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James 'Whitey' Bulger: The 25-million-dollar-man?

By Kristina Sgueglia and Lawrence Crook, CNN
updated 7:03 PM EDT, Fri September 20, 2013
James "Whitey" Bulger, the former head of Boston's Winter Hill Gang, evaded police for 16 years before his 2011 arrest with girlfriend Catherine Greig in Santa Monica, California. After a lengthy trial, Bulger, seen here in his booking photo from June 23, 2011, was found guilty on 31 of 32 counts -- including involvement in 11 murders. On November 14, 2013, Bulger was given two life sentences plus five years. Here's a look at some of the people tied to Bulger's life of crime: James "Whitey" Bulger, the former head of Boston's Winter Hill Gang, evaded police for 16 years before his 2011 arrest with girlfriend Catherine Greig in Santa Monica, California. After a lengthy trial, Bulger, seen here in his booking photo from June 23, 2011, was found guilty on 31 of 32 counts -- including involvement in 11 murders. On November 14, 2013, Bulger was given two life sentences plus five years. Here's a look at some of the people tied to Bulger's life of crime:
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Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
Who's who in the James 'Whitey' Bulger case
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STORY HIGHLIGHTS
  • During decades as a mob boss, 'Whitey' Bulger generated well over $25 million, feds say
  • Bulger was convicted in August of racketeering, extortion and money laundering
  • The jury ruled that he had participated in 11 murders
  • The government moves to seize Bulger's personal assets

(CNN) -- Who say's crime doesn't pay?

Boston's most infamous criminal, convicted mob boss James "Whitey" Bulger, generated well over $25 million in racketeering proceeds throughout his criminal career, according to paperwork filed in federal court.

Bulger's criminal escapades spanned more than two decades while he doubled as an informant for the FBI in Boston. The notorious mobster began building capital off his criminal empire around 1972 and continued until around 2000, 5 years after he went on the lam after being tipped off by his rogue FBI informant to a pending indictment.

A federal jury convicted Bulger in August on 31 counts of racketeering, extortion, and money laundering and ultimately ruled that Bulger participated in the murder of 11 people. He will be sentenced on November 13.

The evidence presented at trial established that "the proceeds from the Defendant's racketeering conspiracy totaled millions upon millions upon millions of dollars," according to the federal prosecutors' "motion of forfeiture" released on Friday.

The motion breaks down Bulger's spoils that were spelled out in testimony from gangsters, former associates, drug dealers, convicted felons, and extortion victims during more than 41 days of trial this summer.

David William Lindholm, a marijuana smuggler, testified he barely survived high-stakes a Russian-roulette-style drama when Bulger ordered one of his associates to fire a bullet past his head. Bulger then ordered his associate to load the chamber with one bullet.

"A bullet was put in the chamber it was spun and pointed at my head," said Lindholm. He lived to testify that Bulger extorted $250,000 from him.

Business entrepreneur Michael Solimando testified that Bulger put a gun to his gut, and threatened to kill his family. Solimondo, 64, described how at one meeting Bulger took a machine gun and "shoved it underneath the table, pointed at my stomach and my groin," and how he was forced to pay Bulger $400,000.

The ways of 'Whitey'

Another witness, real estate developer Richard Buccheri, used two fingers to mimic the a gun barrel as he described how Bulger "takes a shotgun off the table and sticks it in my mouth. Then he took it out, punched me in the shoulder and said, 'Richard you're a stand-up guy. I'm not going to kill you.'"

But then, Buccheri said, Bulger "puts a 45 to my head" and demands $200,000 in 30 days, "threatening to kill me and my family."

Convicted drug dealers testified that Bulger collected "rent" from criminal operatives, a crime tax that had to be paid to do drug business in South Boston during the Bulger era.

In 2011, Bulger was found hiding out in Santa Monica, California, with his girlfriend -- and with nearly $822,000 in cash, 30 guns, some loaded, and an assortment of knives and a Taser.

Before his conviction came down, Bulger waived his right to a forfeiture hearing. The government has moved to seize Bulger's personal assets that they say stemmed from a life of gambling and drug dealing, including jewelry, electronics, art, furniture, clothing and other items found in the Santa Monica apartment.

For now, Bulger is allowed to keep a National Hockey League Stanley Cup ring that he claims was given to him as a gift, according to paperwork.

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