Sentimental Judgments

Upon learning of the first proposal for a graduated income tax, 18th-century French finance minister Anne-Robert-Jacques Turgot remarked that it would be wiser “if we executed the author, not the project.” Similarly, the majority of proposals in Judge Jed Rakoff’s survey of criminal and constitutional law, Why the Innocent Plead Guilty and the Guilty Go Free, ought to remain just those: proposals not policies.

The slim 178-page book is a collection of essays Rakoff initially published at the New York Review of Books. Rakoff, a federal judge who has taken senior status from the Southern District of New York, walks readers through what he views as noteworthy ills of the modern American legal landscape and his proposals to remedy them. To be sure, his chapters on the underenforcement of white-collar crime and the overemployment of plea bargaining are quite informative. However, three subjects, on the incarceration of criminals, the death penalty, and detention of accused terrorists, are misplaced targets of Rakoff’s ire. They exemplify an unfortunate trend throughout the book: one missed opportunity after another opportunity to convince anyone who might disagree with him.

Criminal Incarceration

Rakoff trains his focus in the first chapter on what he calls “The Scourge of Mass Incarceration.” As crime in America has fallen since the early 1990s, incarceration levels remain the same or higher. Rakoff blames the popularity of “tough on crime laws” passed from the 1960s-1990s and those laws’ mandatory minimum sentences as drivers of incarceration rates. He argues, “Americans, having noticed that the crime-ridden environment of the 1970s and 1980s was replaced by the much safer environment of today only after tough sentencing laws went into force, are reluctant to tamper with the laws they believe made them safer.” The long-term cost of such incarceration results in not only additional expenditures, but also “wasted lives, devastated families, and racial bias.”

Rakoff’s solution addresses the sentencing element, championing both legislation and “brave” judging. He praises the First Step Act, which became federal law in 2018, for its retroactive reductions in mandatory minimum sentences. He also applauds those federal judges who call attention to how sentencing guidelines contribute to “mass incarceration.” To Rakoff, judges abdicate their role in discerning sentences when they follow sentencing guidelines rather than devising sentences themselves. Rakoff believes leadership among “those whom the public does respect” can break the impasse in deference to sentencing guidelines and mandatory minimum sentences.

Recent events, however, undermine Rakoff’s contentions. As Rakoff seeks to reduce sentences and return convicted criminals to civilian life, 2020 featured one of the starkest year-over-year increases in crime in American history. Heather MacDonald reports that “the local murder increases in 2020 were startling: 95% in Milwaukee, 78% in Louisville, Ky., 74% in Seattle, 72% in Minneapolis, 62% in New Orleans, and 58% in Atlanta.” Rakoff’s idea that at present “brave” judges should begin more aggressively defying the citizenry’s input on mandatory minimums while facing stark increases in crime seems ill-timed.

But even if judges do not act, the effective erasure of mandatory minimums is already occurring in some of the nation’s largest cities. The leadership Rakoff pines for has been evident in progressive local prosecutors such as Larry Krasner, the district attorney of Philadelphia since 2017. Andrew McCarthy details that Krasner addressed the problem of mandatory minimum sentencing guidelines by “engag[ing] in fictional ‘fact-pleading’—pretending, at the charging or pleading stage, that the offense did not occur, or reimagining it into vanilla crime. In so doing, Krasner’s people erase indicia of violence, firearms, drug-weight, and other factors that trigger statutory minimums.” Rakoff does not comment on the tactics of these local district attorneys in the book, though he does believe that state mandatory minimum laws ought to be “repealed or at least moderated.” However, even in these overwhelmingly progressive cities, many citizens have begun pushing back. The experience of newly elected progressive district attorneys Chesa Boudin in San Francisco and George Gascon in Los Angeles is instructive. Less than two years into their tenure as district attorneys, both Boudin and Gascon face recalls.

Death Penalty

But Rakoff’s most one-sided chapter centers on the death penalty. Throughout the chapter, he misses opportunities to address overlapping concerns with supporters of the death penalty while also offering sweeping moral claims without any reference to genuine counters to those claims.

Rakoff is as strong a critic as possible of the death penalty as a federal judge. In one 2002 ruling, he declared the federal death penalty unconstitutional on the grounds that “under the due process clause of the Constitution, an innocent person never loses his legal right to prove his innocence, but that he has been effectively deprived of that right if he is executed.” Rakoff acknowledges his ruling was an attempt to “deprive the death penalty of its moral force and its ultimate justification.” Contra Justice Oliver Wendell Holmes, Rakoff understands law and morality as inextricably linked. This understanding is persuasive. The problem for Rakoff though is that he makes attenuated claims on the immorality and illegality of the death penalty.

First, if Rakoff is correct that emerging technologies in DNA testing yield far greater insights into evidentiary reliability, these insights do no more to negate the morality or legality of the death penalty in principle than any previous improvements in evidence gathering. Even if precise DNA testing is considered the gold standard at present, the past introduction of fingerprinting and audio and visual recordings improved the quality of evidence from previous standards. In practice, the availability of any new technology counsels prudence in applying the death penalty in cases where evidentiary doubts exist. Improvements in DNA testing could improve the quality of evidence for accused and convicted criminals. The availability of these improved DNA testing regimens will depend on many contingent factors, cost of time and money among them. However, in principle these improvements in technology do not implicate the death penalty. The legality and morality of the death penalty in a case where no doubt exists, say the gunman who killed nine churchgoers in Charleston, South Carolina in 2015, do not depend on the latest advances of DNA testing.

Next, in telling an emotional story about his brother’s brutal murder and his moving on from his initial desire to see the death penalty meted upon his brother’s killer, Rakoff unfortunately fails to articulate the retributivist case for the death penalty either for his brother or for those who sought justice in Charleston. For example, In Eichmann in Jerusalem, Hannah Arendt powerfully argued in the context of the Holocaust that someone may do something so evil that no one should share the earth with that person. Relatedly, legal scholar Hadley Arkes writes on the importance of retributive justice, “It makes a profound difference when we don’t begin by ruling out capital punishment in those ‘smaller murders’… For what we are saying then is that we take those lives quite as seriously, we attach as much importance to them, as to the lives of those uncles and aunts, grandfathers and grandmothers, who died in the Holocaust.” Instead, in a regrettable blind spot, Rakoff fails to acknowledge that the retributivist case explains as much support for the death penalty as his claims that the death penalty is a symptom of “systemic racism.”

Furthermore, Rakoff’s absolutist views on the death penalty screen out a compromise that seems within grasp. Majorities of Americans still favor the death penalty, even if less strongly than in previous years. Rakoff surmises that support for the death penalty has fallen due to generally falling crime and murder rates (until recently) along with improvements in DNA testing. Nevertheless, the popular desire to preserve the death penalty is strong. If Rakoff’s goal is to lessen the disproportionate imposition of the death penalty on black men with questionable evidence against them, then a stronger endorsement of the death penalty only for especially egregious cases with the least amount of doubt about guilt makes more sense than an attenuated claim that the death penalty is prima facie immoral and unconstitutional.


Rakoff reserves some of his harshest rhetoric for his chapter on the treatment of detainees in the War on Terror. As with his chapter on the death penalty, his analysis fails to address some of the most elementary criticism from those who might disagree with him. A more thorough examination of the separation of powers would improve Rakoff’s analysis.

“It is a historical fact that when the word ‘war’ is uttered,” Rakoff starts, “the rule of law often implodes, with courts frequently employing sophistry to avoid any interference with government conduct.” Rakoff decries the treatment of detainees under the War on Terror, particularly those detainees held at Guantanamo Bay, Cuba, as violative of the U.S.-signed United Nations Convention Against Torture. In a personal crusade of his, Rakoff stresses that even as the Guantanamo detainees won the right to petition for a writ of habeas corpus for their release, such a victory is a “hollow reed.” Lower courts and also the Supreme Court have denied them practical relief by refusing to advance lawsuits that would secure their release. Rakoff sees this effectively indefinite detention as without precedent, and the federal courts its timid handmaiden: “The government will always use the excuse of war to take authoritarian measures that no other excuse could hope to justify.”

But what if federal judges are not so much timid as rather concerned about the separation of powers and their own institutional capacity and expertise? Rakoff bemoans the judiciary’s “hands-off approach to dubious practices associated with the war on terror.” Yet, this “hands-off approach” draws upon the logic underlying the separation of powers. Federal judges, with their role confined to specific cases and controversies, lack not only the institutional competence but also the accountability to determine the course of our national defense. As I have written in these pages, the executive’s duty of “maintaining a sovereign defense… is never ‘out of session’ as a legislative or judicial body often are.”

Although the War on Terror’s uniquely amorphous understanding of a semi-permanent state of war provides Rakoff with firmer ground, the War on Terror’s uniqueness does not provide license for the judiciary to perform a neat inversion of its role in the separation of powers. Judges, under Rakoff’s preferred scheme, then would become “prime arbiters” of the measures justifiable in protecting the people from external threats. This is a role unfit for officeholders unaccountable to the national electorate due to life tenure. In turn, Rakoff would shift “executive responsibility from maintaining the safety of citizens to maintaining the due process ‘rights’ of non-citizens.”

Why the Innocent Plead Guilty and the Guilty Go Free could have been a more thoughtful and nuanced book, taking more seriously the sharpest criticism of its core positions. However, that book would have been necessarily longer than 178 pages. With a dismissive attitude toward much potential criticism, Rakoff kept his book a quick read. However, he sacrifices persuading those who might disagree with him.

This article was originally published at Law & Liberty here.

Garrett Snedeker is the Deputy Director of the James Wilson Institute and a J.D. student at the Antonin Scalia Law School.
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