§16: Re-Examining Whitey Bulger: The Learning Years: Surviving Among Sharks

The Unknown On
The Other Side

Whitey walked into a group of murderous guys who already had strong loyalties to others within the group. Could he hope for no more than being an outsider through the Learning Years? He and the Italians would never really be close friends. Italian and Irish gangsters are like oil and water. Their inherent love of their own and distrust of the other made their alliance one of convenience not friendship. If you ever attended an old Southie-Eastie game on Thanksgiving Day you’d have no doubt about it. Someday I’ll tell about one thing I would never forget.

When the chips were really down and the stakes were very high instinctively each one would stick to his own kind. That’s why all of them, Murderman, Salemme and Flemmi, in the end turned against Whitey dumping some of their own criminal acts on top of him, or at least including him as a partner in their most sordid crimes to get deals for themselves. That’s why they quickly propel Whitey to a leadership position so that they can include him in their criminal acts.

The members of the Roxbury group were well schooled in treachery. Murderman wrote that back in 1960 Stevie Flemmi was ratting him out to FBI Agent Paul Rico blaming Murderman for the things Flemmi was doing. Sound familiar with Flemmi?

Whitey wasn’t above a little treachery himself. Flemmi complained he cut him out of a cut of the lottery winning ticket; Murderman complained that he cheated him out of hundreds of thousands of dollars; and Salemme figured Whitey had something to do with him being gunned down at the Saugus IHOP.

Whitey had probably figured all of this out. He needed the gang for cover and protection for a small period of time until he could feel safe leaving L Street and driving past where the aquarium once stood and over to Castle Island. Whitey always understood on what side his bread was buttered. That was the Southie side. For all his vaunted reputation, Whitey really only wanted to be king of crime in the South Boston peninsula.

He only went to the Somerville gang through necessity. He accepted it as a tactical alliance for him which he planned to keep and needed until he became more firmly in control of his home turf. He probably didn’t envision at this time the golden opportunity he would be able to seize.

Whitey had going for him his wisdom developed from his readings and the knowledge he built up after his years of dealing with guys like his new partners when he was in the worst of prisons. He was intrepid, undaunted and extremely dangerous.

Murderman might call him a ham-and-egger, others of the tough guys might make fun of him outside his presence, but one universal truth is that no one did it to his face.  He epitomized the type of prince who Machievelli said would always survive. The one who was feared.

He was also never called Whitey to his face, only Jimmy. The patois of the tough Southie guys, who never knew when he’d suddenly show up, had it that the appropriate way to discuss him was to refer to him as Mr. White.

Despite all his deadly qualities, he’d need time to ingratiate himself with the others in Winter Hill. Like the general he thought himself to be, he had to study the landscape. He had to plan out his short-term moves and long-term goals. It would take time, maybe a long time with the Winter Hill gang. Meanwhile he could solidify his home front, Southie.


2 thoughts on Ҥ16: Re-Examining Whitey Bulger: The Learning Years: Surviving Among Sharks

  1. dear author, another interesting post. i would be very interested to know your thought process on how whitey was able to turn illegal money into legal money over many years and decades. by that i mean people take it for granted that whitey owned triple os , south boston liquor mart etc with kevin oneil being the name owner. do you know who did whiteys taxes all those years? can whiteys tax records be released to the general public? the irs got al capone ,what was the irs waiting for as the 1980s rolled on and whitey made millions from cocaine? i have read that whitey held mortgages ect besides his infamous rolls of 100 dollar bills. do you know how the money was cut up? i mean what did steve flemmi make? kevin weeks? kevin oneil? the old phrase follow the money seems timeless , i will always wonder why this not pushed harder by those in the know. regards,

    1. Norwood Born:
      I know nothing about Whitey’s taxes but I assume he filed as having some income and paid some taxes over the years. He was not going to fall into the trap of Al Capone and get into tax trouble. The reason he bought into the lottery winnings was so that he could show more income which would justify an uptick in his life style. Whitey took his illegal money and never made a show of it. He carried it about the country and overseas stuffing it into safe deposit boxes. His dilemma now is to retrieve some of it so it doesn’t escheat to the state. Weeks testified that the all put a part of their money in a common fund called the X Fund. Weeks testified Whitey and Stevie split it and would throw him a bit of each hit. They also kept Martorano supplied in Florida and spread some around but are mainly greedy individuals who kept most of it for themselves. The IRS isn’t that good at showing non recorded income. It usually needs a paper trail to bring about a prosecution. Whitey was disciplined and smart and told few what he did with the money. He lived a very modest life style. There was little the tax authorities could find to go after him.

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