United States v. Bulger

Decision Date04 March 2016
Docket NumberNo. 13–2447.,13–2447.
Citation816 F.3d 137
Parties UNITED STATES, Appellee, v. James J. BULGER, a/k/a Jimmy, a/k/a Whitey, a/k/a Jim, Defendant, Appellant.
CourtU.S. Court of Appeals — First Circuit

Henry B. Brennan, with whom James H. Budreau was on brief, for appellant.

Randall E. Kromm, Assistant United States Attorney, with whom Carmen M. Ortiz, United States Attorney, was on brief, for appellee.

Before THOMPSON, KAYATTA, and BARRON, Circuit Judges.

THOMPSON, Circuit Judge.

After evading authorities for fifteen-plus years, fugitive James "Whitey" Bulger, the head of an organized crime syndicate in Boston from the 1970's to the 1990's, was captured. Bulger, who had been indicted in connection with a racketeering conspiracy while on the run, was brought to trial. The jury found him guilty of the vast majority of charged crimes and he was sentenced to life in prison. Bulger appeals the conviction, claiming that he was deprived of his right to a fair trial when both the government and trial court got a few things wrong prior to and during trial. Having closely considered the array of claimed errors, we affirm.

I. BACKGROUND

The factual underpinning of this case is considerable. The events span decades and the cast of characters is large but this appeal is circumscribed in scope making only certain details pertinent. We chart the relevant origin and travel of the case, saving the facts related to the maintained errors for later.1

A. The Indictment

In 2001, Bulger, who was on the run and had been for some time, was charged with thirty-two counts of a racketeering indictment along with Stephen Flemmi.2 It alleged that Bulger and Flemmi were members of a criminal organization known as Winter Hill (or some variation on this moniker) and part of a racketeering conspiracy that extended from around 1972 to 2000 in South Boston. Bulger, it said, participated in multiple racketeering acts, including nineteen murders, extortion, narcotics distribution, and money laundering.3 There were also an assortment of weapons charges, e.g., possession of firearms and machineguns in furtherance of a violent crime, possession of unregistered machineguns, and transfer and possession of machineguns.

B. Arrest and Trial

Law enforcement finally caught up with Bulger in June of 2011, finding him living under an assumed identity in California. He was arrested and from there brought back to Massachusetts to stand trial.

There was a good deal of pretrial skirmishing among the parties and rulings from the court, the particulars of which we will detail later. The same goes for the midtrial clashes and edicts. We will chronicle those later too. For now we focus on the substantive case that was presented to the jury over the course of the three-month trial.

C. The Government's Case

The government called scores of witnesses: participants in Bulger's operations, law enforcement officials, and forensics experts. Some of the testimony came from Bulger's closest Winter Hill associates—Flemmi, John Martorano, and Kevin Weeks—who had all cut plea deals with the government, swapping their cooperation for various benefits. The jury heard the following.

The government placed the start of the conspiracy at a 1972 meeting where Bulger's gang and another gang decided to go in together on some kind of "gambling business" that targeted individuals not affiliated with the mafia (also known as New England La Cosa Nostra). A string of murders followed in the ensuing years, which testimony linked Bulger to, along with other criminal activities.

Then around 1975, according to government witnesses, Bulger began acting as an informant to John Connolly, a Federal Bureau of Investigation ("FBI") agent. At some point, their relationship turned corrupt. Martorano and Flemmi (the latter, by his own admission, had been an FBI informant dating back to the 1960's), testified that Connolly began alerting Bulger to investigations being made into Winter Hill's illegal conduct and Bulger, in turn, lavished Connolly with gifts and cash, with approximately $230,000–plus going to Connolly over the years.4

For Bulger and his cohorts, the 1980's brought more murders and the continued use of violence to extort large sums of money from individuals. There were also a couple newer ventures: shaking down drug dealers for a share of their profits and purchasing real estate utilizing illegally obtained money.

The enterprise began to crumble in the summer of 1990 when law enforcement arrested some individuals involved in Winter Hill's drug venture. Fast forward a few years to 1994 when, according to cohort Weeks, he was approached by Connolly who informed him that indictments for Bulger and Flemmi "were imminent." Weeks passed on the message to both. Bulger took heed and fled, and after some short-term stops in New York and Chicago, ended up in Santa Monica, California, where he remained until his June 2011 arrest.

For his part, Flemmi stuck around and indeed was arrested in January of 1995. He tried to avoid being prosecuted, arguing during pretrial proceedings that he had been a secret FBI informant and so was immune from prosecution. With the courts holding otherwise, See United States v. Salemme, 91 F.Supp.2d 141 (D.Mass.1999) ; United States v. Flemmi, 225 F.3d 78 (1st Cir.2000), Flemmi agreed to cooperate with the government. In 2003, Flemmi pled guilty to twelve murders, extortion, narcotics crimes, money laundering, obstruction of justice, perjury, and firearms charges. By the time of Bulger's 2013 trial, Flemmi was serving a federal life sentence, as well as life sentences in Oklahoma and Florida. Because of his agreement to assist the government, Flemmi avoided the death penalty in those two states and got placed in a Federal Bureau of Prisons segregated unit for government witnesses (according to Flemmi, the living conditions are better there than in general population).

Like Flemmi, Martorano was arrested in January of 1995. Martorano, who had been a fugitive since 1979, was picked up down in Florida. He pled guilty to various federal charges, including ten federal murders, as well as two state murders. In exchange for cooperating against Bulger (if apprehended) and Flemmi, Martorano got just a fourteen-year sentence, to be served in a special facility for government witnesses, with five years' supervised release. On top of that, Martorano was allowed to use property seized by the government to settle a judgment his ex-wife had secured against him. He was released from prison in 2007.

Weeks was arrested in November of 1999 by the Drug Enforcement Administration and Massachusetts State Police. He pled guilty to racketeering crimes plus five murders, and received immunity for some state crimes, in exchange for his full cooperation. The plea terms required him to testify in any case that was pending or brought within three years of his plea agreement. Bulger's trial marked the fifth or sixth trial that Weeks took the stand for.

As for Connolly, Bulger's FBI handler, he was indicted in 1995 (along with Bulger, Flemmi, and Martorano) for the murder of a businessman that Winter Hill had dealings with. Connolly was convicted by a jury some years later. At the time of Bulger's trial, Connolly was serving his sentence down in Florida, after having also been convicted of some federal charges in Massachusetts stemming from his relationship with Winter Hill.

D. The Defense

Bulger's defense strategy was laid out during opening statements. It was not a wholesale denial of any criminal wrongdoing. Instead counsel tried to poke holes in the government's case by casting doubt on the veracity of the cooperating witnesses' testimony, namely Flemmi, Martorano and Weeks. The defense harped on their background and character, as well as "the unbelievable incentives the prosecution has given these three men so that they will testify in the manner that the government wants." It also sought to undercut the prosecution's case by emphasizing the rampant corruption among federal law enforcement at the time. And counsel vigorously disputed the notion that Bulger had been an informant, instead claiming that he paid Connolly and other law enforcement members large sums of money in exchange for information meant to ensure the continued productivity of his criminal enterprise.

These themes continued through the defense's cross-examination of government witnesses and direct examination of its own witnesses, namely law enforcement agents. Bulger did not take the stand.

E. The Verdict and Sentence

Eventually both sides wrapped up and after deliberating for four days, the jury found Bulger guilty on all counts, save one extortion count. With respect to the racketeering count in particular, the jury found the government had proven some, though not all, of the thirty-three racketeering acts alleged. The proven ones included the murder of (and sometimes also the conspiracy to murder) eleven individuals, multiple instances of extortion and money laundering, and one act of narcotics distribution conspiracy. Following a hearing, the trial judge sentenced Bulger to life in prison, with an additional life and five-year sentence to be served consecutively.

F. This Appeal

Bulger timely appealed. As alluded to above, he assigns error to various court rulings and condemns certain actions of the government. Bulger would have us find that standing alone, or cumulatively, the alleged miscues warrant reversal of his conviction and a new trial.

II. IMMUNITY

Bulger's first claimed error relates to the court's pretrial decision that barred Bulger from asserting at trial that he was immune from prosecution, immunity, Bulger says, he was granted long ago by a government attorney, one Jeremiah O'Sullivan. We start with what happened below.

A. Background

Prior to trial, the defense filed a discovery motion seeking all correspondence between various law enforcement agencies, e.g., FBI, United States Attorney's Office, Department of Justice ("DOJ"), and individual Winter Hill...

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