Hard Cases Make Bad Law: The Tortured History of the Bill Cosby Prosecution

By David Louis Cohen and Robert J. Masters

Hard Cases Make Bad Law: The Tortured History of the Bill Cosby Prosecution

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On June 30, 2021, the Pennsylvania Supreme Court reversed the conviction and sentence of “America’s Dad,” Bill Cosby, and barred retrial on the charges of sexual assault. The ruling ignited widespread comment and raised questions about the legal steps leading up to the reversal. There is no question, however, that the Cosby case is an example that “hard cases make bad law,” as “The Great Dissenter,” Justice Oliver Wendell Holmes, is said to have once observed. To which we might add that if hard cases make bad law, then “celebrity cases make worse law.” Experience shows that whether O.J. Simpson, Michael Jackson, Mike Tyson or any number of well-known defendants – Roger Clemens, Barry Bonds, Marv Albert – are the subject of our process, the familiar, the ordinary and the routine are abandoned. And once forsaken, these norms are replaced by the unusual, unprecedented and untested, if not the entirely unique. Once what we know is swapped out for the newly invented, what follows is anything but predictable. Instead, the gross departure from the ordinary results in decisions made by all parties – the prosecution, the defense and the court – being based, not on precedent, but rather on an accommodation reached in the moment, designed to achieve immediate relief from an anxious media, or solve today’s legal predicament, without concern for tomorrow’s appellate review. Fortunately, for as hard as these celebrity cases always prove, because of their individual uniqueness, if not freakish fact patterns combined with the ramshackle remedies that are jerry-rigged to satisfy a momentary crisis, they rarely provide precedent for our daily practice. Rather, they live on as cautionary tales for practitioners, reminding us not to surrender to the temptations so often presented by such notorious cases.

This article will examine the legal steps leading up to the Supreme Court decision, from the perspective of both an appellant case and one that involved a once-beloved celebrity. But first we must make two disclaimers: one, we have little familiarity with Pennsylvania’s common law or some of the statutory schemes that are peculiar to the commonwealth. Nor do we criticize any of the parties, who were faced with many difficult choices resulting from such serious charges being leveled against one of America’s most successful and respected entertainers who, over a half-century, managed to achieve the status of cultural icon. It is our goal merely to demonstrate where these hard choices set the stage for the case’s unsatisfying conclusion – one in which the victim can feel neither contentment nor vindication – where Cosby has found liberty in his compromised health and advanced age, but without cleansing the disgrace that shadows him, and the attorneys will be consigned to explain their professional decisions, never made before or repeated since, that appear to be perfectly justified then, but through the prism of hindsight today, were destined to yield a conclusion of controversy.

The three separate opinions – the majority, a partial concurrence and dissent and a dissenting opinion – span 94 pages in length. Surprisingly, there is very little disagreement about what happened in the case and how all the parties came to this present posture. The disagreement from the court turned on the questions of just how unfair the unprecedented procedure of the case was to Cosby, whether it required reversal, and if retrial could remedy it or if equity could only abide terminating the prosecution.

The factual history of the case is thoroughly outlined in the court’s majority opinion. The alleged crimes occurred in January 2004 in Montgomery County, Pennsylvania, where Cosby maintained an estate. Andrea Constand, with whom Cosby had been acquainted for several years, claimed that during a visit to the estate, Cosby drugged her, and while she was unable to provide consent, he sexually assaulted her. During the next year, she continued to have telephonic and occasional personal contact with Cosby, but in January 2005, Constand, responding to her deep discomfort, confided to her mother the details of the incident. This set in motion a series of notifications to law enforcement and the district attorney of Montgomery County. Over the next month, an investigation ensued in which Constand was interviewed extensively, as was Cosby in the presence of counsel, during which he described a consensual encounter. At the conclusion of the investigation, the district attorney, troubled by the post-event behavior of Constand, which he considered at best odd or, worse still, inconsistent with a sexual assault when coupled with the absence of any physical or forensic evidence to corroborate the claim, concluded there existed insufficient evidence to successfully mount a prosecution of Cosby.

It was then that the district attorney embarked on an alternative course of action in an effort to provide Constand with some measure of justice. That “alternative path” was a civil action seeking monetary damages. To facilitate such a lawsuit, the district attorney publicly stated that no criminal prosecution would be commenced, thereby preventing Cosby from invoking his Fifth Amendment privilege against self-incrimination. Significantly, no non-prosecution agreement was signed by the parties, nor did they avail themselves of the statutory scheme by which “transactional” immunity is ordinarily conferred upon an individual by a court. Instead, a lengthy press release describing the district attorney’s decision, without mentioning any potential credibility concerns that had driven his declination of a prosecution, was drafted and released. Notably, at Cosby’s counsel’s request, the district attorney signed the release, making it the only memorialization of the parties’ understanding.

In the short term, the alternate path seemed to work exactly as it was conceived. Weeks later, Constand sued Cosby. Discovery led to four depositions of Cosby, who, with counsel present, did not invoke his Fifth Amendment rights and admitted to consensual sexual episodes with Constand and indicated that he had provided her with the antihistamine, Benadryl, to relax her. Additionally, while under oath, Cosby admitted that on other occasions in the past, he had provided women quaaludes prior to engaging in sexual intercourse. The parties settled the lawsuit with Cosby, agreeing to pay $3.38 million in damages with all records of the litigation and the terms of the settlement to be sealed.

For nearly a decade, the alternative path held. However, 2015 media requests to unseal the suit’s record were granted by the federal judge who had presided over the civil case. With Cosby’s depositions now public, the district attorney’s successor reopened the investigation and secured Constand’s cooperation, as well as that of several other women who claimed to have endured sexual assault by Cosby.

Just prior to the expiration of the commonwealth’s statute of limitations, Cosby was charged with three counts of “aggravated indecent assault.” Subsequent motion practice to dismiss the charges based upon the public declaration immunizing Cosby and to suppress his depositions based on his reliance upon the prior district attorney’s representations were all denied. The prosecution moved to adduce evidence of “Other Bad Acts of the Defendant,” which was comprised of testimony from other victims of Cosby. The trial court granted the application to the extent it permitted the testimony of only one alleged past victim.

In 2017, Cosby’s first trial – featuring testimony from Constand and another of Cosby’s alleged victims, as well as admissions culled from his civil depositions – ended in a mistrial, occasioned by a hung jury. Prior to the second trial a year later, the prosecution sought reargument of its Molineaux-type application, seeking to admit the testimony of 19 other women’s claims of sexual assault by Cosby, despite presenting no change of circumstance in support of the application. The trial court granted the application to the extent that it permitted the testimony of five witnesses – selected by the prosecution – and that the court would provide limiting instructions regarding such evidence to the jury. Cosby was convicted of all counts at the conclusion of his second trial and was sentenced to a term of three to 10 years’ incarceration, which was immediately imposed by the court. Additionally, Cosby was deemed by the court to be a “sexually violent predator.” Cosby’s appeal to Pennsylvania’s intermediate appellate court resulted in a unanimous affirmance.

The Supreme Court of Pennsylvania accepted Cosby’s appeal on two limited grounds: the first regarding the circumstances surrounding the commencement of the prosecution, years after the district attorney’s public statement describing an agreement on which Cosby relied to his detriment; and the second issue regarding the claimed abuse of discretion by the trial court in admitting such extensive uncharged crimes evidence.

The 79-page majority opinion reversed the conviction based upon Cosby’s reliance on the district attorney’s representation that no prosecution would ever take place. Although critical of the district attorney’s unorthodox procedure, and the court indicated that it was less than impressed that competent defense counsel had accepted such representations, the majority concluded that Cosby was denied due process by the entire chain of events, and he could only be made whole if the conviction was reversed and retrial was barred.

Two judges, concurring in part and dissenting in part, agreed that a due process violation had been inflicted upon Cosby, yet concluded that a retrial without use of the depositions or evidence gathered as a result was an adequate remedy.

A dissenting judge found that the questionable practice did not result in a due process violation. However, he did indicate that he was deeply troubled by the trial court’s abuse of discretion in permitting such extensive Molineaux-type evidence and would have reversed the conviction on this alternative ground, which was otherwise unaddressed by the court owing to it being rendered moot by the majority holding.

That this is a “hard case” is difficult to debate. That it results in “bad law” largely depends on the eye of the beholder. What is to be learned from the entire episode in examining the motivations for the participants making choices that resulted in such an unsettling conclusion? The authors will attempt to use the benefit of their experience to explain a case so characterized by a departure from all norms.

Why did the original district attorney decline to prosecute the case when he had a cooperative complainant and  instead embarked on the alternative path? Clearly, the district attorney concluded that Constand had been victimized. More than a year after the event, she was traumatized but did not satisfy the prosecutor that her explanations for her post-assault behavior would not undermine her credibility. And when compounded by the fact that she had civil lawyers on retainer, he was impressed that she could be easily portrayed as a “gold digger,” which would prevent a conviction and thereby subject her to the potential of additional trauma. Persuaded that she could not succeed in a criminal forum, the district attorney was certain she would succeed in a civil one, aware that “America’s Dad” – stripped of his Fifth Amendment privilege – would be forced to answer questions under oath that, if untrue, could result in a perjury prosecution, and if true, would incentivize him to generously settle the case to preserve his pristine image, if not his deep pockets. The propriety of a prosecutor insinuating himself into such considerations is hardly routine, and that it ended so poorly for everyone should not be surprising.

Why did the district attorney decide not to issue a standard non-prosecution agreement? Likely because Cosby’s receipt of such a document would have been devastating to his long-cultivated image. Such a formal writing would have created enough “smoke” to forever damage Cosby’s persona to the extent that no “fire” would have been needed.

Why did the parties elect not to avail themselves of the commonwealth’s statutory scheme requiring judicial intervention for a grant of immunity? Surely, no one wanted to answer the question any judge entertaining such an application would pose: “Have you discussed this with the victim?” Were a public proceeding to occur at which the victim contradicted the district attorney, a prosecution that neither party wanted was likely to result. For the alternate path to work, the less said was obviously better.

Why did the successor district attorney proceed with such a tenuous prosecution? Obviously, the subsequent depositions revealed the scope of Cosby’s behavior and the dimension of his criminality, and the passing decade and the advent of the #MeToo movement made the paternalistic decision that the victim would be additionally wounded less supportable.

The choices thrust upon defense counsel and the avenues selected are equally vulnerable to the critical analysis, so easily invited by hindsight. For Mr. Cosby’s counsel, that this was a “hard” case was clear. His celebrity status not only compounded the risks faced by the client but resulted in the stark reality of the imperfection of any advice that could be provided to the increasingly vulnerable Cosby. Therefore, counsel was forced to represent a client in separate and distinct courts – a court of law, both criminal and civil, as well as in the “court of public opinion,” the one in which his fortune was made, in which his reputation had been carefully honed, and in which judgment could be even more harsh and without any avenue of appeal. Accordingly, counsel was compelled to devise strategies for competing interests – sparing Cosby criminal conviction, while simultaneously stage-managing a previously unassailable reputation and public image. It is because these interests are at times antagonistic that devising a strategy that addresses all of his client’s vulnerabilities is so daunting. However, counsel must always remain vigilant to prioritize the client’s vulnerabilities in charting the strategy that will be deployed. Counsel must be careful not to be seduced by the client’s desire to focus exclusively on the court of public opinion. For pursuing victory in that court may set the stage for catastrophic results at the real courthouse.

Emblematic of the competing interests faced by Cosby’s counsel are the elections made from the earliest moments of this odyssey in 2005. Immediately, counsel was challenged by the dilemma posed by “two court representation.” Constand made allegations of sexual assault against Cosby. Law enforcement quickly corroborated several details of her claim. Her mother provided some weight to the accusation with “outcry evidence.” Telephone records, financial records and travel histories provided powerful support for the details of the accusation, certainly proving that a significant opportunity and means for the crimes existed. It was at that stage that law enforcement invited Cosby to participate in an interview, a critical juncture for all sides in the investigation of charges as serious and sensational as these.

Usually, counsel is appropriately reluctant to allow a client to sit for an interview with prosecutors and investigators. Unless counsel has information that conclusively establishes the client’s innocence, the remaining alternative is a complete denial of culpability, something that will do little to dissuade a prosecutor from bringing charges. And the cost of advancing a passionate denial is the likely admission, in counsel’s presence, of corroborating details of the alleged crime, such as location, occasion and means, all of which can be skillfully utilized in a subsequent grand jury presentation or trial.

Ordinarily, best practices would dictate that counsel decline the invitation to have the client interviewed. But Cosby’s counsel and Cosby himself were clearly worried about the court of public opinion. The media’s demand to hear “his side of the story” far outweighed the legal niceties of one’s Fifth Amendment right against self-incrimination or the sanctity of the presumption of innocence. Where in a court of law, maintaining one’s silence increases one’s odds of acquittal, in the court of public opinion it is certain to result in a verdict of guilt. In the case of a celebrity of Cosby’s stature, such a verdict at that time seemed every bit as devastating as a conviction after trial. It is apparent to the authors that it was this calculus that drove counsel’s decision to permit Cosby’s interview and, because it was not based on purely legal considerations but rather concerns related to public relations, it contributed mightily to the result.

Perhaps more subtle, but as significant, was the conundrum faced by counsel when the district attorney concluded that a conviction of Cosby could not be obtained, despite the unsettling facts unearthed during the investigation. Normally, such a decision by a prosecutor is music to the ears of defense counsel. After all, criminal liability and the threat of conviction and sentence have been removed. But in the absence of a formal agreement, how binding was such a decision? What if new evidence came to light? Or new accusations? Or ancient claims of a similar nature? Moreover, with the threat of prosecution removed, and Cosby forced to be deposed during a civil case, no protection from criminality for matters outside Montgomery County was forthcoming. Again, counsel’s acceptance of an informal, signed press release as sufficient protection against criminal liability appears to have been driven by strategies to achieve a long-term victory in the court of public opinion, rather than a permanent solution to his increasing criminal exposure. That Cosby was possessed of unlimited financial resources to buy both settlements and silence surely made these decisions seem less dangerous and more appealing to the client and less worrisome to counsel.

Pursuit of a public relations victory by emphasizing the jeopardy faced in the court of public opinion resulted in Cosby’s damning admissions regarding a legion of abused women and his resort to drugging some with quaaludes as part of his modus operandi. And, as is now clear, it was this litany of admissions and roster of victims that ensured Cosby’s conviction, incarceration and ultimate disgrace. Sound legal judgment supported none of these decisions. Rather, the sad recognition that use of one’s right to silence – a criminal suspect’s best friend – when embraced in the court of public opinion, is the equivalent of an admission of guilt, and that reality influenced Cosby’s representation more than reliance on tried-and-true criminal practice norms.

That the entire house of cards collapsed is not surprising. That experienced and competent counsel advised Cosby throughout is unquestioned. One can only speculate that counsel desperately attempted to dissuade the fabulously successful and wealthy client from countenancing such pronounced legal risk. It is not difficult to imagine a version of the following conversation taking place between the exasperated attorney and the pampered, self-absorbed celebrity client:

LAWYER: “Pal, you have to take the Fifth. You’ve got big trouble and you can get badly hurt!”

CLIENT: “But then everyone will think I’m guilty.”

LAWYER: “I hate to tell you this, but everyone already thinks that you are guilty. All they need is for you to answer their questions to prove it.”

CLIENT: “But that will look terrible in the press.”

Indeed, it would. But history demonstrates that the answers look even worse in a court of law than in the court of public opinion and contributed mightily to this remarkable legal morality tale.

Because the authors have spent their careers as advocates and have never served as judges, we are reluctant to speculate regarding the basis for the trial court’s exercise of discretion and the reconsideration of such significant rulings. However, all practitioners are aware that courts are not only tasked with the fair administration of justice but also with responsibility that the process appears to yield a final product that the public will embrace as a fair one. The oft-expressed notion that the quality of justice for the wealthy and influential is different from that afforded the “common man” is of great concern to all of us, but particularly to the judiciary. In a case involving a public figure as well-known and revered as Cosby, with evidence so compelling, including his well-publicized admissions under oath of repulsive deeds, a test of the fundamental fairness of our justice system was certainly framed by the media. It is understandable that such considerations might influence any of us and result in discretionary rulings outside what we would ordinarily expect.

In conclusion, the proposed addendum to our time-honored maxim about “hard cases” – that “celebrity cases make worse law” – has enormous support in this entire, sad adventure. Because of the celebrity of the accused, who was suspected of unspeakable crimes based upon evidence that was less than overwhelming, a recipe of unique decisions replaced all routine practice by everyone involved in the matter. In retrospect, each unorthodox decision is understandable considering the difficulties presented but, in combination, the serial abandonment of norms and standard practice resulted in a saga littered with “what might have beens.”

Had the original district attorney engaged in a more thorough, extensive investigation of the original charges in 2005 and found some of the Molineaux-type evidence subsequently adduced more than a decade later and elected to provide a crime victim her day in court, rather than so quickly opting to pursue an alternative path after only three weeks of review, might things have ended differently? If the same prosecutor determined that it was not his place to insinuate himself into a potential civil suit between the parties and followed the time-honored prosecutorial consideration of simply determining whether sufficient admissible evidence existed to establish that a crime had been committed by an identifiable individual – regardless of the celebrity of that person – what might have been the result? Had the procedural statutes been followed requiring judicial intervention before insulating a suspect from criminal liability, would anything have changed? If defense counsel insisted on a formal non-prosecution letter from the district attorney prior to permitting Cosby to answer the damning questions posed during his civil deposition, what might have happened? Or still, because of potential criminal liability extending beyond the border of Montgomery County, if Cosby, pursuant to the advice of counsel, continued to invoke the Fifth Amendment, what would have transpired? Would different answers to these questions and so many others as the result of the parties making decisions grounded in established criminal practice have influenced the trial judge to make different rulings that were more likely to be sustained on appeal?

Of course, we can never know the answer to any of these imponderables. But what does appear to be reaffirmed is the notion that the “best practice” is the familiar practice. That when good lawyers start handling a case differently, based upon considerations that are foreign to their standard practice, no one should be surprised when an unexpected and dissatisfactory result punctuates everything that the lawyers have done.


David Louis Cohen is the current Chair of NYSBA’s Criminal Justice Section. His practice consists primarily of representing those accused of crimes in both federal and state courts. He currently is a member of NYSBA’s Executive Committee, the Committee on the State Constitution and the Legislative Policy Committee. Cohen was a member of the New York State Assembly and was counsel to Assemblyman Joseph R. Lentol, Chair of the Assembly Codes committee.

Robert J. Masters currently serves as a special assistant district attorney to Rockland County District Attorney Thomas E. Walsh II. From 1990 until 2019, he worked in the Queens County District Attorney’s Office, working primarily on homicide prosecutions and eventually serving as an executive assistant district attorney for legal affairs and as counsel to the late District Attorney Richard A. Brown. Previously, he served as a law clerk for various judges of the criminal term of the Supreme Court in both Queens and Kings County. Masters also served as Chair of the Criminal Justice Section.

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