For decades, the name James “Whitey” Bulger was synonymous with organized crime in Boston.
He was a feared underworld figure, the longtime leader of Boston’s Winter Hill Gang, a secret FBI informant, and eventually one of the most wanted fugitives in America.
His story included murder, extortion, organized crime, corruption, betrayal, a 16-year international manhunt, a dramatic arrest in California and, ultimately, a violent death inside a federal prison.
But behind the legend was a very real criminal enterprise—and victims whose lives were permanently changed by it.
This fall, Murders in Massachusetts LIVE will take audiences behind one of the most infamous chapters in Boston crime history with two men uniquely positioned to tell the story.
Boston 25 investigative reporter Bob Ward and retired FBI Supervisory Special Agent Rich Teahan, authors of Face to Face with Whitey Bulger: An FBI Agent’s Account of Capturing and Debriefing Boston’s Most Notorious Gangster, will appear LIVE on stage.
EXPERIENCE THE STORY LIVE
Murders in Massachusetts LIVE
Saturday, November 7, 2026
Chelmsford Center for the Arts
Beginning at 6:30 PM
Tickets are limited.
GET TICKETS & EVENT INFORMATION → MURDERSINMA.COM/LIVE
WHO WAS WHITEY BULGER?
James Joseph Bulger Jr. was born on September 3, 1929, in Massachusetts.
He grew up in South Boston and would ultimately become one of the most powerful and feared organized-crime figures in New England.
Bulger became closely associated with the Winter Hill Gang, a criminal organization operating in the Boston area. By the 1970s and 1980s, federal authorities later alleged that his organization was involved in a wide range of criminal activity, including extortion, loan-sharking, gambling, narcotics trafficking and murder.
Bulger’s power was not based simply on intimidation.
For years, he also maintained an extraordinary—and deeply controversial—relationship with the FBI.
That relationship became one of the defining scandals of his story.
THE WINTER HILL GANG
The Winter Hill Gang emerged as a major force in Boston organized crime during the latter half of the twentieth century.
Despite the name, its influence extended well beyond Somerville’s Winter Hill neighborhood.
Bulger eventually became one of the organization’s dominant figures and operated primarily from South Boston.
His reputation grew alongside stories of intimidation, violence and ruthless enforcement.
At the height of his influence, Bulger had become one of Boston’s most notorious underworld figures.
Yet law enforcement’s relationship with him was far more complicated than the public knew.
WHITEY BULGER AND THE FBI
Perhaps the most disturbing aspect of the Bulger story was his relationship with federal law enforcement.
Bulger became a high-level FBI informant, supplying information concerning rival organized-crime figures.
The relationship was intended to help federal authorities dismantle other criminal organizations.
Instead, it became a staggering example of what can happen when the lines between law enforcement and criminal informants become dangerously blurred.
Bulger received information from corrupt FBI personnel and, according to investigators, was protected while continuing to operate his own criminal enterprise.
His longtime relationship with former FBI agent John Connolly became central to the scandal.
Connolly had grown up in South Boston and later became Bulger’s FBI handler.
The relationship ultimately raised devastating questions:
How much did federal authorities know?
How much did Bulger receive in return for his information?
And did an arrangement intended to fight organized crime actually allow one of Boston’s most dangerous criminals to become even more powerful?
The Bulger case remains one of the most extraordinary chapters in the history of the FBI.
A REPUTATION BUILT ON FEAR
Bulger’s mythology became so large that fact and folklore sometimes became difficult to separate.
What is not in dispute is the seriousness of the crimes eventually proven against him.
When Bulger finally stood trial in federal court, prosecutors presented a sweeping case describing years of racketeering, extortion, violence and murder.
In 2013, a federal jury convicted Bulger on 31 criminal counts.
Jurors found that prosecutors had proven his involvement in 11 murders.
He was ultimately sentenced to two consecutive life sentences plus five years.
THE FBI INFORMANT WHO BECAME ONE OF THE FBI’S MOST WANTED
The contradiction was almost unbelievable.
A man who had once secretly provided information to the FBI eventually became one of the agency’s most notorious fugitives.
By 1994, authorities were preparing to indict Bulger on federal racketeering charges.
But Bulger learned that authorities were closing in.
He fled.
The warning that helped him escape was later linked to his former FBI handler, John Connolly.
What followed was one of the most famous fugitive investigations in American history.
16 YEARS ON THE RUN
Whitey Bulger disappeared for more than a decade and a half.
His ability to avoid capture became part of his legend.
He used aliases.
He moved around the country.
He traveled with his longtime companion, Catherine Greig.
And year after year, law enforcement continued searching.
Bulger was eventually placed on the FBI’s Ten Most Wanted Fugitives list, becoming Fugitive #458.
At one point, the reward for information leading to his arrest reached $2 million.
For years, his name appeared beside some of the most wanted criminals and terrorists in the world.
THE SEARCH FOR CATHERINE GREIG
Investigators eventually changed strategy.
Rather than focusing exclusively on Bulger, the FBI launched a highly publicized campaign aimed at locating Catherine Greig.
Greig had remained with Bulger throughout much of his life as a fugitive.
The campaign focused on characteristics that acquaintances might recognize—including her appearance and personal habits.
The strategy worked.
A member of the public provided information that helped authorities identify the couple’s location in California.
CAPTURED IN SANTA MONICA
On June 22, 2011, the 16-year search finally ended.
Bulger and Greig were living in an apartment in Santa Monica, California, not far from the Pacific Ocean.
Bulger was 81 years old.
Federal agents used a ruse to lure him from the apartment and arrested him without a major confrontation.
Inside the residence, investigators discovered weapons, cash and false identification.
Authorities reportedly recovered more than $800,000 in cash and approximately 30 firearms from the apartment.
After 16 years on the run, Whitey Bulger was finally in custody.
FACE TO FACE WITH WHITEY BULGER
Capture was only part of the story.
After decades of evading authorities, Bulger was finally sitting across from federal investigators.
Among those tasked with interviewing him was FBI Supervisory Special Agent Rich Teahan.
That extraordinary encounter forms the heart of Face to Face with Whitey Bulger: An FBI Agent’s Account of Capturing and Debriefing Boston’s Most Notorious Gangster, written by Teahan and Boston investigative journalist Bob Ward.
Teahan recounts what happened when federal investigators finally had the opportunity to question the man they had spent years pursuing.
What was Bulger like face to face?
What did he say once the chase was over?
What did investigators want to know?
And what did his answers reveal about one of America’s most notorious organized-crime figures?
Their book provides a rare perspective from someone who was actually inside the room.
HEAR THE STORY FROM THE MEN WHO KNOW IT
On Saturday, November 7, Bob Ward and Rich Teahan will appear together at Murders in Massachusetts LIVE at the Chelmsford Center for the Arts.
This isn't simply a discussion about Whitey Bulger from people who studied the story afterward.
Rich Teahan helped investigate and interview him.
Bob Ward spent decades reporting on major crime and justice stories in Massachusetts.
Together, they will take the audience inside the investigation, Bulger’s capture and the extraordinary experience of sitting across from one of Boston’s most infamous criminals.
Audience members will also have an opportunity to hear about their book and participate in a live Q&A.
SEE BOB WARD & RICH TEAHAN LIVE
Murders in Massachusetts LIVE
Saturday, November 7, 2026
Chelmsford Center for the Arts
Starts at 6:30 PM
RESERVE YOUR SEAT → MURDERSINMA.COM/LIVE
THE TRIAL OF WHITEY BULGER
Bulger returned to Massachusetts to face federal prosecution.
His trial began in Boston in June 2013.
Prosecutors presented evidence describing an expansive criminal enterprise that had operated for decades.
The allegations included racketeering, extortion, narcotics trafficking, money laundering, weapons offenses and numerous murders.
The proceedings also reopened old wounds surrounding Bulger’s relationship with the FBI.
After weeks of testimony, the jury returned its verdict in August 2013.
Bulger was convicted on 31 of 32 counts.
The jury found him responsible for participating in 11 murders.
In November 2013, a federal judge sentenced him to two consecutive life sentences plus five additional years.
THE VICTIMS BEHIND THE WHITEY BULGER STORY
The mythology surrounding Whitey Bulger can sometimes overwhelm the human cost of his crimes.
Movies, books, headlines and decades of Boston folklore transformed Bulger into an almost larger-than-life figure.
But organized crime is not mythology.
It leaves victims.
Families lost loved ones.
People lived under intimidation and fear.
Communities were affected by violence, corruption and distrust.
Any examination of Whitey Bulger's life must remember that the fascination surrounding his story exists alongside tremendous suffering caused by the criminal enterprise surrounding him.
BLACK MASS AND THE WHITEY BULGER LEGEND
The Bulger story eventually entered popular culture.
The 2015 film Black Mass, starring Johnny Depp as Bulger, introduced another generation to the story of the South Boston crime boss and his relationship with corrupt members of the FBI.
But Hollywood could only capture part of the story.
The actual history—particularly the law-enforcement failures, the informant relationship, the manhunt and what happened after his capture—is far more complicated.
And at Murders in Massachusetts LIVE, you'll hear part of that history directly from someone who experienced it.
GET YOUR TICKETS → MURDERSINMA.COM/LIVE
THE DEATH OF WHITEY BULGER
Whitey Bulger's life ended violently.
On October 30, 2018, the 89-year-old Bulger was transferred to USP Hazelton, a federal penitentiary in West Virginia.
Within hours of arriving, he was attacked and killed by fellow inmates.
The circumstances surrounding his placement at the prison generated intense scrutiny.
A later Justice Department Inspector General investigation found numerous management and operational failures surrounding the transfer and placement of Bulger, although investigators reported finding no evidence that federal prison employees intentionally arranged his death.
The killing provided one final violent chapter in a life already defined by organized crime, murder and betrayal.
THE WHITEY BULGER TIMELINE
1929
James Joseph Bulger Jr. is born.
1950s–1960s
Bulger serves time in federal prison and later becomes increasingly involved in Boston organized crime.
1970s–1990s
Bulger rises within the Winter Hill Gang and becomes one of the most powerful organized-crime figures in Boston.
1970s
Bulger develops a relationship with the FBI as an informant.
1994
With federal charges approaching, Bulger disappears.
1999
He is placed on the FBI's Ten Most Wanted Fugitives list.
June 22, 2011
After approximately 16 years on the run, Bulger is captured in Santa Monica, California.
2013
Bulger stands trial in federal court in Boston.
August 12, 2013
A jury convicts him on 31 counts and finds his involvement proven in 11 murders.
November 2013
Bulger receives two consecutive life sentences plus five years.
October 30, 2018
Hours after arriving at USP Hazelton in West Virginia, Bulger is killed by fellow inmates.
FROM SOUTH BOSTON TO AMERICA’S MOST WANTED
Few criminal stories have intersected with Boston history the way Whitey Bulger's has.
He was simultaneously:
A feared organized-crime leader.
An FBI informant.
A fugitive.
A symbol of institutional corruption.
One of America's most wanted men.
A convicted murderer.
And eventually, a murder victim himself.
His story exposed extraordinary failures inside institutions entrusted with enforcing the law and left Massachusetts confronting uncomfortable questions about how one criminal organization gained so much power.
Those questions—and the stories behind them—continue to fascinate the country decades later.
GO FACE TO FACE WITH THE WHITEY BULGER STORY
This November, Murders in Massachusetts brings that story to the stage.
Join Boston 25’s Bob Ward and retired FBI Supervisory Special Agent Rich Teahan for an extraordinary live conversation about Whitey Bulger, the FBI investigation, the years-long search that ended in California and what happened when investigators finally sat face to face with Whitey Bulger.
You'll hear stories that cannot be captured by a movie or a headline—from someone who was actually there.
MURDERS IN MASSACHUSETTS LIVE
Saturday, November 7, 2026
Chelmsford Center for the Arts
6:30 PM
Featuring:
Bob Ward
Boston 25 investigative reporter and award-winning journalist
Rich Teahan
Retired FBI Supervisory Special Agent
Co-authors of:
Face to Face with Whitey Bulger: An FBI Agent’s Account of Capturing and Debriefing Boston’s Most Notorious Gangster
Plus additional live conversations, audience Q&A, special guests and more from Murders in Massachusetts.
ONE NIGHT. ONE STAGE. AN EXTRAORDINARY PIECE OF BOSTON CRIME HISTORY.
GET TICKETS & COMPLETE EVENT DETAILS → MURDERSINMA.COM/LIVE
Early Bird Tickets are available for a limited time.