Whitey Bulger's Girlfriend Sentenced to Additional 21 Months in Jail

A South Boston woman who spent 16 years on the run with one of Boston’s most notorious gangsters, James “Whitey” Bulger, was sentenced to spend another 21 months behind bars by a federal judge who called her longtime companion “a monster” not worthy of her “love and affection.”

Catherine Greig, 65, is currently serving an eight-year sentence for her role in helping Bulger escape and evade capture after he was tipped to a pending federal indictment by his rogueFBI handler in 1995. She wore a black sweater in court today, her white hair cut short, and smiled at her twin sister Margaret, who was in the courtroom, sitting across from the relatives of two Bulger murder victims.

The couple was captured in June 2011 living in a rent-controlled apartment near the Santa Monica Pier using the monikers Charles and Carol Gasko. Investigators found 30 high-powered weapons in the walls along with a stash of $822,000 in cash. Their bedroom was lined with bookshelves stocked with Bulger’s favorite mob books. Many featured him.

Today’s sentencing dealt with new federal criminal contempt charges stemming from what prosecutors called Greig’s “consistent, dogged and tireless” refusal to cooperate with a grand jury that continues to investigate who, if anyone, helped Bulger while he hid from authorities.

“The public has a right to know who else had a hand,” Assistant United States Attorney Mary Murrane argued. The government wanted the U.S. District Court Justice Dennis Saylor to sentence Greig for 37 months.

Greig’s defense attorney, Kevin Reddington, argued that the only crime his client was truly guilty of was falling in love with the wrong man and said the government was overzealously seeking to punish Bulger’s paramour because she refused to give up “her friends and family.”

“It is obvious that she is a kind, gentle woman who has literally done nothing bad in her life except fall in love with James Bulger and live with him for 16 years until his arrest,” Reddington told the court.

The judge was unmoved.

“Bulger is a monster," the judge said. “Ms. Greig is not remorseful. She is not apologetic. She is not trying to distance herself from Bulger. She is not inclined to change her behavior. She’s an adult she knows the rules. She brought this entirely upon herself."

As for “her only crime here is being loyal to Whitey Bulger, and that she loves him,” the judge added, “I hardly know what to say to that. It’s hard to imagine a less worthy object of love and affection.”

The judge did say he was swayed by Reddington’s argument that the government cut sweetheart deals with Bulger compatriots, including John Martorano, who confessed to killing 20 people but spent just 12 years behind bars.

In addition, a Defendant’s Sentencing Memorandum filed with the court “suggests that the ‘cross reference’ to Bulger’s crimes including murder and RICO violations is a gross due process violation. Greig has pled guilty to a crime of contempt; a non-violent offense.”

The memo also argues that “although the court may consider a virtually unlimited array of facts in determining a fair sentencing, it may not impose a sentence that exceeds the ‘substantively reasonable’ threshold.”

Bulger, 86, is serving a life sentence at a maximum-security prison after a 2013 conviction for 11 murders, racketeering and other federal charges.

Meanwhile, federal officials will hold a public auction in June at the Boston Convention and Exhibition Center to sell Bulger’s belongings seized from the Santa Monica hideout where the couple lived for more than a decade, part of a way to recoup some of the $25.2 million forfeiture judgment that came with Bulger’s conviction.

Profits from the weekend auction, which will include a coffee mug shaped like a rat, along with the $822,000 in cash found secreted in the walls of the hideout, will be divided among the families of 20 people killed by the gangster or his associates and among several people he extorted, according to court filings. The guns will not be sold at the event, slated to be held from June 24 to June 26, according to court records.

Those victims will also divide Bulger’s Social Security payments and any cash seized from safe deposit boxes and bank accounts uncovered in England and Ireland connected to Bulger.

James "Whitey" Bulger Trial


James "Whitey" Bulger didn't keep the drugs out of Southie, as the myth once held. He made millions as a drug dealer. He is an admitted racketeer. A leg-breaker. He extorted people and bribed corrupt FBI agents. He made millions. But he ain't no rat.  

Read why his trial has seemingly become about saving Bulger's street credibility rather than see him acquitted on 19 murder charges. 


James "Whitey" Bulger Trial 2013 

ABC News Coverage by Michele McPhee 

Eddie Connors shot dead after Whitey Bulger and Stevie the Rifleman opened fire on him. They lured him to the phone booth to wait for a call. 

Eddie Connors shot dead after Whitey Bulger and Stevie the Rifleman opened fire on him. They lured him to the phone booth to wait for a call. 

Debbie Davis Knew Too Much. Whitey Bulger Wanted Her Dead.  

Debbie Davis knew too much. And James “Whitey” Bulger wanted her dead. So did his FBI handler John Connolly, her longtime boyfriend Stephen “the Rifleman” Flemmi testified today. “He really wanted to kill her." “Did you agree with that?” asked federal prosecutor Fred Wyshak.

“Not at first,’’ Flemmi answered. “But then he gave me a litany of reasons.”

“He wasn’t too happy with my relationship with her. It affected our business,’’ Flemmi answered. “I bought her a Mercedes. I gave her a lot of money. She had a lot of jewelry. People start noticing that.”

“Why did that upset Mr. Bulger?” Wyshak asked. “Because that was drawing attention to me and to him,’’ Flemmi answered.

Boston Crime Lords Face Each Other For The First Time Since 1994 And F-Bombs Fly From the Stand - Stephen "The Rifleman" Flemmi and James "Whitey" Bulger Square Off In South Boston Court  

James "Whitey" Bulger warned Stephen "the Rifleman" Flemmi to get out of town Christmas week in 1994. He didn't listen and has spent the last 18 years in a federal WITSEC prison serving three life sentences plus 30 years. Did that lead Flemmi to snarl "Motherf---er!" to the defendant? Bulger responded in kind. "F--- you too!" 

whitey and stevie .jpg
What was your relationship with James Bulger?
— Fred Wyshak Federal Prosecutor
Strictly criminal.
— Stephen "the Rifleman" Flemmi

Stephen "Stippo" Rakes found dead Wednesday and Steven Davis, whose sister was murdered allegedly by Bulger and Stephen "The Rifleman" Flemmi.  

Stephen "Stippo" Rakes found dead Wednesday and Steven Davis, whose sister was murdered allegedly by Bulger and Stephen "The Rifleman" Flemmi.  

Witness Slated To Testify Against Bulger Found Dead At The Side of The Road

Stephen "Stippo" Rakes had no phone, no keys, no wallet...and no car when his body was discovered around 1:30 pm Wednesday on Mill Road in Lincoln, MA.  

old whitey .jpeg

One Bookie Came To Court In A Wheelchair. Another Brought His Oxygen Tank.   Once Feared Boston Mobsters Now Geriatric Gangsters In The Trial Of James "Whitey" Bulger.  

 Bulger's arthritic hands killed 19 people, prosecutors say.  The witnesses in Bulger's trial look more like they are headed for a Bingo game rather than the witness stand in the trial for Boston's most notorious mobster and reputed FBI informant. 


A South Boston Federal Courtroom Sounds Like A South Boston Street Corner as Wiseguys James "Whitey" Bulger and Kevin Weeks Trade F-Bombs. 

"YOU SUCK!"   James "Whitey" Bulger hissed at his former surrogate son Kevin Weeks. "F--- You, okay!" Weeks replied. Bulger repeated the phrase. Weeks responded with "What do you want to do?" The exchange forced the judge to her feet. It's the third time Bulger has sworn at a witness since his trial began last month 

white bulger and kevin weeks walk island .jpeg

 Whitey Bulger's "Surrogate Son" Testifies Against Him...Sets the Record Straight About the Takeover of Rotary Liquor Story That Became Bulger's Headquarters. 

“Sometimes in murders we handcuffed people,’’ Kevin Weeks told the court as the federal trial of a man he had long looked up to as a father figure, James “Whitey” Bulger, resumed after a five-day break. Knives, he added, were “for intimidation.”


Lawyers for James "Whitey" Bulger Want the Guns Seized at His Santa Monica Hideout Tossed Out.

Prosecutors called the guns vital to the case because the are "tools of the trade" for criminals. 

“He’s threatening me like you’ll do as I say or I’ll whack ya.”
— William Shea, a retired drug dealer from South Boston. Bulger trial Juy 2013

Drug Dealer Addresses his would-be killer as"Jim" as he described Whitey Bulger's Death Threat 

William Shea was a South Boston cocaine dealer. He made his money. He paid tribute to the neighborhood’s mob boss James “Whitey” Bulger and in 1986 he wanted out. There was one problem with that, Shea told the court today, Bulger didn’t want to let him out.

“I told him I’m not looking for a pension plan,’’ Shea told the court. “I put my ass, my butt, on that street for six or seven years, it was time for me to cash in.” Bulger said no, Shea recalled on the stand.

Dirty FBI Agent Gets Teary-eyed on the Stand Talking About the Man Murdered Because of Information He Shared With Gangsters  

John Morris never apologized to Brian Halloran's family for getting him killed...until today.  

'Whitey' Bulger Snickered When Witness Recalls Death Threat

Dick O'Brien was a Boston bookmaker. He learned the business from his father and learned it well. Dick O'Brien paid his debts fast and for that he got a lot of action. He had at least 30 agents under him at any given time and kicked up to the Italian mob.

That is until James "Whitey" Bulger summoned him to a meeting with his Winter Hill gang cronies, O'Brien testified today, recalling the conversation he had with the accused underworld boss in 1978.

Stuart Cahill/Boston Herald/Polaris

Stuart Cahill/Boston Herald/Polaris

James 'Whitey' Bulger Was a 'Hands on Killer,' Prosecutor Tells Jury

After Bucky Barrett talked, "this man over here, James Bulger, shot him in the back of the head,'' Assistant United States Attorney Brian T. Kelly said. And then, Bulger took a nap as others allegedly buried Barrett in the dirt cellar of the small house on E. Third Street in South Boston.

U.S. Marshals Service/AP

U.S. Marshals Service/AP

'Whitey' Bulger Hitman Says It 'Broke My Heart' to Hear Bulger Was FBI Informant

Confessed hitman, John Martorano, who has admitted killing 20 people, told a Boston court today that he was testifiying against his alleged former mob boss James "Whitey" Bulger because "it broke my heart" to discover Bulger was an FB I informant.


"Whitey" Bulger Hitman Says He Was a 'Vigilante... Not a Serial Killer'

Nightclub owner Richard Castucci had made a lot of mistakes in his life, but his biggest would prove to be too trusting of an FBI agent who grew up in South Boston.

“You were corrupt, weren’t you Mr. Morris?”
— Whitey Bulger defense attorney Hank Brennan asked longtime Boston FBI Supervisor John Morrise 2013
“The Boston FBI corruption goes all the way up to the DOJ – its either that they are responsible for what they did or they are not.”
— Hank Brennan, defense attorney, Bulger trial June 2013

Hitman Implicates Bulger in 13 Murders

Hitman John Martorano admitted on the stand today that he lied to his best friend before he shot him in the back of the head.

James 'Whitey' Bulger Drops F-Bomb in Court Again

For the second time this week accused Boston mobster James "Whitey" Bulger cursed under his breath at a witness testifying against him.

"You're a f***ing liar,"' Bulger, 83, was overheard saying from his seat at the defense table at former FBI supervisor John Morris.

Winter Hill Organization (ca. 1975-1980)

Winter Hill Organization (ca. 1975-1980)

'Whitey' Bulger's Alleged Bribes and Threat Recounted By Corrupt FBI Agent

Rogue FBI supervisor John Morris has testified that he gave his underling information that got a cooperating witness killed.

He slept with his secretary and let accused Boston mobster James "Whitey" Bulger buy her a plane ticket. When his wife tossed him out, Morris lived in another informant's apartment.

Guns secreted in a wall at Whitey's Santa Monica lair. Also recovered was $822,000 in cash. 

Guns secreted in a wall at Whitey's Santa Monica lair. Also recovered was $822,000 in cash.