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The FBI Agent Who Secretly Ran Boston's Mob
Oct 1, 2025
For 20 years, FBI Special Agent John Connolly lived a double life—bureau golden boy by day, mob associate by night. This explosive documentary reveals how Connolly turned the FBI into a protection service for Boston's most dangerous crime boss, Whitey Bulger, leading to 19 deaths and the biggest corruption scandal in FBI history. From his childhood in South Boston to his current prison cell, we expose how one agent weaponized federal resources for organized crime, corrupted an entire FBI office, and destroyed countless lives while earning commendations. Based on court documents, FBI files, and witness testimony, this investigation uncovers the terrifying ease with which the line between cop and criminal can disappear. Was Connolly always corrupt, or did his relationship with Bulger slowly poison him? How many other agents might be playing both sides right now? Share your thoughts: Could this level of corruption happen again in today's FBI? The FBI Agent Who Secretly Ran Boston's Mob 🔔 Subscribe for more investigations into law enforcement's darkest secrets 📺 Next: The DEA Agent Who Built a Cartel Empire -~-~~-~~~-~~-~--~-~~-~~~-~~-~--~-~~-~~~-~~-~- ⚠️ Content Disclaimer: This video is created for educational and informational purposes only. We do NOT glorify, promote, or encourage any form of criminal activity. All visuals, audio, and materials used in this video are either: ✔ Created using AI tools, or ✔ Sourced from royalty-free platforms with valid licenses. No copyrighted content belonging to others has been used without permission.
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0:00
Boston, 1975.
0:03
An FBI agent sits in a dimly lit Irish
0:06
pub, sharing drinks with the city's most
0:09
dangerous gangster. But this isn't an
0:12
undercover operation. It's a business
0:14
meeting. For the next 20 years, special
0:18
agent John Connelly would feed FBI
0:20
secrets to James Whitey Bulier, creating
0:24
the most corrupt partnership in law
0:26
enforcement history. By the time anyone
0:29
realized what was happening, 19 people
0:32
were dead, and Connelly had helped build
0:34
a criminal empire worth $50 million. So,
0:38
get ready to dive into the twisted story
0:40
of how America's premier law enforcement
0:41
agency became the protection service for
0:44
Boston's most ruthless crime boss. The
0:46
truth is, we don't know much about what
0:48
drove John Connelly to cross the line.
0:51
Connelly was two different people,
0:54
recalled retired FBI agent Robert
0:56
Fitzpatrick. In the office, he was the
0:59
golden boy. Commendations, perfect
1:02
reports, rising star. On the streets of
1:05
Souy, he was something else entirely. He
1:09
was one of them. John Joseph Connelly
1:12
Jr. was born on August 1st, 1940 in
1:16
Boston's Old Harbor Housing Project in
1:19
South Boston. souy to locals. This
1:23
wasn't just a neighborhood. It was a
1:25
fortress of Irishamean identity where
1:28
outsiders were viewed with suspicion and
1:31
loyalty to your own was the highest
1:34
virtue. The Connelly family lived in a
1:37
three- room apartment where heat came
1:40
from a coal stove and privacy was a
1:43
luxury nobody could afford. Young John
1:47
grew up in the shadow of neighborhood
1:49
legends, particularly the Bulger family.
1:52
William Billy Bulier was the golden
1:55
child, brilliant, ambitious, destined
1:58
for politics. His older brother, James,
2:01
known as Whitey, was different. A
2:04
small-time thief with dead eyes and a
2:07
reputation for calculated violence. John
2:10
Connelly, 8 years younger than Whitey,
2:13
watched both brothers with fascination.
2:17
But there was a problem that would
2:18
define Conny's entire life. He was
2:22
caught between two worlds. The insular
2:26
tribal world of Souy where he belonged
2:28
and the larger world of law and order
2:31
where he aspired to matter. His father,
2:34
Gway John, worked as a toll collector
2:38
and preached the importance of civil
2:40
service. His mother pushed education as
2:43
the path out of poverty. Yet every day,
2:47
young John saw that real power in Souy
2:51
didn't come from badges or degrees. It
2:54
came from fear and loyalty. The pivotal
2:58
moment arrived in 1958 when Connelly was
3:02
beaten by older kids from a rival
3:04
housing project. According to
3:06
neighborhood law, Whitey Bulier
3:09
intervened, sending the attackers
3:11
running. Whether this actually happened
3:14
or became myth through retelling,
3:16
Connelly internalized a dangerous
3:19
lesson. Whitey Bulier was his protector,
3:23
his hero, the man who kept him safe when
3:26
the system couldn't. Therefore, when
3:29
Connelly graduated from Boston College
3:31
in 1962 and joined to the FBI in 1968,
3:36
he carried with him a fundamental
3:38
conflict. He swore an oath to uphold the
3:42
law, but his deepest loyalty remained to
3:45
the code of Souy. You never forget where
3:48
you came from and you never betray your
3:51
own. Conny's FBI career began in San
3:56
Francisco and New York where he
3:58
distinguished himself infiltrating
4:00
organized crime. He had a gift for
4:03
developing informants, particularly in
4:06
Irish-American communities. His
4:09
superiors noticed his ability to
4:11
navigate the criminal world while
4:13
maintaining his cover as a straight
4:15
arrow agent. By 1973,
4:19
he engineered a transfer back to Boston,
4:22
claiming he wanted to be closer to his
4:24
aging parents. But Connelly had other
4:26
plans. The Boston FBI office in the mid
4:30
1970s was in crisis. The Italian mafia,
4:34
particularly the Angulo family,
4:36
controlled gambling, lone sharking, and
4:39
much of the city's corruption. The Irish
4:42
gangs, including Whitey Bulges Winter
4:45
Hill gang, were seen as secondary
4:47
threats. The FBI needed informants
4:50
inside these organizations, but their
4:53
traditional methods weren't working.
4:56
Nevertheless, Connelly proposed a
4:58
radical solution. On a September evening
5:01
in 1975,
5:03
Connelly arranged a meeting with Whitey
5:06
Bulier at Wallist Beach in Quincy. No
5:09
wires, no backup, no official record.
5:13
Just two kids from Souy having a
5:15
conversation. I told him we could help
5:18
each other. Connelly would later
5:20
testify. He could give us information
5:22
about the Italians, and in return, he'd
5:25
have some breathing room to operate.
5:28
Yet, this wasn't the standard informant
5:30
relationship. Connelly wasn't recruiting
5:33
Bulger. He was partnering with him. The
5:36
information would flow both ways. Bulger
5:40
would provide intelligence on the
5:41
Italian mob, while Connelly would warn
5:44
him about investigations,
5:46
identify other informants, and eliminate
5:49
his competition through targeted
5:51
prosecutions. The deal was formalized
5:54
with Bulger being designated a top
5:56
echelon informant, the FBI's highest
5:59
classification for criminal sources. On
6:02
paper, this looked like a masterful law
6:05
enforcement coup. In reality, Connelly
6:08
had just handed the keys to the FBI's
6:11
kingdom to one of Boston's most
6:13
dangerous criminals. However, the
6:16
corruption went deeper than simple
6:18
information exchange. Connelly began
6:21
living beyond his FBI salary, expensive
6:24
dinners, vacation homes, diamond rings
6:27
for his girlfriend. He explained it as
6:29
smart investments, and family money. But
6:31
the truth was simpler. Bulier was paying
6:34
him. Not just with occasional envelopes
6:36
of cash, but with something more
6:38
valuable. Access to a criminal empire's
6:40
resources. The arrangement transformed
6:43
Bulger from a regional gang leader into
6:45
Boston's most powerful crime boss. With
6:48
Conny's protection, he eliminated rivals
6:51
with impunity. When the DEA prepared to
6:54
arrest Bulger for drug trafficking,
6:56
Connelly intervened, claiming Bulger was
6:59
too valuable an informant to lose. When
7:03
Massachusetts State Police got close to
7:05
Bulger's gambling operations, Connelly
7:08
warned him about the impending raids.
7:10
Still, Connelly maintained his cover
7:13
brilliantly. He produced a steady stream
7:16
of intelligence reports, carefully
7:19
edited to make Bulger appear invaluable
7:22
while hiding his most serious crimes. He
7:25
cultivated other FBI agents, bringing
7:28
them into Southeast Irish bars,
7:31
introducing them to the culture, slowly
7:34
compromising them with small favors and
7:37
shared secrets. Connelly was like a
7:39
virus in the bureau, explained former
7:42
federal prosecutor Fred Wshack.
7:45
He didn't just corrupt himself, he
7:47
corrupted the entire Boston office.
7:50
Agents who should have been
7:51
investigating Bulger were instead
7:53
protecting him, and most didn't even
7:56
realize it. The relationship's peak came
8:00
in the early 1980s when Connelly used
8:03
Bulger's information to bug Jarro and
8:06
Yulo's headquarters, resulting in the
8:09
destruction of Boston's Italian mafia.
8:12
The operation made Connelly a hero
8:15
within the FBI, earning him
8:17
commendations and promotions, but it
8:20
also eliminated Bulger's only real
8:22
competition,
8:24
giving him monopolistic control over
8:27
Boston's underworld.
8:29
Therefore, by 1985, a terrible symbiosis
8:32
had developed. Bulier needed Connelly to
8:35
protect him from law enforcement, and
8:37
Connelly needed Bulger to maintain his
8:40
reputation as the FBI's most successful
8:43
organized crime agent. They met
8:46
regularly at appliance stores, beach
8:49
parking lots, and private homes. They
8:52
exchanged gifts at Christmas. Their
8:54
children knew each other. The line
8:56
between agent and criminal had
8:58
completely dissolved, but cracks were
9:00
forming in the facade. Other law
9:03
enforcement agencies began noticing
9:05
patterns. How their investigations into
9:08
Bulger always seemed to fail at crucial
9:11
moments. How witnesses against him
9:14
disappeared or recanted. How Bulier
9:16
always seemed to know when surveillance
9:19
was active. The DEA, Massachusetts State
9:22
Police, and even other FBI agents
9:25
started asking uncomfortable questions.
9:28
The beginning of the end came in 1988
9:32
when FBI agent John Morris, Conny's
9:35
supervisor and fellow corrupt agent,
9:38
began cooperating with investigators out
9:41
of guilt and fear. Morris revealed the
9:44
scope of the corruption, not just
9:47
information sharing, but active
9:49
participation in criminal enterprises.
9:53
He described dinners where Connelly and
9:55
Bulier planned criminal strategies like
9:58
business partners. Yet Connelly was
10:00
protected by his reputation and
10:02
connections. He had allies throughout
10:04
the bureau who couldn't believe their
10:06
golden boy was corrupt. When questioned,
10:10
he had explanations for everything. the
10:12
money, wise investments, the meetings
10:15
with Bulger, developing intelligence,
10:18
the failed investigations,
10:20
bad luck, and smart criminals.
10:23
Nevertheless, the situation became
10:27
untenable in 1990 when Connelly retired
10:30
from the FBI with full honors and
10:33
accommodation from the director. He
10:36
immediately took a high-paying job with
10:38
Boston Edison, arranged by William
10:41
Bulier, Whitey's brother, who had become
10:44
president of the Massachusetts Senate.
10:47
Even in retirement, Connelly continued
10:50
to protect his old partner. The full
10:53
truth emerged only after Bulier fled
10:56
Boston in 1994,
10:58
tipped off by Connelly about an
11:01
impending indictment. As investigators
11:04
dug into how Bulier had evaded capture
11:06
for so long, they uncovered the
11:09
systematic corruption that Connelly had
11:11
orchestrated,
11:13
FBI files were filled with false
11:15
reports. Witnesses described Connelly
11:19
actively participating in criminal
11:21
planning. Financial records showed
11:24
unexplained wealth flowing through
11:26
Conny's accounts. However, the most
11:29
damning evidence came from Bulger's
11:32
other associates who facing life
11:34
sentences began revealing the true
11:37
nature of the FBI Bulger relationship.
11:41
They described Connelly not as a handler
11:43
running an informant, but as a full
11:45
partner in Bulger's criminal enterprise.
11:48
He didn't just protect Bulger, he helped
11:51
plan murders, identify targets, and
11:54
cover up crimes. Steven the Rifleman
11:57
Flemmy Bulier's partner provided
11:59
devastating testimony.
12:01
John Connelly was as much a member of
12:03
our organization as anyone. He just
12:06
happened to carry an FBI badge. In 2002,
12:11
Connelly was convicted of rakateeering
12:14
and obstruction of justice, but the
12:17
worst was yet to come. In 2008, he was
12:21
convicted of seconddegree murder for his
12:24
role in the 1982 killing of John
12:26
Callahan, a business executive who could
12:29
have implicated Bulger and Connelly in
12:31
another murder. The Golden Boy of the
12:33
FBI was sentenced to 40 years in prison,
12:36
effectively a life sentence for the
12:38
68-year-old. Still, Connelly maintains
12:40
his innocence, claiming he was a
12:43
dedicated agent who did what was
12:44
necessary to fight organized crime. In
12:47
letters from prison, he writes about
12:49
being betrayed by the bureau he served,
12:52
about being scapegoed for institutional
12:54
failures. He presents himself as a
12:57
victim of changing times and shifting
13:00
politics. But the evidence tells a
13:03
different story. Connelly didn't just
13:06
cross the line between law enforcement
13:08
and crime. He erased it entirely. He
13:11
weaponized the FBI's resources for
13:14
criminal purposes, turning the bureau
13:17
into a tool for Bulger's empire. He
13:20
corrupted other agents, destroyed
13:22
investigations, and contributed to
13:25
multiple murders. The damage extended
13:28
far beyond individual crimes. Conny's
13:32
corruption undermined public trust in
13:34
law enforcement, particularly in
13:36
Boston's Irish-American community, where
13:39
he was once seen as a hero. Families of
13:42
Bulger's victims sued the FBI for
13:46
enabling their loved ones murders. The
13:48
bureau itself underwent massive reforms,
13:52
implementing new oversight procedures
13:54
for informant relationships. Therefore,
13:57
the question remains, was John Connelly
14:00
always corrupt, waiting for the right
14:03
opportunity, or did his relationship
14:05
with Bulger slowly poison him? Each
14:08
small compromise leading to larger
14:11
betrayals. Former FBI agent Robert
14:14
Fitzpatrick believes it was both.
14:17
Connelly came to the bureau with divided
14:20
loyalties. Bulier just gave him
14:22
permission to be who he always was. The
14:26
psychological profile of Connelly
14:28
reveals a man torn between identities.
14:32
He wanted the respect and authority of
14:35
being an FBI agent, but he also craved
14:38
the street credibility and tribal
14:40
loyalty of Souy. Bulger offered him
14:43
both. He could be the successful federal
14:45
agent while secretly being one of the
14:48
neighborhood boys who made good. Yet
14:51
perhaps the most disturbing aspect of
14:53
Conny's story is how many people enabled
14:56
it. FBI supervisors who ignored warning
15:00
signs because Connelly produced results.
15:03
Agents who suspected something but
15:05
stayed quiet to protect their careers.
15:08
Politicians who benefited from the
15:10
Bulger family's influence. The
15:12
corruption wasn't just individual. It
15:14
was institutional.
15:16
Today, John Connelly sits in a Florida
15:19
prison scheduled for release in 2039
15:22
when he would be 99 years old. He spends
15:26
his time writing appeals, maintaining
15:28
his innocence, and corresponding with a
15:31
shrinking circle of supporters who still
15:33
believe he was a hero betrayed by the
15:36
system. Meanwhile, the FBI has tried to
15:40
move past the Connelly scandal,
15:42
implementing strict new guidelines for
15:44
handling informants. But the shadow
15:47
remains. Every time an agent meets with
15:50
a criminal informant, the ghost of John
15:53
Connelly is in the room, a reminder of
15:56
how easily the line between cop and
15:59
criminal can blur. The victim's families
16:03
have never received full justice. Many
16:06
of Bulger's murders might have been
16:08
prevented if Connelly had done his job
16:11
instead of protecting a killer. The
16:13
exact number of deaths attributable to
16:15
Conny's corruption will never be known,
16:18
but prosecutors estimate at least a
16:21
dozen people died because of information
16:24
he provided to Bulger. So, what do you
16:27
think? Was John Connelly a good agent
16:29
who got too close to his informant? Or
16:32
was he always a criminal who found the
16:34
perfect cover in the FBI? Could this
16:37
happen again with today's oversight? Or
16:41
are there other connalies out there
16:42
right now playing both sides? Drop your
16:45
theory in the comments. I read every
16:47
single one. Subscribe for the next
16:50
investigation into the dark corners
16:52
where law enforcement and organized
16:55
crime intersect.