The Angiulo mob was indicted on September 19, 1983, in a massive racketeering case built largely on the electronic bug the FBI had installed at the Prince Street headquarters. Eventually, the conviction of all major members of the group resulted in its dismantling. For a time, Boston was free of a ruling Mafia crime family while other criminal groups vied for the newly vacated top spot. The prosecution was considered one of the most successful in the annals of Department of Justice assaults on organized crime.
But taking down the Boston Mafia was not enough for the DOJ. In December 1984, the feds indicted Cintolo for obstruction of justice growing out of his representation of the Angiulos and LaFreniere. The DOJ claimed that even though he had technically been disqualified from representing Jason Angiulo before the grand jury, Cintolo continued representing the interests of the Angiulo family during the grand jury investigation. The prosecutors alleged that Cintolo had used his position as attorney for LaFreniere not to further LaFreniere’s interests, but to gather information for his “true” client, the Angiulo mob, and to make sure that LaFreniere continued refusing to testify against the family.16
The surreptitious Prince Street recordings were played for the jury at Cintolo’s trial. The tapes showed that the Angiulos were concerned that LaFreniere would weaken and testify once immunized, and that they consequently suggested to LaFreniere that he hire Cintolo; the Angiulos also suggested to Cintolo that he accept LaFreniere’s request for representation. At a later meeting, the bugging tapes demonstrated, Cintolo shared with the Angiulos the questions that LaFreniere had been asked at the grand jury, questions that the client had duly reported to Cintolo, along with the fact that LaFreniere had refused to answer. (Earlier, the Angiulos had been told by Venios what questions were asked of him at the grand jury, and Gennaro duly reported that to Cintolo.)
There was some controversy at the trial about whether the lawyer actually knew or had reason to know that one of his clients, Gennaro Angiulo, had in mind to murder his other client—Walter LaFreniere. The plot to murder LaFreniere was caught on tape; Cintolo was not in the room when it was hatched. However, Cintolo was aware of the Angiulos’s concern about whether LaFreniere could stand up to pressure and accept a contempt sentence rather than cave in and testify. Cintolo also had learned, well before he was indicted and while the bug was still recording the goings-on at Prince Street, from a federal prosecutor and from LaFreniere, that “an informant” had told the FBI that the Angiulos were determined to assassinate LaFreniere. Cintolo testified that he did not believe there was a “hit” contract on his client, but rather that it was concocted by the FBI to scare LaFreniere into becoming a cooperating (and protected) federal witness. But, of course, Cintolo could not be certain. (Such phony FBI scare tactics are hardly unknown, as any experienced criminal defense lawyer can recount.)
At the time that the “hit” contract was issued, Gennaro Angiulo had gotten information that LaFreniere, when the feds tipped him off to the murder plot, was trying to reach Cintolo. Angiulo promptly told Cintolo that the reason LaFreniere was trying to reach the lawyer was because the feds had just warned his client that a contract had been put out on his life. Remember, Angiulo never did tell Cintolo whether there was or was not a plot to murder his client, much less that Angiulo had ordered the hit. The prosecutors took the position that Cintolo had heard enough to put two and two together and recognized that one group of his clients was out to murder (and thus silence) the other client. It remained a contested point whether Cintolo knew that Angiulo was sufficiently nervous about whether LaFreniere was a stand-up guy to launch a plot to murder him.
The heart of Cintolo’s obstruction prosecution was not that he played any role or had any knowledge of the plot to assassinate one of his clients to protect the others. Rather, the indictment charged that by representing both the targets of the grand jury and a witness whose testimony was sought, unsuccessfully, against the targets, and by encouraging LaFreniere to keep silent even in the face of a contempt-ofcourt prison sentence, Cintolo had abused his role as a lawyer and had thereby obstructed—indeed, polluted—the processes of justice.
The prosecutors sought to bolster their case by arguing that the tactics Cintolo employed while representing LaFreniere were frivolous legal maneuvers destined to (and in fact they did) lose in court. At bottom, the government’s position was that there was nothing that Cintolo could, or should, have done for LaFreniere except assist him while he testified. While a witness, the government conceded, has every right to refuse to testify on the basis of the constitutional privilege against self-incrimination, a lawyer who advises a client to invoke the privilege, and who continues to represent the client who remains recalcitrant even in the face of an immunity order, is, in the government’s eyes, guilty of obstruction of justice if his true allegiance is to another client, namely the target of the investigation or prosecution. And so the Cintolo prosecution proceeded on a theory that while each of the tactical moves engaged in by Cintolo on behalf of LaFreniere was lawful in itself, the whole of the representation, being a sham based on Cintolo’s true allegiance toward the Angiulos, constituted the crime of obstruction of justice.
The judge at Cintolo’s obstruction of justice trial didn’t buy the theory in its entirety and told the jurors that the evidence did not demonstrate Cintolo’s actual knowledge of a plot to kill LaFreniere. The jury nonetheless handed the Mafia-hunting DOJ another victory. Cintolo was convicted, sentenced to two years in prison, and automatically disbarred.
Members of the criminal defense bar recognized immediately the threat posed by such a prosecution and its underlying theory. It greatly hinders the ability of any perfectly honest and ethical criminal lawyer to render zealous representation to a client or clients. All lawyers are taught in law school that, as a matter of professional ethics within an adversarial system of justice, a lawyer must not merely represent a client, but must do so with “utmost zeal.” The defense lawyer is tasked with doing anything and everything within the law to protect the client from prosecution or penalty. In Cintolo’s case it was precisely his observance of that ethical requirement that the DOJ sought to punish. A special challenge is presented to both lawyer and client when the very path taken by the lawyer to protect the client is seen not as the fulfillment of the lawyer’s constitutional role and duty, but rather as a criminal venture by a rogue shyster or Mafia foot soldier with some goal in mind other than proper and lawful vigorous representation.
Responding to the government’s attempt to turn Cintolo’s representation of LaFreniere into a crime, the criminal defense bar made its views known. When Cintolo’s case went up to the U.S. Court of Appeals for the First Circuit, two groups filed an amicus curiae (“friend of the court”) brief on his behalf. In their joint amicus brief, the Massachusetts Association of Criminal Defense Lawyers (which I co-founded and which I co-chaired at the time, with my then-partner Andrew Good) and the National Network for the Right to Counsel, chaired by Boston attorney Max D. Stern, registered a stark warning: to allow the conviction of Cintolo on the facts presented would send a chill down the spine of every ethical and effective criminal lawyer in the country and, in the process, deprive defendants of their constitutionally mandated right to counsel.
“Never before, to the knowledge of amici, has a jury been permitted to determine whether an attorney should be held criminally liable for actions taken by the attorney in the course of advising and representing his client, on the ground that the motive for the maneuvers was delay rather than a bona fide belief in their eventual success on the merits,” the defense lawyers’ brief warned. Equally startling was the notion that a jury would be allowed “to determine that a lawyer’s advice to and representation of multiple clients was ‘corrupt,’ and hence unlawful, for the reason that the advice given to one client provided benefits to another client as well.” The brief pointed out that every action taken by Cintolo on behalf of either or both clients was in itself lawful, but that somehow his course of c
onduct was being viewed as criminal because the subjective “motive” was in some way “corrupt.” To allow this to happen, warned the defense lawyers, “changed the requirement that the lawyer act ‘within the bounds of the law’ from an objective limitation on what the lawyer may do in defense of the client, to an undefined proscription against any conduct which a prosecutor can convince a judge or jury was undertaken with a ‘corrupt’ motive.”
The criminal defense bar’s amicus brief did not seek to defend truly illegal, corrupt conduct by a lawyer. It did not adopt an “anything goes” approach, which would have been a legally frivolous and tactically disastrous argument. Rather, it cited such authorities as the American Bar Association for the proposition that it’s the lawyer’s job to advise the client on his or her alternatives, but the client makes the decision.17 And in the case of LaFreniere, he was entitled to make the decision to refuse to testify, even after being granted immunity, and to suffer the legal consequences of a contempt sentence. The defense lawyers further cited a 1985 federal court decision warning that once a lawyer has undertaken to represent a defendant and has explained all conflicts of interest to him, he may not withdraw from the representation except under compelling circumstances.18
The defense lawyers’ group urged the Court of Appeals to disallow prosecutions of lawyers under this general, amorphous obstruction of justice statute. Instead, the court should rely on “the more specific clauses and statutes which the government has available to punish illegal conduct of this sort.” For example, a lawyer may clearly be prosecuted if he “knowingly filed false statements with the government, or threatens a witness to alter his testimony, or bribes a judge or juror.” Such conduct, noted the amicus brief, is a crime no matter who commits it.
The defense lawyers then made an argument that should have made clear why the lawyer’s conduct could not be viewed as criminal without destroying his ability to represent his clients. “Because the defendant’s conduct was not itself criminal,” the brief argued, “the government had to prove that defendant had, at least, encouraged, endorsed or stimulated the illegal conspiracy in order to prove his intent to join it.” Yet Cintolo, whose voice had been secretly recorded by the FBI, had remained silent every time the Angiulos brought up their criminal schemes. “Not a single statement or action by [Cintolo] indicates that he was encouraging the Angiulos to undertake their criminal plans to obstruct justice.”
This latter point becomes particularly important when discussing the contract against LaFreniere. It may or may not be that Cintolo suspected such a contract was out on his client’s life, and even that his other client, the Angiulo family, was responsible for this threat. If so, any experienced criminal defense lawyer, who is privy to many dark secrets when representing real criminals, recognizes that a certain amount of discretion is essential in seeing that no further harm be done. In the case of LaFreniere, Cintolo did precisely what any ethical and effective lawyer should have done to protect the life of a client who had already decided that he would not testify against the mob: Cintolo told the head of the mob that LaFreniere had decided not to testify and instead to serve his sentence for contempt. Cintolo thereby very likely saved the life of his client LaFreniere, whether or not he knew or suspected it.19
The brief filed by the Department of Justice, signed primarily by then-United States Attorney (and later FBI Director) Robert S. Mueller III, took a more simplistic, Manichean view. Because Cintolo’s representation of LaFreniere was seen as benefiting Cintolo’s other client, the Angiulo family, his representation of LaFreniere was, said the brief, “a sham.” The DOJ brief twisted the murder plot on LaFreniere’s life, arguing that because Cintolo undertook the representation of LaFreniere after he had reason to suspect that his other client, the Angiulo family, planned to murder LaFreniere, the lawyer in effect joined in the conspiracy to murder his other client. (As stated above, it was more likely, particularly as events unfolded, that Cintolo saved LaFreniere’s life by helping LaFreniere put into effect the decision he’d made, before Cintolo became his lawyer, to refuse to testify against the Angiulos.)
It was clear that the prosecutors were somewhat disturbed by the arguments made by the criminal defense bar amici, since the prosecution’s brief repeatedly made direct reference to those arguments and sought to refute them. Normally, friend-of-the-court briefs play a decidedly backseat role compared to the party himself. But in this case it was clear that the battle was between the Justice Department and the criminal defense bar, not just one criminal defense practitioner who happened to be representing a very unappealing group of clients.
If the prosecutors were disturbed that the defense bar came to the aid of Cintolo, the Court of Appeals seemed doubly challenged when it concluded the proceedings by affirming Cintolo’s conviction. Much of the three-judge panel’s opinion responding to Cintolo’s claims actually addressed those raised by the amici. The court began with a reference to what it termed “the fabric of federal law which Congress has woven to prevent obstruction of justice.”20 But the opinion hardly laid out the strands of this supposed “fabric.” It instead repeated the government’s mantra: Cintolo’s “corrupt” intention transformed traditional criminal defense work into the sinister practice of obstruction of justice. Despite the fact that there was no evidence that LaFreniere ever entertained the notion of testifying against the Angiulo family, the appellate court referred to Cintolo’s “efforts to inhibit LaFreniere, after the latter had been granted immunity, from testifying truthfully before the grand jury, or from cooperating in any way with the investigation.”
An assumption (an entirely improper one that misconceives the role of the criminal defense lawyer in the adversary system) pervades the court’s opinion: it was somehow Cintolo’s job to encourage his client to cooperate with the FBI, even if such cooperation was against the client’s own view of his best interests and security. In fact, it was Cintolo’s obligation to protect his client from both the FBI and the mob as best he could. Both sides, after all, were trying to use LaFreniere for their own ends. For the system to work, criminal defense lawyers must look out for their clients’ (not their own, and certainly not government prosecutors’) best interests. The Court of Appeals therefore embarked on the dangerous path of equating a lawyer’s assisting the FBI with the lawyer’s duty and role in the adversarial system. This was a revolutionary idea that would seriously undermine the role of the independent bar in providing legal representation when a citizen is charged by the federal government with a crime. This revolution was effectuated by an appellate court too readily buying the DOJ’s “obstruction” theory based upon an utterly vague statute that would not readily be so interpreted by most lawyers, nor by anyone concerned about maintaining an independent bar within civil society.
The Court of Appeals was particularly hard on Cintolo about the murder contract on LaFreniere’s life. The FBI bug had picked up the conversation in which Gennaro Angiulo informed Cintolo that the FBI agents told LaFreniere that an “informant” reported the contract to the Bureau. The Court of Appeals contorted this part of the eavesdrop recording to make it sound as if Cintolo were utterly unconcerned about LaFreniere’s well-being. “Cintolo’s only response to this grisly piece of news,” wrote the court, “was to mention calmly that he had instructed LaFreniere to talk with no one, and to refer all calls to him.” Of course, Cintolo had no other option if, realistically, his goal was to protect LaFreniere’s life. Were he to assume a holierthan-thou posture and advise or warn Angiulo to leave LaFreniere alone, he would have destroyed any trust that Angiulo had built up toward the lawyer. Indeed, he would have cut off whatever avenue remained available to get information from Angiulo that would have affected LaFreniere. Cintolo would have destroyed his ability to allay Angiulo’s potentially murderous concerns. Instead, Cintolo did what was obviously in the best interests of his client LaFreniere. He sought to assure Angiulo that he had the confidence of LaFreniere and that LaFreniere had not changed his stance, consis
tent from before Cintolo began to represent him, that he would not testify. Without receiving such assurances, Angiulo might well have proceeded with the contract on LaFreniere’s life.21
The most telling portion of the First Circuit’s opinion was its view that, even if it were true that Cintolo acted to further LaFreniere’s interests, it would not have been enough. The court, like the DOJ, saw Cintolo as obligated to convince LaFreniere to cooperate with the feds, even at the risk of the client’s own life, and even if contrary to the consistent urging of his own father-in-law. (Recall that LaFreniere’s father-in-law, too, risked contempt rather than testify.) “In any realistic light,” the court wrote, “the most authentic victim of Cintolo’s behavior was not his nominal client, but the due administration of justice.” The Constitution, they argued, did not require them “to insulate lawyers from encroachments on the ‘zealous representation’ of clients accused of crime.”22
The court concluded that the general obstruction of justice statute required that Cintolo’s conduct be deemed a crime. This is precisely what the amici most feared: an equation between the traditional work of the criminal defense lawyer and the crime of obstruction of what the court saw as the interests of justice. All of a sudden, it was as if the defense lawyer was supposed to be working for the FBI rather than for his client.
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