James "Whitey" Bulger

James “Whitey” Bulger: Legal Commentary

In this courtroom sketch, Steven Davis, second right, brother of slain Debra Davis, is comforted by his wife, right, as he testifies at the sentencing hearing for James "Whitey" Bulger, left, at federal court in Boston, Wednesday, Nov. 13, 2013. Photo /AP - Jane Flavell CollinsNovember 14, 2013: At 84 years old, James “Whitey” Bulger will spend his remaining days as a guest of the United States Bureau of Prisons. Sentenced to two lifetime prison sentences — plus an additional five years on top of that — for his lifetime of crime “unfathomable acts conducted in unfathomable ways,” as described by Judge Denise J. Casper.

Bulger was convicted in August of a laundry list of gangster crimes, including 11 murders and 31 other counts including extortion, drug trafficking, racketeering and money laundering.

In a blistering opinion from the bench, Casper told Bulger that the “scope, callousness and breadth of your crimes are almost unfathomable.”

Bulger was further ordered to pay nearly $20 million to the families of his victims and to forfeit an additional $52 million to the government. It’s unclear if he actually has that kind of money.

There’s nothing surprising about this sentence, given the severity of Bulger’s crimes and conviction. From the moment Bulger was arrested, everyone involved knew he would be spending the rest of his life in custody. He was simply too big, too involved in some of the worst criminal behavior Boston has ever seen, to prevail on any defense theory.

Bulger’s proffered theory, that he had immunity and a “license to kill” from the FBI because he was working with the Bureau as an informant, was never presented at his trial. The court refused to hear the defense, and Bulger denounced the trial as a sham and refused to testify. Instead, his defense lawyer attempted to discredit prosecution witnesses and make the case that corruption within the FBI lead to the gangland murders.

Bulger will almost certainly attempt to raise the immunity issues on appeal, but first he needs to get past potential homicide prosecutions in Florida and in Oklahoma, both states which use the death penalty, unlike Massachusetts.

Pre-Trial: Probably the biggest obstacle facing the prosecution is Whitey’s age and infirmity. When he was arrested, he seemed in ill health, and at age 82 in a uniquely stressful situation, it’s possible he might not outlive the case against him.

The prosecution should have no problem proving their case, however. They have supplied Whitey’s defense lawyers with documents and recordings so voluminous defense counsel told the court that it would take him over a year to review it all. Sworn statements from informants will also be crucial in proving that Whitey was responsible for these crimes, many of which are now 20 years old.

It’s clear from the stiff sentence handed down to Catherine Greig, Whitey’s girlfriend, that everyone involved in this case is playing for keeps. If Whitey were found guilty of even a single one of the charges pending against him, he would be looking at a life sentence at his age. Even so, it’s apparent that no one will be cutting him a break based on his age and health.

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Jofus says:

I fully expect that Bulger will change his plea to guilty, given that the stress of a trial that might last until Thanksgiving could literally kill him, given his age and poor health, and that such a change will come prior to the start of the trial (maybe in May).

Living five or six years in prison may be preferable to dropping dead this summer because of stress from the trial.


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