for using threats to collect gambling debts for bookies.

Angelo ‘Sonny’ Mercurio

Path to illicit profits: Stealing securities, extortion

The Mafia soldier helped the FBI land the first-ever bugging of a mob induction ceremony and acted as a liaison between the Boston branch of the Mafia and the Winter Hill Gang. He became an informant after authorities gathered enough evidence to indict him and others on extorting a couple of elderly bookmakers. He died in 2007 at age 70 in Arkansas.

James ‘Buddy’ McLean

Path to illicit profits: Running numbers, loan sharking, truck hijackings, theft

James “Buddy’’ McLean led the Winter Hill Gang during its bloody war with the McLaughlins in Charlestown. He was gunned down by the Charlestown crew in the 1960s.

Harry ‘Doc’ Sagansky

Path to illicit profits: Number pools, horse race rackets

The Brookline resident was among 23 suspects accused of being a part of a multimillion-dollar number pool and horse race racket in 1943.