Aggressively Defending My Clients Since 1990

There hasn’t been a criminal defense lawyer on the Supreme Court in 25 years. That’s a problem.

On Behalf of | Mar 30, 2019 | Firm News

By Dara Lind[email protected] Updated Mar 22, 2017, 10:54am EDT

It’s been a quarter-century since a former criminal defense lawyer sat on the Supreme Court.
Since then, crime has fallen by half. Incarceration has risen, then fallen (slightly) again. Americans are becoming more and more critical of the “tough-on-crime” mindset that defined the end of the 20th century, and more skeptical that police and prosecutors will always use their powers for good — in other words, they’re coming in line with how defense lawyers see the world.
But if Supreme Court nominee Neil Gorsuch is confirmed by the Senate — as he’s likely to be — the court will have three ex-prosecutors. It will have zero former criminal defenders.
Appellate defense lawyer Timothy O’Toole points out that the Court has veterans of both sides of civil cases (defendants’ and plaintiffs’ lawyers) and one side of criminal cases (prosecutors). “But the one group that seems kind of outside that box, particularly on the Supreme Court, are defense lawyers. And that’s a shame.”
Defense lawyers and scholars worry this isn’t an accident; it’s the result of the structure that shapes who can get nominated to the Supreme Court to begin with. Federal judges tend to be people who “ticked all the political checkboxes on their career starting from when they were 15,” says Tejas Bhatt, assistant public defender for New Haven, Connecticut. Often one of those boxes is working as a prosecutor.
Even beyond any particular career experience, the system rewards “people who don’t take controversial positions, they don’t do controversial things, who don’t issue controversial opinions, who do seem to hew more toward law and order and enforcement.”
Chip Somodevilla/Getty
There’s good reason to be concerned about the jurisprudence of a court that only understands one side of a criminal case from experience — and since the high-water mark of the 1960s, defense lawyers have seen the Supreme Court put serious restrictions on the right against self-incrimination, the right against unreasonable search, and even the right to a lawyer.
But to many of them, this isn’t just a problem with jurisprudence. It’s a problem with the Supreme Court in a democracy — and in an increasingly diverse America. They believe the politics of Supreme Court confirmations has limited all but a very narrow, very privileged slice of America to have a shot at a seat on the highest court in the land. And one of the groups who they fear are locked out is the people whose job it is to stand up for the rights of the marginalized — and those who are on the wrong side of well-intentioned laws.
The dangers of a prosecutor-friendly Court
Here’s what’s at stake. A large swath of the Bill of Rights is dedicated to protecting suspects in criminal investigations and defendants in criminal trials: the right against unreasonable search in the Fourth Amendment; the right against self-incrimination and the right to due process in the Fifth Amendment; the right to a jury trial and a lawyer in the Sixth Amendment; the right against cruel and unusual punishment in the Eighth Amendment.
In theory, how far these rights really extend is a matter of constitutional interpretation — transcending justices’ personal sympathies (for victims of crime, for the accused, for prosecutors) or their feelings toward the criminal justice system in America today.
In practice? Nah.
In 2005, Boston University law professor Ward Farnsworth suggested that how much a justice thought the Constitution protected defendants relied more on how the justice felt about defendants than how she felt about the Constitution.
By analyzing decisions in criminal law cases from 1953 to 2002 — separating cases in which people claimed their constitutional rights had been violated from other criminal cases (involving, say, the interpretation of a federal law or a procedural rule) — Farnsworth found a pattern.
In non-constitutional cases, where the disagreements were largely about policy, some justices consistently sided with the prosecution and others consistently sided with the defense. That’s predictable enough — some judges (often conservative) tend to favor law and order, while others (often liberal) tend to be skeptical of law enforcement.
But the same thing happened in cases where, in theory, the justices were disagreeing about constitutional rights. Justices who sided against defendants in policy cases also tended to see their constitutional rights as narrower. Justices who sided with defendants in policy cases tended to agree that their constitutional rights were more expansive too.
If you’re already used to thinking of Supreme Court justices as political actors, this correlation isn’t surprising. But that doesn’t mean it’s not important. Over the past half-century, we’ve seen how much the Court’s interpretation of the rights of defendants can vary — and how much it matters.
Justices who served on the Supreme Court during the 1953-2002 period. Empty circles reflect how often the justice voted for the government (i.e. the prosecution) in cases involving constitutional questions; filled-in circles represent how often she voted for the prosecution the rest of the time. Ward Farnsworth/Michigan Law Review
Fifty years ago, under Chief Justice Earl Warren, the Supreme Court gave us the right to a public defender as we know it (Gideon v. Wainwright). It gave us the idea that a suspect must be told of his right to remain silent (Miranda v. Arizona). It gave us the rule that any evidence obtained under an unconstitutional search — even if it proves the defendant’s guilt — is prohibited from being entered in court (Mapp v. Ohio). It gave us the requirement that if the prosecution discovers evidence that might prove the defendant wasn’t guilty, it has to turn that evidence over to the defense (Brady v. Maryland).
But in the decades since, the Court has eroded those rights.
Defendants now have to declare that they’re invoking the right to remain silent in order to end questioning. The right to a lawyer has been (in the eyes of some) compromised, as the Court has given the government more power to seize bank accounts that could be used to pay for defense. And the right to exclude illegally obtained evidence has been rendered less meaningful, as the Court has carved out more and more exceptions for police to engage in searches and surveillance without a warrant.
As Farnsworth found, ideological sympathies definitely shape constitutional jurisprudence — and personal experience shapes ideological sympathies. The concern of a prosecutor-stacked Court is that its members might be too likely to zero in on the guilt of the defendant, and forgive the methods used to catch him.
But working as a prosecutor doesn’t automatically flip a switch and make someone permanently more sympathetic to prosecutors — just look at former prosecutor Chief Justice Warren himself. Or just look at the two former prosecutors currently on the Court — Justice Samuel Alito and Justice Sonia Sotomayor.
The Court’s current ex-prosecutors see the law in very different ways
“Having experience as a prosecutor probably tells you something about where people’s values were when they decided to get a job as a lawyer at the beginning,” says O’Toole.
In the case of Samuel Alito (who’s been on the Court since 2005), that’s abundantly clear: Alito once wrote on a job application that his interest in the law had been inspired by his disagreement with the liberal, pro-defendant decisions made in the 1960s by the Warren Court.
He’s certainly made his dissatisfaction felt — by helping roll back many of those decisions.
Alito wrote the 2013 opinion Salinas v. Texas, which said that the defendant had to explicitly say he was remaining silent in order for it to count. Where the Warren Court limited the police’s ability to obtain evidence in searches, Alito wrote the 2014 opinion Fernandez v. California — which ruled that it was legal for police to search a residence even if one of the occupants objects, as long as that occupant isn’t around (i.e., he’s already been arrested).
“Alito quite clearly has a disdain for people who are on the other side of crime, and a lack of respect for people who are defendants in the criminal justice system,” says appeals court defense attorney Matt Kaiser.
If Alito is evidence that “once a prosecutor, always a prosecutor,” the Court’s other former prosecutor, Sonia Sotomayor, represents an alternative that O’Toole and other lawyers say is common: judges whose experience as prosecutors leads them to have a more realistic, tempered view of law enforcement.
Thanks to what law professor Tony O’Rourke calls a “healthier appreciation of, let’s say, the diversity of professionalism” among police and prosecutors in the field, Sotomayor is arguably the most pro-defendant justice on the current Court.
When other justices ruled that a suspect had to explicitly say, “I want to remain silent,” to keep his Miranda rights in a 2014 case, Sotomayor pointed out: “The Miranda warnings give no hint that a suspect should use those magic words, and there is little reason to believe police — who have ample incentives to avoid invocation — will provide such guidance.”
The members of the Supreme Court meet with President Obama in 2009, prior to Justice Sonia Sotomayor’s swearing-in. Pete Souza/The White House via Getty
O’Rourke points out that while Sotomayor and Alito were both prosecutors, they weren’t the same type of prosecutor. “Justice Sotomayor cut her teeth in the Manhattan District Attorney’s Office,” he says. “She’s used to dealing with the realities of a relatively resource-constrained prosecutor’s office, as opposed to, say, a US attorney’s office.” In other words, she’s used to criminal investigations that are constrained not just by rules, but by the logistical realities of a broad caseload and a sometimes less-than-professional police force.
Alito, on the other hand, “was in a US attorney’s office in a relatively elite district.” His police force — the FBI — was a fairly professional one. So the things that kept him from doing his job the way he wanted to do it were, O’Rourke says, “the internal policies and practices of the US attorney’s manual.” It makes sense that he’d regard those as unwelcome bureaucratic constraints.
But of course, the fact of the matter is that Sonia Sotomayor and Samuel Alito weren’t identical people before they started their respective law careers. Sotomayor’s experience as a prosecutor is layered on top of her experience as a Latina from a working-class family. Her background is more similar to some of the defendants than to that of other justices on the Court.
That matters. Like it or not, the justices are more concerned about constitutional overreach by law enforcement when they can imagine themselves, or people like them, as the targets.
Rachel Levinson-Waldman, a privacy expert at the Brennan Center for Justice, argues that this explains a few recent decisions the Court has made restricting law enforcement’s use of technology.
Cellphones: Even affluent white people use them! Win McNamee/Getty
Previously, she says, the Court had ruled that individuals couldn’t expect privacy from law enforcement when doing anything in public (say, driving around). But in 2012, the Court ruled that attaching a GPS device to a suspect’s car qualified as a police search under the Fourth Amendment.
“One of the things that changed the justices’ mode of thinking,” Levinson-Waldman says, “is, ‘Wait a minute, these GPS devices could be put onto our cars if the government’s theory is right.’ That’s when it started to seem very personal.”
Something similar happened in 2014, when the Court ruled that police couldn’t search a suspect’s cellphone without a warrant: Justices “went, ‘I have a cellphone, I have an iPhone,'” Levinson-Waldman says.
“But these surveillance technologies don’t just come into existence when they affect the lives of basically wealthy, highly educated, highly powerful people,” she continues. “They are used far before that. They’re used first on marginalized communities, they’re used on communities of color.” They’re used on people in whom only Sotomayor might recognize herself.
The system that encourages would-be Supreme Court justices to start planning out their careers at the age of 15 doesn’t allow for many Sonia Sotomayors. They’re more likely to be “the 1 percent of the 1 percent,” says Bhatt.
Only people from elite backgrounds are likely to know at a young age that there’s a fairly established career path for the federal judiciary: “Go to a prestigious law school, work at some big white-collar firm, go to the US attorney’s office, put in my time there, and then get nominated to the bench.” And their risk-averse route doesn’t allow them to come into contact with the people who tend to rely on the Bill of Rights’ criminal protections the most.
Former prosecutors assume all prosecutors are as scrupulous as they were
The problem isn’t that mediocre prosecutors get rewarded with federal judgeships, much less slots on the Supreme Court. It’s the opposite.
Ex-prosecutors who make it to the Supreme Court — the Sonia Sotomayors, Samuel Alitos, and perhaps Neil Gorsuchs of the world — were only the best, most scrupulous prosecutors. That creates its own failure of empathy.
“Here’s the core problem,” says Kaiser, the criminal appeals lawyer. “When prosecutors are on the Supreme Court and they’re making rules about criminal cases, and they’re making rules about what prosecutors are supposed to do, they think about themselves when they think about people following those rules.”
Those blind spots become most apparent when the Court is presented with a case where prosecutors try to use the Supreme Court’s own rules as a way to gain the upper hand.
Earlier this year, the Supreme Court took a case out of Louisiana regarding the Warren-era precedent Brady v. Maryland, which established that it’s illegal for prosecutors to withhold evidence if it would change the outcome of a trial. When prosecutors violate Brady, and that gets found out later, the conviction is often overturned.
The Supreme Court in 1962, the height of the defendant-friendly era presided over by Chief Justice Earl Warren. Hulton Archive/Getty Images
In the eyes of many Supreme Court justices, the point of Brady is to ensure that prosecutors see it as their job to turn over potentially exculpatory evidence. In the eyes of many prosecutors, though, the point of Brady is that it gives them a step-by-step guide to when they do and don’t have to turn over evidence.
The Louisiana case showed just how far apart those perspectives really are. In oral arguments, the lawyer for the Louisiana prosecutors admitted that “a prudent prosecutor would have” told defenders that one of the key eyewitnesses at the trial had initially told police he couldn’t identify the perpetrators. But the lawyer argued that just because the prosecutors were imprudent didn’t mean they’d violated Brady — because the prosecutors believed that the evidence wouldn’t have changed the case’s outcome, and that meant they were in the clear.
As defense lawyer Bidish Sarma wrote on the American Constitution Society blog, “[S]everal Supreme Court justices appear genuinely shocked to hear that prosecutors rely upon Brady […] to decide before trial whether to turn evidence over to the defendant.” They assume that Brady is about a deeper ethical obligation — because that’s the obligation they, as prosecutors, would feel.
“If you have a bunch of people who are assuming that prosecutors are in every case diligent and zealous about making sure they meet both the spirit and the letter of their constitutional obligations,” says Kaiser, “and then you have a bunch of people who think Brady is a game where they can withhold evidence to secure their conviction, they’ll just have rules that hurt defendants.”
Defense lawyers are already “attuned” to the dispossessed
Obviously, the problem of Supreme Court justices seeing the law as it should be practiced, rather than as it actually is, is something too deep for any president to fix with a single appointment. But Kaiser and others point out that cases involving evidence under Brady, for example, might be a lot easier to resolve if anyone on the Court had had experience using evidence to assemble a defense.
“When you see former defense lawyers write on or rule on those issues from the trial bench, it’s not an imagination game; it’s an experience game,” says Timothy O’Toole. “You’ve got somebody who’s formulated dozens of defenses from information just like that.”
A public defender with an accused murderer in 2014. Al Seib/Los Angeles Times via Getty
O’Toole mentions that the Supreme Court hasn’t always understood the importance of having separate hearings during the sentencing phase of capital trials. In his experience, the ability to explain the circumstances of his clients’ lives and upbringings has been critically important to whether or not they’re willing to put him to death.
If you haven’t “looked into the juror’s eyes when they see what a client has been through,” he says, you can’t understand just how important those hearings are to protecting the client’s rights against cruel and unusual punishment.
This is a fairly straightforward diversity argument: that it’s good for the Supreme Court to be able to draw on as broad a stream of personal experiences as possible. But the real asset that former defenders bring to the judiciary, defense lawyers believe, is that they’re used to seeing the law from the perspective of those they represent — and thinking in terms of its flaws.
That doesn’t just mean the pro-defendant viewpoint would be more strongly represented on the Court: Mere representation might still put a former defense attorney on the wrong side of a lot of 8-1 decisions. But lawyers are confident that having that viewpoint represented can help the other justices understand the principles at stake — even if they’re focused on the guilt or innocence of particular defendants instead.
The federal bench is getting more diverse — but the Supreme Court is still a glass ceiling
“President Obama has actually done a very good job of my view of trying to diversify the federal courts” with defenders “in a way that hasn’t really happened in my memory,” O’Toole says. “There are a lot more public defenders on the federal bench now than 10 to 15 years ago.”
When the Supreme Court rules on a criminal case, the composition of the lower courts matters a lot.
One example: a series of Supreme Court decisions that have restored some flexibility in sentencing to federal judges. In the past, Kaiser says, if something like that happened, the Supreme Court would “give some discretion to the lower courts, and they’d gum that rule to death.” But the lower courts have been “a lot more respectful” of this line of cases, “accepting the defendant-friendly implications.”
The impact has been enormous: From October 2014 to September 2015, slightly more than half of all federal sentences were shorter than the recommendations judges were afraid to stray from a decade ago.
But so far, that increase in former defense lawyers on the federal bench hasn’t worked its way up to the Supreme Court.

For many Democrats and progressives, the Gorsuch nomination has been painful because it’s a reminder of the thwarted nomination of Merrick Garland, who Barack Obama nominated in March 2016 but never got a confirmation hearing in the Senate.
But Garland himself was an ex-prosecutor, with a tough-on-crime record as a federal judge. The pain of the near-miss that Democrats feel with Gorsuch, defenders felt with Garland.
When Justice Antonin Scalia died, one judge on the shortlist to replace him — Jane Kelly of the Eighth Circuit — was a former public defender. Kelly had also been a victim of crime herself. In Kaiser’s words, she had “the best profile for a public defender candidate that you’re likely to see for the Supreme Court.” She was their best chance.
But Obama ultimately nominated Garland. Furthermore, reports in the days before the nomination suggested the president had deliberately taken Kelly off the Supreme Court shortlist, because he was worried that her experience representing violent criminals in court would make her overly controversial with Republicans. (Obama’s concern was obviously moot — Republicans didn’t move to confirm Garland, either.)
“John Adams defended the British troops who had fired in the Boston Massacre,” O’Toole points out. “But apparently that wasn’t as big a political liability then.” Even with emerging skepticism of tough-on-crime attitudes, though, today’s politicians are still too cautious to emulate the founders in this regard.
It’s a vicious cycle.
When former defenders are seen as too controversial to be nominated to the Supreme Court, young lawyers who might want to be Supreme Court justices one day get scared away from becoming defenders. When the Court doesn’t have anyone who can relate to defendants in criminal cases, it makes decisions that aren’t favorable to defendants.
When the Court restricts the constitutional rights of defendants, it gets harder for their lawyers to persuade lower-court and local judges and juries that their clients have rights, and that those rights are more important than the facts of what they did.
“Every important [criminal justice] decision came in the wake of somebody who did some pretty horrible things,” says Bhatt. Ernesto Miranda was charged with kidnapping, rape, and robbery. Clarence Gideon “was a robber, and a thief, and a card shark.”
But they still deserved the due process of law. That’s the principle that the Warren Court upheld, and that the current Court is at risk of hollowing out.

reprinted from VOX