Judge Jed S. Rakoff caused a stir in 2011 when he rejected a $285 million settlement between the Securities and Exchange Commission and Citigroup over the bank’s handling of mortgage investments leading up to the Great Recession. Dissatisfied with a sum he considered “pocket change” for the multibillion-dollar bank, he admonished the SEC for leaving “defrauded investors substantially short-changed.” Further rankled by Citigroup’s refusal to acknowledge any wrongdoing, Rakoff characterized the settlement as unfair, inadequate and antithetical to the “public interest.” This pronounced denunciation of the government’s failure to prosecute those responsible for the 2008 financial crisis, combined with his refusal to rubber-stamp the settlement, made Rakoff a media darling. His peers, however, didn’t share these views: Construing a narrower role for the courts, an appellate panel quelled his inchoate revolt months later.

The setback hasn’t stopped Rakoff from continuing to air his frustrations with the criminal justice system. Presiding over several high-profile white-collar cases has made him well positioned to condemn the evasion of justice by well-heeled companies and their executives. In “Why the Innocent Plead Guilty and the Guilty Go Free: And Other Paradoxes of Our Broken Legal System,” Rakoff reaches far beyond corporate boardrooms to highlight an array of shortcomings within the criminal justice system. His proposed fixes are worthy of consideration but also lay bare a harsh reality: The entrenched interests tolerating the system’s inequities and, in some cases, profiting from the status quo pose significant obstacles to reform.

Rakoff realized that America’s “system of justice is failing its mission” after becoming a federal district court judge a quarter-century ago. What’s the nature of this failure? The country imprisons millions of indigent Americans yet routinely allows white-collar criminals to avoid punishment. Rakoff offers multiple explanations for this predicament but contends that the “diminishment in the power of the courts” is a key factor in the failure to rectify these injustices — a concept he returns to throughout the book.

Noble intentions paved the road to mass incarceration. Desperate to counter the crime wave of the 1960s and ’70s, legislators targeted nonviolent offenses, mandated long sentences, severely punished recidivists and reduced the role of the judiciary. These policies bore unintended consequences. Today, America spends approximately $180 billion annually to operate its law enforcement agencies, courts and prisons amid the nation’s crumbling infrastructure, lagging education system and underfunded public pensions. The human toll is far worse. Despite plummeting crime rates — murders in New York City dropped by nearly 80 percent from 1990 to 2020, for instance — the United States houses one-quarter of the world’s prison population, which is disproportionately African American. The fact that 1 in 9 prisoners is serving a life sentence contributes to these swelling figures.

Though social scientists haven’t been able to determine whether mass incarceration reduces crime, Rakoff argues that the public has shown little appetite for an overhaul. Most people, he writes, “are reluctant to tamper with the laws they believe made them safer.” If last year’s uptick in murders persists, it will probably suffocate any chance for reform.

Perhaps nothing contributes more to mass incarceration than plea bargaining. With high mandatory sentences as a cudgel, prosecutors pervasively threaten defendants with draconian charges that could lead to years of imprisonment. As a result, only 2 to 3 percent of cases go to trial and about 9 to 10 percent of innocent defendants are coerced into pleading guilty, according to the National Registry of Exonerations and the Innocence Project. The practice is far more common among poor defendants, who lack the resources to counteract a prosecutor’s built-in advantages. In spite of these flaws, most judges have accepted the widespread use of plea bargains to reduce their hefty caseloads, and the Supreme Court has blessed the practice.

Consistent with his expansive vision of the judiciary’s role, Rakoff proposes empowering magistrate judges, who assist federal district courts, to oversee plea bargains, injecting an unbiased voice into the process and altering the power dynamic between prosecutors and defendants. He would also require prosecutors to periodically represent indigent defendants so they could appreciate the “one-sided nature of the . . . plea-bargaining process.”

Just like his criticism of plea bargaining, the book’s most compelling moments cast doubt on widely held assumptions about the justice system. Rakoff’s revelation of the misplaced faith in witness testimony and forensic evidence outside of DNA, which he considers the gold standard, is eye-opening. The overreliance on these policing tools has wrongly imprisoned far too many Americans: One study of 2,400 false convictions found that 40 percent of these cases included “erroneous eyewitness evidence” and that 25 percent included “false or misleading forensic evidence.”

Unconvinced by the government’s excuses since the Great Recession, Rakoff is equally vexed by the failure to prosecute corporate wrongdoing, a criticism he has reiterated during his tenure on the bench. “To a federal judge,” he declares, the government’s reluctance to hold executives accountable and instead enter into “cosmetic prosecution agreements” with corporations that are repeatedly violated and unenforced “is disturbing . . . in what it says about the DOJ’s apparent disregard for equality under the law.” Rakoff fittingly cites Pfizer to exemplify his point. The four deferred-prosecution agreements between the pharmaceutical giant and federal authorities from 2002 to 2009 — all devised to prevent future misconduct — failed to stop the company from flouting the law. Through it all, Pfizer’s executives went unpunished, and the fines the company paid represented a fraction of its ill-gotten gains.

The one hiccup in this pithy and persuasive work is a detour denouncing the broad scope of presidential authority. It is a brief diversion from the question at the heart of the book: Rakoff may paint a convincing picture of a broken and unfair criminal justice system, but will others sign on to his proposals? Making sweeping changes to plea bargaining, downgrading the emphasis on forensic evidence and eyewitness testimony, and reducing prosecutorial discretion have little traction among law enforcement groups and political leaders. Though few judges have joined Rakoff’s push for reform, his message to fellow jurists is more likely to resonate: “Unless we judges make more effort to speak out against this inhumanity,” he asks his colleagues, “how can we call ourselves instruments of justice?”

Why the Innocent Plead Guilty and the Guilty Go Free

And Other Paradoxes of Our Broken Legal System

By Jed S. Rakoff

Farrar, Straus and Giroux.
193 pp. $27