Whitey Bulger & the FBI: Between a Rock and a Hard Place

James "Whitey" Bulger has been apprehended in California after more than 16 years on the lam. He is scheduled to be returned to Boston today. If Bulger arrives as scheduled he will make an initial appearance in United States v. DeLuca, et al, No. 94-cr-10287-MLW-3, before Magistrate Judge Leo Sorokin. Bulger will then make an initial appearance in United States v. Weeks, et al, No. 99-cr-10371-RGS-3, before Magistrate Judge Marianne Bowler. As these cases continue to develop, I see him having only two realistic choices. He can keep his mouth closed tight, plead guilty to all the charges against him to prevent the public release of all the sordid and gruesome details that will inevitably emerge during a lengthy trial on the allegations in both and, and take the “hit” of the almost certain life sentence that will follow, thus regaining a modicum of respect and dignity in the eyes of those who have relentlessly labeled him a “Rat”. Or, he can submit to full and exhaustive debriefings by the FBI and other agencies, admit to everything, fill in gaps on “cold cases” and help close-out open investigations, cooperate fully, completely and honestly with law enforcement, and also plead guilty to all charges and all counts. Ironically the result under either option is likely to be the same: serving the rest of his natural life behind bars. However, under Option A, he faces years of administrative segregation and lock-down (There are a lot of inmates who’d like a “piece” of him.), isolation and deprivation, and if reports of his poor health are true, probably the prospect of dying alone in a prison hospital a la John Gotti, as well. Under Option B, he’s still likely to serve the rest of his natural life in prison (Keep in mind under either Option he has basically zero chance at being released on bail and/or conditions.), but the reality is he’ll become the most “popular” inmate in the federal system for the time being with the daily monotony of his detention broken-up by non-stop law enforcement visits and debriefings, field trips with investigators, possible off-site interviews in the custody of U.S. Marshals and the FBI, and special “favors” like carry-in snacks and menu-of-choice lunches, as well as all in all “celebrity” treatment because, let’s face it, the happier the Feds can make him under Option B, the more likely he is to keep talking. To be sure, he can always decide to “fight” the charges and force the government to prove their case at trial, but given the wealth of evidence, and the number of witnesses/cooperators offering testimony, against him, and in view of already established precedents such as United States v. Salemmi, 91 F.Supp.2d. 141 (D.Mass 1999), United States v. Stephen Flemmi, 195 F.Supp.2d. 243 (D.Mass. 2001), and United States v. John J. Connolly, Jr., 341 F.3d 16 (2003), among others, the result seems all but foregone. So why not get it over with and avoid sitting through weeks and weeks of testimony and pubic revelations including those regarding his status as an alleged Upper Echelon/Rogue Informant? Yes, there’s still the issue of murder charges in Florida and Oklahoma, both of which carry a possible death sentence (avoiding which may well be the one true concession he may gain by cooperating), but at 81 and in ill-health, the likelihood is he is going to die in prison anyway. So, as the saying goes, he can do it the HARD WAY by pleading guilty, clamming up, “standing-up” and probably living out the rest of his days in isolation, or do it the hard way by “playing ball” with the Feds and remaining the center of their attention for at least the next several years. It’s the classic Hobbesian choice of being between a Rock and Hard Place but in this case, in his shoes, I might be tempted to eschew “the rock” and opt for the ‘hard place” in view of the Fed’s ability to at least supply me with a pillow.