‘How To Become A Mob Boss’ Episode 5 Recap & Ending: What Happens To James “Whitey” Bulger?

The fifth episode of How to Become a Mob Boss revolves around the life of Boston’s most powerful mob boss, James “Whitey” Bulger. He had managed to keep his proceedings undercover for a very long time, making him one of the most nearly invincible individuals on the face of the earth. He had done everything right to extend his shelf life as a mob boss and had taken all possible precautions to keep himself from getting caught. His predicting capability helped him obliterate every threat coming his way! How heinous were his crimes? Did he finally get caught? Let us find out!


Spoilers Ahead

What Was Whitey’s Reputation in Boston?

James “Whitey” Bulger was the head of Boston’s Winter Hill Gang and was well known for having ordered at least 19 murders and ranking an estimated $30 million in illicit cash. Emily Sweeney, the reporter for the Boston Globe, said he was one of the most successful criminals located in Boston at that time. Dick Lehr, the author of “Black Mass and Whitey”, was of the opinion that he had outwitted everyone along the way. During the 1940s, he grew up in poverty in South Boston and was the oldest of three boys. He was neither into school nor church and got into crimes and got away with them from an early age. During the 1950s, he had risen to the peak of infamy, and in one of the arrests, he was found guilty and tried for a bank robbery. His associates had ratted him out, but later, he moved up the ladders to become an important part of New England’s Syndicate. With a hold on the Syndicate came a lot of wealth and power!


What Did He Do To Keep Himself Out Of The Radar?

Publicity was one of the greatest enemies of Whitey. He kept close track of all the activities and had total control of the operations. He had zero tolerance for any weak links in the gang. Michel Franzese, a member of the Colombo family, is of the opinion that tight control over the members of the gang was important during those times, and Whitey had very few people in his inner circle. He had two main allies, Steve Flemmi and Johnny Martorano, whom he trusted blindly. Whitey also had other strict rules, such as no flamboyant display of wealth, no unnecessary messing with law enforcement, not talking about business, or ratting anyone out. One of his gang members, Tommy King, the enforcer of the Winter Hill Gang, was seen as a threat by Whitey as a result of his erratic behavior. He had Tommy killed and later spun the story that Tommy had committed a murder and skipped town. The moment he thought someone was a liability to him, he got them removed from the system, but murdering people had its own side effects.

He was quite invested in covering up murder trails! Bobby Luisi, the former underboss of the Patriarca family, stated that covering up the DNA was the best way to cover up a murder. Pablo Escobar got rid of some members of his gang who were cheating him after he invited them to his private prison and got them incinerated. Paul Castellano had hired Roy DeMeo, a hitman, to eliminate his rivals by chopping them up and making them disappear. Salvatore Riina used the method of “lupara bianca” to dissolve victims in acid. Whitey also used methods to hide bodies where nobody could find them by cutting out fingers and pulling out teeth to remove any identifying feature of the bodies.


He made use of a deserted house in Boston to kill and bury his victims, which earned the house the nickname “haunt.” After the house was put up for sale, he used one of his associates to move the bodies and drive them across town, beside the fireman’s Union Hall, and bury them there. He was a dangerous murderer. Many of his murders were left unsolved for several years. He paid off the cops and tried to keep them out of his way! Just in case he was caught, he had kept his plans ready. The steps included starting to save early by stashing cash and jewelry. The second step involved building aliases by paying huge sums for creating fake IDs, passports, or credit cards with different names. The third step included finding the perfect hiding place, which had a lot of tourist influx, so that he could easily blend in. Finally, he also maintained secrecy about when, where, or how he was leaving.

How Did John Connolly Help Whitey?

He had an old friend, John Connolly, an FBI agent in the Boston Field Office. He had grown up in Boston and idolized Whitey because he had once protected Connolly in a street fight. In 1974, Whitey discreetly met Connolly to garner VIP treatment from the local FBI. He tipped off Connolly about other mafias in Boston. The head of Boston’s Italian Mafia, Jerry Angiulo, was nabbed by the FBI after they gained information from Whitey. Conolly kept Whitey’s name out of the records of the FBI, making him invincible! However, not a single soul in the underworld knew about him ratting their names out to the police because he was leading a discreet double life.


Had the underworld known about his big mouth, he would have ended up like some of the other rats! Big Jack Zelig, the boss of Manhattan’s Eastman gang, got killed in 1912 after the underworld learned that he was working with an NYPD official. Chicago crime boss James Ragen got ambushed and shot after exposing Chicago mobs to the police. However, another threat comes Whitey’s way when, in 1981, Debra Davis, Steve Flemmi’s mistress, gets to know about Whitey’s association with the FBI. Flemmi and Whitey planned on killing Debra and eventually proceeded with their plan.

How Did Whitey Escape?

By 1992, Connolly had already kept Whitey safe for 20 years. However, in the early 1990s, his luck started fading after his ally Flemmi got arrested. Connolly had helped Whitey escape the law, and he went and settled in Santa Monica with his long-time girlfriend, Catherine Greig. They had given up their original names and taken up new names to hide their real identities. They stayed away from their neighbors, but Whitey befriended homeless people to steal their IDs. He told all of them that he was an illegal immigrant from Canada and needed medical assistance. He paid most of the people a hefty sum of money for their social security numbers and driver’s licenses. He stayed undercover for the next 16 years, which was one of the longest for a wanted criminal like him!


How Was Whitey Caught?

He was finally caught because of a cat! A woman from Iceland had come to spend her winters in Santa Monica and bonded well with Catherine over her cat. Just when he saw Catherine on television, she recognized her and reported her to the FBI. Within 24 hours, they were near Whitey’s residence, and he got arrested. They found many arms, ammunition, and fake IDs at his residence. The crafty ideas of Whitey helped him remain a fugitive and enjoy his time out of prison for a very long time.

Final Thoughts

Whitey is a perfect example of a very crafty mobster. Despite being in a very risky business, he followed certain tricks and tactics to keep himself alive and in the business. Staying out of the radar of the police for 16 long years was not very easy! The life story of Whitey is portrayed very effectively in the 30-minute-long fifth episode of How to Become a Mob Boss.


Notify of

Inline Feedbacks
View all comments
Debjyoti Dey
Debjyoti Dey
Debjyoti’s obsession with creativity and travel fervor has helped her branch out into the entertainment genre. Her love for psychological thrillers helps her get a daily dose of adrenaline. A regular caricature of the films and its characters is what keeps her going!

Latest articles