Copyright © 2013 by Dick Lehr and Gerard O’Neill

All rights reserved.

Published in the United States by Crown Publishers,
an imprint of the Crown Publishing Group,
a division of Random House, Inc., New York.
www.crownpublishing.com

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trademarks of Random House, Inc.

Library of Congress Cataloging-in-Publication data

is available upon request.

ISBN 978-0-307-98653-5
eISBN 978-0-307-98654-2

printed in the united states of america

Book design by Donna Sinisgalli

Jacket design by Kristen Haff
Jacket photographs: Inmate case file AZ-1428 (The
National Archives at San Francisco)

10 9 8 7 6 5 4 3 2 1

First Edition

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 8
The Informer : 19 5 6

Whitey in custody

The night of his arrest Whitey Bulger was taken to the Boston Police
Department’s downtown station on Milk Street, where he was ques-
tioned briefly. The next morning, instead of robbing the Cambridge
bank, Whitey was headed to federal court for his arraignment. The
news of his capture spread quickly, with Boston’s newspapers running
photographs of him in police custody, his hair the color of black shoe
polish. The FBI put out a story that agents had been hot on Whitey’s
trail for days and had the “Revere spot under surveillance for several
nights and when two agents sighted the suspect there they called for
reinforcements.” The account of the arrest was not accurate, but one
that accomplished two goals: it made the bureau look smart and all-
knowing and shielded the fact that Paul Rico’s informant was the one
who had alerted them to the Reef Café, setting off the Sunday night
scramble.
Maintaining the confidentiality of informants— covering for
them, in other words—was paramount to the FBI. For any law enforce-
ment agency the whole business of gathering intelligence from will-
ing crime figures is premised on secrecy. Without it, the flow of

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 84 | Dick Lehr and Gerard O’Neill

information would cease, likely replaced by the flow of blood as the

underworld closed in for the kill of a suspected informant.
The FBI valued informants as much as and probably more than
any other police agency. In fact, by the mid-1950s the FBI’s widespread
use of informants and its trafficking in secret intelligence had drawn
the attention of congressional committees seeking accountability. FBI
director J. Edgar Hoover pushed back hard. In January 1956 he issued
a statement in which, according to newspaper accounts, “the veteran
FBI chief again made clear that the informant’s cloak-and-dagger role
must remain sacrosanct.” Hoover fiercely defended the use of FBI in-
formers as essential in the nation’s fight against communism and
crime. Confidential informants, Hoover insisted, were “invaluable in
protecting national security.”
FBI agent Paul Rico was one agent who certainly understood the
value of informants in the context of crime fighting—as well as their
value to an agent’s career. The day after Whitey’s arrest, Rico was one
of ten agents who the top agent in Boston recommended should receive
an FBI “incentive award.” The boss in Boston asked FBI director
Hoover to award Rico a $250 bonus. Hoover did better than that— on
March 28 he wrote Rico a letter, marked “personal and confidential,”
to notify him that he was being promoted to the next grade in the FBI
ranks, effective immediately. Hoover cited Rico’s “superior accom-
plishments in connection with the Bank Robbery case involving James
J. Bulger Jr. and others.” He noted specifically that Whitey’s arrest was
“directly attributable” to Rico “developing a valued source of informa-
tion.” Then, showing privately what he stood for publicly, the FBI di-
rector hailed Rico’s overall work with informants: “I am also aware of
your noteworthy efforts in developing other sources of information,
and you are to be commended for results in this regard.” Hoover backed
up the accolades with a $965 raise, increasing Rico’s salary to $7,570
annually.

In court on March 5, 1956, the federal prosecutor handling Whitey’s

case called Whitey a flight risk and urged that bail be set high. “A vi-
cious person, known to carry guns, and by his own admission has an
intense dislike for police and law enforcement officers,” Assistant U.S.
Attorney Daniel H. Needham Jr. said. Needham got what he wanted.
Bail was set at fifty thousand dollars, a sum neither Whitey nor his

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 Whitey | 85

family had on hand. Under the circumstances, the best the Bulgers
could do was to line up an experienced and well-connected defense at-
torney, Theodore A. Glynn Jr. Glynn had served as a state representa-
tive during the early 1940s and later, in 1959, was appointed to the
Boston Municipal Court, eventually becoming chief justice of that
court.
Whitey had to sit tight behind bars, where he had plenty of time
to mull over his capture and to comprehend fully the reason for his
undoing: he’d been betrayed not just once but three times by fellow
criminal cohorts—first by Carl Smith, then by Ron Dermody, and
fi nally by Rico’s newly minted informant. The lessons would harden
in him like cement. From this moment on he would trust few and
demand supreme loyalty. Condemnation of informers reflected the
cultural values of his hometown Southie. His brother Bill later ad-
dressed this cultural truism. “We loathed informers,” Bill wrote later
in a memoir. “Our folklore bled with the names of informers who
had sold out their brethren to hangmen and worse in the lands of our
ancestors.”
But actions despicable in others Whitey saw differently when it
came to himself. He was facing a mountain of trouble—three armed
robberies in three states. It was not a case of being wayward in front of
the juvenile court, or of facing an assault charge in the district court in
South Boston. This was not a disciplinary board in the Air Force or the
local courts in Montana. Whitey had fallen hard, and he knew it. The
FBI had him—all because he was ratted out. Faced with the prospect of
spending a virtual lifetime behind bars, he had to do something to try
to improve his lot.
Whitey Bulger became an informer. He might tell himself he was
not the first to break rank. Carl Smith held that honor, and Whitey
might rationalize ratting on Smith as tit-for-tat. Indeed, there exists in
the crime world a maxim that ratting on a rat does not constitute rat-
ting. But it’s a pretzel logic informants usually adopt to justify their
betrayal. Criminals who refuse to talk under any circumstances,
known as the truly “stand-up guys,” dismiss the maxim as spin and
rank hypocrisy.
Besides, FBI records reveal Whitey did more than inform on his
informer Carl Smith. He admitted first that, yes, he robbed three banks
and, yes, Carl Smith and Ron Dermody were with him to rob the bank

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 86 | Dick Lehr and Gerard O’Neill

in Pawtucket. The FBI report noted: “Bulger, after his apprehension,

cooperated with the Bureau to the extent of admitting his participation
in three bank robberies. He reduced his admissions to signed state-
ments and named his two accomplices in the Rhode Island bank rob-
bery.” Whitey’s information thus far was helpful confirmation of what
the FBI already knew; indeed, Smith was in custody and, thanks to
Smith, so was Dermody. But then came key information that Whitey
refused to include in any signed statement, meaning he did not want to
create a permanent written record. Whitey informed the FBI that Rich-
ard Barchard was with him while robbing the Indiana bank, and he
also said that William L. O’Brien was his partner in the Melrose, Mas-
sachusetts, holdup. Or, as the FBI report stated: “Bulger orally admitted
who his accomplices were in these bank robberies” (emphasis added).
Finally, Whitey delivered girlfriend Jacquie McAuliffe to FBI agent
Rico and his colleagues; Whitey “persuaded [her] to cooperate with
the Bureau,” the FBI report noted. Based on his information and “as a
result of her cooperation, process was obtained for Bulger’s accom-
plices, Richard R. Barchard, in the robbery of the Woodmar Branch of
the Hoosier State Bank, Hammond, Indiana, November 23, 1955, and
for William L. O’Brien, in the robbery of the Highlands Branch of the
Melrose Trust Company, Melrose, Massachusetts, November 18, 1955.”
Conduct considered anathema in Southie became, for Whitey, a
cold calculation. No right or wrong, no moral judgment was attached;
rather, informing was a strategy taken for self-preservation, which,
after all, was what mattered most. And it was a secret hidden in records
off-limits to the public.

The FBI picked up William L. O’Brien on May 3. They found him in

Burlington, Vermont, and he was arrested at a construction site work-
ing as a bricklayer. O’Brien was returned to Boston the next day, where,
like Whitey, he was held on fifty thousand dollars’ bail. Ten days later,
on May 14, the FBI arrested Richard Barchard in Rodeo, California.
When they found Barchard he was earning $1.69 an hour working as a
laborer at American Radiator and Standard Sanitary Corporation.
He’d also proposed marriage to a seventeen-year-old girl he’d met in
Rodeo. The marriage would have been illegal; though separated, he
was still married to Dorothy Barchard. But laws against polygamy, like
most laws, were apparently not going to stop Barchard.

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 Whitey | 87

Both men folded quickly. Barchard described how he came to

admit his culpability in a handwritten statement he prepared for court
several years later. He said that following his arrest in California the
FBI agents asked him about “his activities, particularly with reference
to his association with one James Bulger Jr. and their alleged activities
at Hammond, Indiana, on or about November 23, 1955.” Barchard said
that initially he denied any involvement with Bulger. The agents, he
wrote, “then told him that one James Bulger, who it was alleged par-
ticipated in the bank robbery, had informed agents of the FBI at Boston
Massachusetts that he (Barchard) had robbed the said bank with the
said James Bulger.” Just as troubling, wrote Barchard, he “was further
told that the information Bulger had given them indicated that his wife
had been involved in the instant robbery and that if he insisted on
causing more trouble and expense than he had already caused, that his
wife would be prosecuted for complicity in the robbery.” Barchard said
he was warned that if he fought the charges, federal prosecutors would
seek the stiffest sentence possible. Barchard decided to end it there. He
agreed to plead guilty.
Back in Boston, Whitey’s case proceeded quickly following his
confession. One thing he wanted in return for a guilty plea was to have
the three bank robbery cases concluded together in Boston, not sepa-
rately in the three jurisdictions. “After making the aforementioned ad-
missions, Bulger indicated that he desired to plead guilty to the
robberies of these banks and that he desired to plead in Boston, Mas-
sachusetts,” the FBI report stated. Whitey was working every angle—a
possible home court advantage, where disposing of all three at once in
Boston might help shorten the length of his prison term. Whitey got
his wish; on May 23 the local federal court received papers from pros-
ecutors in Indiana saying they agreed to the proposal that the Ham-
mond bank robbery be handled in Boston. In addition, prosecutors
ultimately left Jacquie McAuliffe alone; she was never charged in con-
nection with the Indiana holdup or for harboring a fugitive during the
manhunt. In fact, her identity and role were kept out of the public eye;
the closest reporters got to her was the mention in a few articles that
during the manhunt, Whitey had traveled with a girlfriend.
The federal judge in Boston, George C. Sweeney, scheduled Whit-
ey’s sentencing for June 21. To assist him in considering a sentence, a
federal probation officer went to work assembling a “Presentence

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 88 | Dick Lehr and Gerard O’Neill

Report.” The confidential report of more than a dozen pages—for the

judge’s eyes only—was based on court, school, and other records, along
with interviews with Whitey’s parents and Whitey himself. It included
Whitey’s full criminal record, going back to his first arrest as a juvenile,
and contained such sections as “Narrative of Offense,” which was a
detailed account of the bank robberies. The report noted that Whitey
now claimed he was broke, having spent his way through more than
twenty-five thousand dollars in cash. “The proceeds from these hold-
ups have been spent on lavish living in Florida, where he went with his
girlfriend.” There was another section called “General Reputation,” in
which the probation department reported to the judge that Whitey’s
reputation was “exceedingly poor,” that he began breaking the law as a
juvenile, and that “he has been in considerable trouble as a law violator
ever since.
“During his early years he was very difficult to handle at home and
in school. His companions were far from a good influence upon him.
He chose to associate with known thieves and ex-convicts and has no
desire to work.”
In the section “Personal History,” the report summarized his trou-
bled time in school, which he quit after the ninth grade and where “he
had very little interest in school work and failed practically all his sub-
jects.” The report mentioned his service in the Air Force, where he “at-
tended school and received a high school diploma,” and the fact that
afterward he was not interested in finding “legitimate work” but in-
stead resumed associating “with known criminals.”
The section “Family History” was based in part on information the
Bulgers provided, including the family lie that Whitey’s father’s age was
more than a decade younger than his true age. It included as well James
J. Bulger Sr.’s own past brushes with the law: “arrested for assault with
a revolver in Roxbury, case dismissed. He also has previous arrests
for drunkenness.” Whitey’s mother was described as a “housewife,”
brother Bill, twenty-two, “a student in his sophomore year at Boston
College,” sister Jean, twenty-eight, a widow working as a secretary; sis-
ter Carol, eighteen, living at home and a secretary at Carney Hospital;
brother John, or “Jackie,” seventeen, living at home and working at the
Boston Traveler newspaper; sister Sheila, twelve, living at home and at-
tending a Catholic high school. In the section “Family Situation,” this
point was emphasized: “It may be noted that during his formative years

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his father was very strict with him and on occasions beat him severely.
This, however, had very little effect on him as he continued to misbe-
have in the community.”
Whitey was described as physically fit, who denied “use of drugs,
but admits drinking heavily at times.” His IQ was a very solid 113,
“which indicates above average intelligence.” In addition, “he has al-
ways been a leader.” For all Whitey’s intelligence and leadership poten-
tial, however, the probation officer did not hold out much hope. Whitey
Bulger, the report stated, was “a rather serious law violator to have at
large in the community. He would not hesitate to use a gun.” It pre-
dicted: “The prognosis for future behavior in society is poor.”
Beyond those conclusions, the report included a statement that a
reader might easily overlook amid the many stronger assertions. The
passage, in the section “Mental Condition,” stated that Whitey “knows
the difference between right and wrong; his actions have been in ac-
cord with his own choosing.” The comment, at first reading, seemed
benign enough— certainly nowhere near as eye-catching as if the com-
ment on his mental condition had called him a maniac or some other
category of madman. But the observation actually might have been the
most insightful in the entire report. It was a line that Dr. Hervey Cleck-
ley, the leading thinker of that era about psychopaths, could have
authored— essentially restating what he and other researchers of psy-
chopathy considered to be the core characteristic of a psychopath,
namely, a person without conscience, a person who knew the differ-
ence between right and wrong but who did not care one iota.
That, the report was saying in a nutshell, was Whitey.

In terms of the city’s crime news that spring and summer, Whitey
Bulger’s first major collision with the criminal justice system was over-
shadowed by buildup to the sensational trial of eight men in the Brink’s
case—what the media were billing “the most dramatic trial of the cen-
tury.” In January, as the six-year statute of limitations was about to
expire in the 1950 holdup, the FBI had made the bombshell announce-
ment that it had solved the robbery by turning one of the original sus-
pects into a cooperating witness. Joseph J. “Specks” O’Keefe had
“sung,” as the newspapers put it, and named the eight defendants slated
to go on trial later in 1956. The spring and early summer featured the
final pretrial wrangling between attorneys, and then, on August 6,

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 90 | Dick Lehr and Gerard O’Neill

amid the 1950s version of a media circus, jury selection began. “Be-
cause of the notoriety attached to the $1,219,000 holdup of Brink’s Inc.,
in Boston’s North End on Jan. 17, 1950, the eyes of the nation—indeed,
the world, will be focused on the seventh floor, spacious, oak-paneled
courtroom,” the Boston Globe reported in its sprawling front-page cov-
erage, which included photographs of the accused, the judge, and a
drawing depicting the courtroom’s layout. Jury selection lasted nearly
a month and the trial itself spilled into early October, climaxing with
the jury’s unanimous guilty verdicts against all eight defendants.
Whitey did not yet have that kind of marquee power. The day of his
reckoning, Thursday, June 21, turned out, coincidentally, to be St.
Aloysius’s feast day, a celebration held on the date of the death, at age
twenty-three, of the patron saint of youth and innocence. St. Aloysius
died in 1591 while caring for the sick during a plague in Rome. He was
remembered for writing about entering the priesthood: “I am a piece of
twisted iron; I entered religion to get twisted straight.”
Whitey Bulger was brought to federal court—no St. Aloysius
he—under overcast skies, with a steady drizzle and fog encircling the
city by mid-afternoon. Bill Bulger, who would soon study law at Bos-
ton College Law School after earning his undergraduate degree, was
seated in the courtroom listening as each side made its recommenda-
tions to Judge Sweeney. Prosecutor Daniel Needham, citing Whitey’s
weaponry and the multiple robberies, called Whitey a “professional
bank robber” who should be sent away for twenty-five years. Whitey’s
lawyer, Theodore Glynn, urged the judge to impose a much shorter
sentence, which would offer a ray of hope to his client for a life after
prison. Glynn reminded the judge that Whitey had demonstrated
“some penitence” and had cooperated since his arrest. But the guilty
plea to all three robberies was all that was known publicly about the
extent of Whitey’s cooperation. Few in the courtroom that day, except
for the judge, the lawyers, and, likely, brother Bill, knew the rest of the
story—that Whitey and Jacquie McAuliffe’s informing had led to the
apprehension of Barchard and O’Brien.
Once he’d taken it all in, Judge Sweeney sentenced Whitey to a
twenty-year term in federal prison. The newspapers dutifully covered
the hearing. So. Boston Man Gets 20 Years for 3 Holdups, was the
headline in the Boston Globe, atop a brief account tucked in a single
column on the front page. No story questioned the sentence, not at

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twenty years. For the first time in his life, Whitey was going to prison.
The hammer had dropped hard—a twenty-year sentence was bad.
But was it? In the context of three convictions, and compared to his
fellow robbers, Whitey actually did better than could have been ex-
pected. Whitey got a ten-year sentence for the Pawtucket holdup; his
partner Dermody, who, like Whitey, had confessed, was sentenced to
seventeen years. Whitey got a ten-year sentence for the Indiana holdup;
his partner Barchard, who also confessed, was sentenced to twenty
years. Only William L. O’Brien, Whitey’s partner in the Melrose
holdup, got a lesser sentence. Whitey got a ten-year sentence for Mel-
rose while O’Brien got an eight-year sentence. Prosecutor Needham
had joined O’Brien’s defense attorney and recommended leniency for
the Dorchester bricklayer and father of four who had no prior criminal
record. Judge Sweeney agreed: “It’s too bad that O’Brien with his intel-
ligence would get himself into a situation where he became a potential
killer.” Then there was the other informer, Carl Smith. Like Whitey,
Smith got a sentence of twenty years in Indiana, in a package settle-
ment of his crimes.
The bottom line for Whitey: he was sentenced to ten years for each
robbery, but the sentence became a twenty-year term because the judge
ruled that only one of the ten-year sentences was to run consecutively
with the others. Meanwhile, as said, Dermody got seventeen years for
his role in a single robbery; Barchard got twenty years for his role in a
single robbery. On its face, Whitey’s sentence was bad, but it might
have been far worse if not for his “cooperation.” Neither Whitey nor
Bill ever discussed publicly the impact Whitey’s informing had on
Judge Sweeney’s sentence. Whitey’s informing was buried for a half
century in government records. The only remark Bill Bulger ever made
about his brother’s day in federal court was a reference in his later
memoir to Judge Sweeney being “a strict but fair man.” With the ben-
efit of the fuller context, however, Bill Bulger’s observation connotes an
appreciation that things could have gone much worse for his brother.

The skies were blue and clear but the air was thick and the temperatures
climbed into the eighties on the day, Thursday, July 19, 1956, that
twenty-six-year-old Whitey Bulger arrived at the Atlanta Penitentiary
to begin his long stretch of hard time. The drive to the prison took
him to the outskirts of the city, through some quiet residential

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 92 | Dick Lehr and Gerard O’Neill

neighborhoods and, finally, to the entrance of the largest of the

thirty-one penal institutions operated by the Federal Bureau of Prisons.
The Atlanta Penitentiary was immense. “Stone and steel,” one of
Whitey’s fellow prisoners wrote in the inmate magazine about first see-
ing the complex. “A giant among buildings. You think: it looks like a
hospital. It looks like a morgue. It looks like hell, it looks like anything
you want it to look like rather than what it is, a prison.” The U.S. mar-
shal led Whitey, handcuffed and in shackles, up the fifteen marble
steps to a steel door, where under the gaze of a guard watching from a
tower, Whitey shuffled into the prison that held about 2,600 prisoners.
Inside, Whitey was handed over to a prison guard and the marshal
got a receipt certifying delivery, “exactly the same as a wholesaler of
meat gets from a butcher accepting a large side of beef,” an inmate
wrote. Whitey got his first shakedown, with a guard going through his
hair, his pockets, and his shoes. He was then led through a seemingly
endless maze of secured doors, down a hallway, and up a set of stairs to
the Records Office, drawing looks and stares from guards and other
inmates he passed along the way.
At such a moment it did not matter that he had managed, by turn-
ing into an informant, to cut himself a break in the potential punish-
ment for three armed bank robberies. That fact would serve only as
cold comfort on the very first day of a twenty-year sentence. Prison was
the end of the line, whether one year or twenty. Whitey was entering a
world where he would be vulnerable in the extreme—unmoored and
without the power and self-determination so central to his personality.
The closest thing he had seen to what he now faced was the Air Force,
and he had bucked frequently against its regimentation. Inmate arti-
cles in the prison magazine often mentioned the primal fear every new
arrival felt—no convict, no matter his history, personality, or crimes,
was exempt. There was simply no preparation for being caged.
Seated in the Records Office, Whitey obediently faced another
round of questions, all part of being processed into the institution. His
criminal records and his sentencing information were put into his
“jacket.” His fingerprints were taken, his hair was cut, and he was or-
dered to remove his clothes, which were put in a box. Then it was bend
over, straighten up, and take a shower. He was given a physical: his
height was five feet ten and weight was 149 pounds. Noted in his medi-
cal report were marks on the fist he led with when fighting: “several

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 Whitey | 93

small scars on knuckles of right hand.” The medical form also noted he
was missing some teeth, and it concluded that Whitey was in “general
good health” and ready for “regular duty.”
Whitey was ordered to get dressed in a loose-fitting pair of cover-
alls, and a photograph was taken to insert into his jacket. The mug shot
showed Whitey, his hair closely cropped, unsmiling. It seemed he was
trying to project a glare. But the result looked more vacant than tough.
And with the crew cut he seemed so young. In all, Whitey looked more
like a shell-shocked teen than a hardened criminal.

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