Guest Blog Post -Michael Esslinger
James “Whitey” Bulger, 1428-AZ, was no ordinary criminal. When he arrived on Alcatraz in 1958, the soft-spoken Bulger known as simply “Jimmy” to fellow cons didn’t stand out as the man who would become the Al Capone of his era.
Whitey Bulger has been the subject of a variety of major Hollywood films and documentaries. Martin Scorsese used Bulger’s persona as the model for the central character in his film The Departed, the Academy Award winner for Best Picture in 2007. He later noted during an interview, “In no way do we say that Francis Costello, played by Jack Nicholson, is directly patterned after Whitey Bulger, but let me put it this way, we felt comfortable in the character; we felt comfortable in the situation, because we knew it to be true…
In the late 1970s, he became the principal figure of the Winter Hill gang, the preeminent Irish-American crime syndicate in the Boston area. He sustained at the top of Boston’s criminal underworld for nearly three decades without ever being charged for even a misdemeanor crime.
In bookstores, true crime sections are typically dominated with works chronicling his life and crimes and in movies he is depicted as a hands-on enforcer who ruled the streets of Boston and beyond. He grew-up in the tough South Boston housing projects and, as a youth, idolized the bigger than life Hollywood bad guys like James Cagney, Edward G. Robinson and George Raft. Bulger later commenting, “Those men were the heroes to kids my age in the Projects…
Despite the numerous books and movies on Bulger’s life, what’s often overlooked are the formative years he spent on Alcatraz closely watching mafia moguls like Mickey Cohen and Bumpy Johnson that he served time alongside on the Rock. For the young Bulger, Alcatraz was not only a front row seat to watching the highest stratum of crime figures and how they conducted themselves walking among peers, but also contributing to one of the greatest prison breaks of the 20th Century. His role in the famed 1962 escape of Frank Morris and the Anglin Brothers would become a training ground for understanding what it would take to successfully disappear while on the run from authorities.
Bulger’s path to Alcatraz started at an early age. At only 14, he was arrested and charged with larceny. By the 1950s, he had graduated to more serious crimes, then finally in 1955, Bulger would begin a series of bank robberies that would begin in Rhode Island, with Carl Smith who would also later serve time on the Rock as1238-AZ, and then later with crime partner Richard Barchard (1251-AZ), who together robbed the Hoosier State Bank in Hammond, Indiana, netting over $12,000 in cash. They followed a specific approach with each robbery. Holding a pistol in each hand as in the style of an old west outlaw, Bulger would hold aim on bank employees while Barchard scooped the cash into a bag and then both fled to a stolen getaway car that was driven by Barchard’s wife Dorothy. The car was driven to a nearby parking lot and then they switched into another car where Bulger’s girlfriend awaited them. A nationwide manhunt by law enforcement was launched to bring the men and their accomplices to justice. By the time Bulger was finally captured on December 2, 1955, in Miami, Florida, the heists had brought in more than $100,000 in cash.

37 blog post; Richard Barchard, 1251-AZ
Richard Barchard, 1251-AZ

Bulger received a 20 year sentence, and was initially sent to the United States Penitentiary at Atlanta, Georgia, in July of 1956. The years in Atlanta were tough with Bulger participating in medical trials for Malaria treatments and later the covert MK-Ultra LSD testing that would fall under public scrutiny for the brutality it imposed on human subjects. Prisoners received good time credits off their sentence for their participation. It was in Atlanta that he first met several convicts who he would later serve time alongside on the Rock.
In February of 1958, Frank Morris, brothers John, Clarence and Alfred Anglin who would later take part in one of the famed prison breaks in American history, were also in Atlanta and it was here they’d first met. Bulger had been plotting an escape, and in a report from the Associate Warden, he would indicate that in every escape plot they’d uncovered, Bulger had some part in the planning. Bulger had been involved in a failed escape along with another convict John Paul Scott who would serve time on Alcatraz and later make his own break attempt. An informant identified Bulger as having secured hacksaw blades from an officer, and despite harsh confinement in solitary, he refused to give up the identity. While serving time in solitary confinement, Bulger celled across from Frank Morris and the two spent countless hours in idle conversation. On October 21, 1959, Bulger’s official transfer order to Alcatraz was issued and he arrived less than a month later as 1428-AZ.

37 blog post; Bulger's official transfer order to Alcatraz.
Bulger’s official transfer order to Alcatraz.

Bulger’s first cell, C-145, was located along the main corridor of Broadway. It was here standing at the bars that he would meet Clarence “Joe” Carnes who passed along messages from several friends who had already made their way to the island. Carnes and Bulger were to become good friends during his tenure on Alcatraz. In December, he moved to the top tier of C Block to C-314 where he mostly remained for his years spent on the Rock. The upper section of C Block was a coveted area. It was on the top tier where prisoners could hear well in advance correctional officers ascending the stairs during routine and surprise inspections. The cells along this corridor faced the sprawling cement wall of D Block and those on the upper tier where Bulger lived had the brightest and warmest cells as the rays of bright sunshine gave warmth to an otherwise dismal landscape. Bulger read extensively from the Alcatraz library and loved many of the classics including the western adventure novels by Zane Grey.

37 blog post; Bulger's cell
Whitey Bulger’s main cell (C-314) on the third tier of C Block. The cell faced a sprawling cement wall, but was quiet with bright sunlight for reading, and offered reasonable privacy from patrolling guards along the flats.

On Alcatraz, Bulger held a variety of work roles, including working in Clothing Issue in the cellhouse basement and then in October of 1960, he took a job as part of the cellhouse maintenance detail. He mentored one new arrival, John Anglin, who was to later take part in one of the most famous prison breaks in American history.
Following his maintenance assignment, in December of 1960, he took a new job in the prison laundry working under an officer A.G. Bloomquist. Nicknamed “Bloomie” by fellow prisoners, it was here that the typical guard versus prisoner stereotype vanished and a close friendship ensued. Bulger later noted that once the day’s work was completed, Bloomie allowed the men to work out and talk amongst each other. Bulger admired him for being respectful and trusting of the convicts and never abusing his power over them. He commented on Bloomie, “The respect for Bloomie rose to such a level among the prisoner population that there was unspoken code among the men that in the event of any escape attempt, Bloomie would not be harmed. For me, he became a trusted friend even following my release from prison. It’s ironic, as the Hollywood depictions of the relationships between inmates and officers were often conflicted and full of strife, but Bloomie became an iconic figure to me. Looking back to my tenure at Alcatraz, I remember him with deep sense of admiration and reverence. Following my release, we met over several dinners and we enjoyed talking about our families and both looked towards the future with great optimism.
Another prominent figure to Bulger was Mickey Cohen, 1518-AZ. He arrived on Alcatraz in July of 1961 and Bulger later acknowledged that he admired Mickey and how he held himself in the company of fellow cons. Cohen often gave the young Jimmy Bulger a nod as they passed each other in the cellblock during meal periods and when he’d pick up his weekly clothing issue. He mostly keep to himself, but stood proud and was respectful to everyone no matter of race or criminal affiliation, including officers. Bulger later commenting, “Mickey was a proud little guy and a survivor. He was very well liked by all the guys at Alcatraz…

37 blog post; Mickey Cohen, 1518-AZ
Mickey Cohen, 1518-AZ

Bulger was also a close insider to the 1962 Alcatraz escape of Frank Morris and the Anglin brothers. Having struck a friendship with Morris in Atlanta, he helped offer advice on the best methods for not only the mechanics of the escape, but also how to avoid being captured during their years of freedom. It was during those discussions that he took those best practices and credited them for help in his own evasion of being captured for more than sixteen years. He has remained firm that he is a believer in their survival and that severing all ties with family and friends was essential. He noted, “In order to survive, I understood the importance of breaking all contact with loved ones and holding to that level of discipline. It was tough to break those ties with those you love, but necessary for my own survival and their protection. We all knew the penalty that would fall on the innocents we cared for. You have to factor that into as to why they were never seen or heard from again. Freedom came at such a big price, but it was still better than the long and lonely years spent in prison.
The famed escape was a profound event of his lifetime and he remembered the men of Alcatraz and the escape that many believed help close Alcatraz. He noted, “The morning of the escape was one of the happiest moments of my life. I can still remember it as if it were yesterday. When the frantic guards realized that Morris and the brothers had escaped, the cheers were so loud that it could be heard for miles! As far as I’m concerned, it was the greatest escape in the history of the U.S. and achieved under the most extreme security measures. The hope of the Warden was ‘They Drowned!’ Convicts believed ‘They Made It!’ I think they could have made it fairly easily. They likely stole a car and had many miles behind them before making a move to get money. They were smart and they had different phases and several contingencies in their plan. They put a lot of distance between them and Alcatraz in quick time. They also knew how to avoid suspicion. One guy fronts and the other two stay completely off scene. They stay completely isolated just watching TV and reading. Like President Lyndon Johnson once said about the smart Texas mule, ‘A big storm comes and the mule hunkers down and lies there still, quietly waiting for it to just blow over.’ The saying went something like that, but I thought of it often during my own time on the lam…
James Bulger was finally transferred off Alcatraz in July of 1962, only a month following the great escape from Alcatraz. He was finally released from prison in 1965 and federal prosecutors would later say that Bulger led south Boston’s Winter Hill gang from the late 1970s through the mid-1990s, one of the most powerful crime syndicates in the United States. In 1975, it was alleged that Bulger made a deal with the FBI where he provided information about the Italian Mafia in exchange for protection from prosecution. It was an allegation he firmly denied and brought forth collaborating testimony that he never provided any information of value to authorities. He it made crystal clear that he bought information but never sold it for any price.
In January of 1995, his FBI handler and friend from childhood tipped him off that an arrest warrant on racketeering charges was forthcoming and it was a matter of time before several mafia related murders would be attributed to him, resulting from plea deals made my other former associates. He would disappear for nearly sixteen years despite one of the most aggressive fugitive manhunts in history.

37 blog post; Bulger's apartment
The quiet apartment complex in Santa Monica, California, where Bulger was captured in 2011 after 16 years on the run. He resided in the apartment on the top floor, far right.

On June 22, 2011, the FBI arrested Bulger and his girlfriend, Catherine Greig, in a modest Santa Monica apartment building on the coast of southern California. At the time of his capture, he had risen to number one on the FBIs “Top Ten Most Wanted List.” Here, he had lived a quiet life and mostly led a crime free existence. Even in his later life, Bulger always looked back at his years on Alcatraz with nostalgia and fond memories of old friends. When looking through books chronicling the island’s history, he likened it to browsing through an old high school yearbook. The memories bittersweet. Tough years with solid friends. He held the men of Alcatraz in high regard and when he later learned of “Joe” Carnes death and burial in an unmarked paupers’ grave, out of sense of respect and their friendship, he had him exhumed and provided him an expensive casket and proper ceremony and burial. Bulger tried to peel away the myths about his life portrayed in Hollywood films.

37 blog post; Clarence "Joe" Carnes, 714-AZ
Clarence “Joe” Carnes, 714-AZ

Just before Bulger went on the lam, he visited Alcatraz with his then girlfriend Theresa Stanley. They visited his old cell block and reminisced about his years on the Rock. Even decades after his release from prison, there was one trademark several of his associates remembered…the Alcatraz belt buckle he always wore. It was a symbol of his past and the many friendships he held during some of the toughest years of his life. For many of the men who first stepped foot on Alcatraz, their criminal past had come to a close, but for James “Whitey” Bulger, it was only the beginning.