Re-Examining Whitey Bulger: A Look At His Early Criminal Life And Those Times: Part 3

If I Had The Wings
Of An Angel

How bad is Whitey?

When he’s arrested for the three bank robberies, the Boston Globe on March 5, 1956, noted Bulger first came to the attention of authorities in 1948 when he was arrested in Southie for an attempted criminal assault. What happened after that is pretty easy to understand if you knew how things operated back in those days. I happen to know this because my father was chief probation officer in Dorchester. Things like this couldn’t happen now because of all the formalities we’ve introduced into our system.

When a kid like Whitey was brought into the court either the clerk or chief probation officer would pull him aside and say, “look sonny, you got a choice, jail or the service.” They’d give the kid a few days to make up his mind. If the kid opted for the service they’d destroy his criminal record. My father told us on many occasions that these men came back and to thank him for what he did. They were able to get on jobs where a criminal record would have disqualified them.

Whitey went off to the Air Force where he served four years. For restless youth living on the cusp of a criminal life the service was a growing up time with its discipline, the structure teaching responsibility, and the chance to work and play with other Americans. That is the true melting pot where the ingredients have to blend and the sharp edges of prejudices are toned down. Most came out with a different attitude and went on to college and a law-abiding life. Then there were the Whiteys.

Again the Globe has an article on July 1, 1953 telling about the Boston cops looking for guys doing tailgate jobs. A couple of detectives watch a car following a beer truck. When the beer truck pulls up at the corner of Mass Ave and Boylston Street the driver gets out and enters the store. The car pulls up behind the truck. Its two occupants jump out and start opening its rear gate planning to hoist a few cases of beer and the cops grab them. In their car they find the loot from a truck that had cigarettes stolen from it the day before.

Whitey age 23 and Dick Kelly, 30, of Roxbury are arrested. Whitey’s hardly had time to change out of his uniform than he’s back committing crimes. He manages to avoid arrest until 1956 for the Hammond, Indiana and Pawtucket, Rhode Island bank robberies. Later he is charged with one he did in Melrose, MA.

The Globe reported on January 7, 1956, the FBI announced it was looking for him for the Indiana robbery. It noted he is sometimes called Sonny or Whitey. Of interest, “Two women acted as lookouts in the escape car, according to the FBI. They are about 20 years old.” 

I note that because the FBI had the option to charge those women with involvement in the robbery. When Whitey was arrested on March 4 the FBI agents suggested to him that if he quickly confessed to the robberies and told his girl to cooperate with the agents that they’d give her a pass. She did. She was never charged. Whitey took the hit and it came fast.

Whitey is arrested on March 4th. He’s held in $50,000 bail on the 5th.  A hearing was then scheduled for the 19th.  The next we hear is that on May 5, 1956, Billy O’Brien. 30, of Dorchester is arrested up in Vermont. He pulled the Melrose robbery along with Whitey.

No doubt none of these guys got their Miranda rights. Miranda didn’t come in until ten years later. I doubt they had lawyers. Back in those days for guys who confessed it was a quick shuffle off to the can.

Look at the time line. On June 21, three and a half months after he was arrested Whitey pleads guilty to the three robberies. He gets 20 years. Billy O’Brien a month and a half after being arrested is off for eight years to prison. Justice then was like it should be, sure and swift. Whitey’s 20 years gives lie to all those who suggest he was some type of informant.

Whitey did nine of his twenty years in prison. Not much to tell about there. He had a hard time adjusting being suddenly dropped among some of the worst people our nation has produced. He fought the system and lost every time in his early years. He finally settled in to doing his time. May have gotten some years knocked off for being an LSD guinea pig. But mostly did hard time, Alcatraz wasn’t known for its amenities.

For all the influence that the media would have us believe he was supposed to have among so many powerful people, it certainly didn’t help him out much during these years. He was just another con biding his time. When so many in America adulate these gangster’s lives they should open their eyes to the less than glamorous life of being locked-up. Prison is prison. It’s best avoided.

Whitey gets out of prison in 1965.  Thirty years later he’d flee when the feds indict him for racketeering.  (to be continued)


2 thoughts on “Re-Examining Whitey Bulger: A Look At His Early Criminal Life And Those Times: Part 3

  1. I think that in examining the earlier portion of Whitey’s criminal career, it is important to note that he did not begin his 20 year sentence at Alcatraz. In relation to his “fighting the system”, he was sent to Alcatraz as either a punishment or due to being a security risk. This is significant because not only does it suggest that Whitey was not a “cooperative” inmate, or an informant within corrections, but also because being housed in Alcatraz put him around the worst of the worst this country had to offer by way of criminal at the time. Many brains to pick…and aspects of leading a criminal life to learn. In regard to him serving less than 50% of his original sentence, that lends to the idea that he participated in the MK Ultra program. It doesn’t seem right that a violent criminal convicted of violent crimes would serve 9 of a 20 year sentence. And, as I suggested, he didn’t seem to be a model inmate deserving of a sentence reduction. If he was a guinea pig for LSD testing, this would have marked the 2nd time he participated in a specialized government program (for criminals), similar to accepting military service as a youth (as you suggested), and also similar to the program he would later participate in with the FBI.

    1. John:
      I agree with your analysis of why Whitey was sent to Alcatraz. He was a hard guy to handle. I hadn’t thought of it but you make a good point noting Whitey was not “an informant withing corrections.” Thanks for noting that. You also mentioned the MK Ultra program which I did not know was the name of the LSD program Whitey may have been involved with. It seems the years Whitey was in prison coincided with the time that program was at its height. Wikipedia talks about it. I see the files were all destroyed by the CIA in 1973 which made me think of how it destroyed the videos of its torture programs. That made me think that historians will never be able to accurately piece together the history of the CIA which seems to run contrary to the idea of what we should be doing in America. It’s also a telling statement you make that suggests Whitey’s mindset was to use the government to help himself. He needs to avoid jail so he joins the Air Force; he wants to reduce his time in prison so he volunteers for MK Ultra, and he wants to have cover for his criminal activities so he becomes a Top Echelon Informant. I suppose we could go one step further and suggest he’s now using the government in his later years for three hots and a cot and full medical coverage.

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