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Wednesday, May 04, 2011

Supreme Court Advocates: "The Best There Ever Was"

Who is “the best there ever was” as an advocate before the Supreme Court? 

I’ve been thinking about this lately due to a couple of scheduled trips to the Supreme Court later this month.  When I posed the question on a con law listserv, the discussion immediately moved to one of criteria: How does one measure greatness as a Supreme Court advocate?  Does it involve eloquence?  Most wins?  Best performance on behalf of a worthy cause? Greatest skill in getting the Court to change its mind?

However difficult, it seems to me that the task of identifying excellence is worth pursuing, given that we are tasked with training lawyers who may someday find themselves arguing before the Supreme Court.

Obviously, there is no single measure of greatness.  Even “winning” is somewhat incomplete since part of a lawyer’s job would be to create a “soft landing” in a losing case by convincing the Court not to rule as heavily against your client as they might have done otherwise.

Perhaps, though, we could achieve some degree of consensus about “the best there ever was” by identifying an advocate who has the highest score across a range of categories:  Greatest number of wins, in cases involving a worthy cause, in a manner that appears to have moved the Court in a direction it was not previously disposed to move.

If that’s correct, then I am ready to nominate my choice for the best there ever was: Hayden C. Covington


Posted by Kurt Lash on May 4, 2011 at 09:17 AM | Permalink


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As for performance at oral argument, I put Paul Clement in a tier by himself, with an empty tier after him, and the next-best practioners starting a third tier. The third tier would be the first tier if Clement didn't exist. But he does and, at oral argument, is just better by an order that anyone else. In no particular order, the other current greats, such as Roberts, Waxman, Stewart, Phillips, Mahoney, Sullivan, Fisher, Bursch, and maybe ten or so others, would be distributed from there, though I'd put Roberts and Waxman at the top of the next-best tier. Waxman is fantastic at oral argument though we all recognize the knocks on him--shows of frustration and bravado, excessive stridency, his evident struggle to rein himself in, and the always-sense that he may just finally tell Scalia where to put it. My opinion takes into account S.Ct. advocates practicing today and stretches back only through Rehnquists's tenure as Chief Justice. Net net, I've never heard anyone argue in the Supreme Court as brilliantly--and as consistently brilliantly--as Clement.

Posted by: Jacjacjac | Jan 16, 2016 10:42:42 AM

Judicial bobble heads no longer seem to be in vogue. Perhaps it is time for SCOTUS appellate practice cards in the manner of baseball cards honoring all of the great appellate advocates going back to the beginnings of SCOTUS. Free market trading of cards would follow, with pricing eventually perhaps determining "The Best There Ever Was." Even the Justices might get involved with trading cards. And CJ Roberts could serve as the umpire.

Posted by: Shag from Brookline | May 7, 2011 5:08:42 AM

Norman, I disagree. I think we just have a basic disagreement on the extent to which legal argument is a contingent social practice. If you believe deep-down that I think you're right, I think you are mistaken.

Posted by: Orin Kerr | May 6, 2011 8:19:24 PM

In response to anon scotus fan and, I guess, Orin too, I don't think appellate advocacy has changed in ways that make cross-generational comparisons incoherent. We still teach and cite the cases from the nineteenth century, so the end-product of the advocacy -- the judicial decision -- has contemporary resonance. The substance of those decisions -- the rules and rationale for them -- are all based in sources of law that remain central to modern interpretation and therefore to modern, legal argumentation. Webster, like Roberts, consulted text, history, structure, precedent in forming his arguments to the Court. If we (or Justice Scalia) can grade Roberts' skill in argumentation, why can't we grade Websters'?

In that respect, I think the better analogy is to golfers: Bobby Jones did not have the benefit of carbon graphite shafts and super-tech golf balls; consequently, without the benefit of 300 yard drives, he had to play the golf course -- some of the same courses that the modern pros play -- differently (different club selections, different strategy). So, yes, the game has changed. Nevertheless, we can look at videos of Jones' golf swing and see features in it common to modern golfers' -- features that have a timeless elegance and beauty in them. As such, to say that Jones was a better golfer than your typical hack today -- or even to say that he was one of the best of all time -- is not to engage in some weighing of incommensurable qualities.

Finally, not to be snarky, deep down I believe all of you doubters believe the same with respect to legal argumentation. If Roberts had been forced to dispense with a written brief and present all of his arguments orally over the course of a couple of days, do you really think he would have been just average or worse? That he couldn't have adapted to the different style and form of argumentation? If so, our current Chief Justice owes his position not to any great intellectual fitness for office but to the ever-evolving Rules of the Supreme Court -- specifically, Rule 28 and 33 (limiting oral argument times and brief length, respectively).

Posted by: Norman Williams | May 6, 2011 1:00:14 PM

"Swan song" maybe not the best metaphor--acknowledged.

If you're not aware, there are plenty of of recorded oral arguments featuring Marshall in the 1960s.

From the Blackmun papers, Roberts was not graded as much of a stand-out in oral arguments (see 85 Wash. U. L. Rev. 457 (2007))...but I suppose you'd expect him to have more finely honed talents in the mid-1990s and early 2000s, which Justice Blackmun didn't witness.

Posted by: anonanana | May 6, 2011 11:47:43 AM

If you're looking for something instructive, try Kristina Swartz in Tolentino v. NY, 3/21/11. She stood her ground against unrelenting pressure and made her points and all she got for it was a DIG.

Posted by: r.friedman | May 6, 2011 11:15:21 AM

This might be the answer to Stuart's:

" ... but I don't know how many other Justices he thought agreed with him."

Probably 5-4.

But of course Scalia's view is hearsay at least once removed from Stuart.

As to anonanana's expression of shame that Davis' swan song in Brown was not recorded, was Thurgood Marshall's "victorious song" recorded? If not, that would really, really be a shame.

Posted by: Shag from Brookline | May 6, 2011 9:49:52 AM

Back in 2001-02, Scalia told a friend of mine that he and other Justices thought Roberts was far and away the best oral advocate, without even a close second. So I know that Scalia thought that, but I don't know how many other Justices he thought agreed with him.

Posted by: Stuart Buck | May 5, 2011 7:34:03 PM

On the cross-generational comparison: Yes, similar arguments are raised and accepted/rejected re baseball, music, etc. But some cross-comparisons are different. With music, different tools are available, and different styles are appreciated by audiences, but in the end, the broadest goal is to make something that sounds good to someone. With baseball or football, the rules and equipment may change, and it's a judgment call whether the changes have gone so far as to obliterate the fundamental commonality of hitting the ball, running the ball, etc.

But wherever we'd draw the line, I think we'd all stop shy of comparing a pitcher to a quarterback, under the common idea that they both throw balls.

So, in response to Orin's point and his interlocutors:

Maybe it is true that modern advocates, with a hot bench, can still be compared to advocates in the 1950s and 1960s, and that's similar to changes in baseball dynamics.

But when you get to Daniel Webster vs. John Roberts, they're not even doing the same thing. No cert., oral speech without a brief, etc. That, to me, is like comparing a pitcher and quarterback, so then it does break down.

Posted by: anon scotus fan | May 5, 2011 4:36:58 PM

For oral advocacy, many of the career deputy solicitor generals in the 1970s were more impressive to my ears than Robert Bork.

It's a shame the John W. Davis swan song in Brown v. Board of education wasn't recorded.

Posted by: anonanana | May 5, 2011 2:42:39 PM

CJ Rehnquist has been described as a mentor to John Roberts, who also clerked for him, which might suggest that Rehnquist had a "homer" bias in his selection. Query whether Roberts in his practice before the Supreme Court considered the Justices as umpires, and if so, whether Roberts did those things comparable to a baseball player to convince the umpire he was safe, did not swing, got hit by a pitch, etc?

Posted by: Shag from Brookline | May 5, 2011 8:45:25 AM

Also, Chief Justice Rehnquist apparently said that the best advocate practicing as of the mid-1990s was John Roberts.

Posted by: Orin Kerr | May 5, 2011 8:08:02 AM

Shag writes: "As to Orin's suggestion for gauging the best, I'm curious as to whether Justices would respond if asked. Have active, or retired, Justices commented on 'the best'?"

Yes, some have. In terms of statements made for a public audience, for example, I've heard Justice Stevens express the view that the best during his tenure was Robert Bork.

Posted by: Orin Kerr | May 5, 2011 8:03:19 AM

Query: What if Webster's lawyerly skills had prevailed in Charles River Bridge v. Warren Bridge regarding America's future? But for CJ Taney's replacement of Marshall, Webster might have prevailed. In evaluating Webster's skills as an attorney, might we consider his role as a Senator with the Fugitive Slave Act of 1850?

As to Orin's suggestion for gauging the best, I'm curious as to whether Justices would respond if asked. Have active, or retired, Justices commented on "the best"?

By the way, at VC Blog Orin takes a "shot" at the Brandeis Brief. His aim has been questioned.

Posted by: Shag from Brookline | May 5, 2011 6:48:54 AM

Orin, in the early nineteenth century, lawyers did not file written briefs beforehand; rather, the whole argument presented to the court consisted of the oral argument, which could (and in the big cases, did) run for days. The only detailed accounts we have of Webster and other early nineteenth century advocates' arguments are contained in the summary or report made at the beginning of the decision in the U.S. Reports, which summary was compiled by the court reporter (some of which were better than others). I like Webster's arguments in both Gibbons and McCulloch because he devoted most of his time to the "big picture" claims involving the nature of the union and what that implied for federal power (because he correctly understood more than the other counsel that the decisions would turn on these larger claims). In contrast, co-counsel in those cases typically devoted their time to more technical, legal arguments that Chief Justice Marshall would quickly dismiss or even ignore entirely in the ensuing opinion. It's that keen appreciation of what will move the court that distinguishes the great advocate from the good one in my view.

Posted by: Norman Williams | May 4, 2011 7:42:25 PM

In listening to many of the more recent recorded arguments, I'd say Seth Waxman really stands out.

In my opinion, John Roberts stands out more for his excellence in S. Ct. brief writing than his oral argumentation.

Posted by: anonanana | May 4, 2011 7:11:00 PM

Oh, and Norm, I agree re Paul Clement and Seth Waxman: They were two best I saw when I was a law clerk, although I don't think they were perceived as quite in Roberts territory. I don't think I saw Frey or Dellinger argue when I was there, though. Any of those names are certainly fine, though, if you're looking for examples of advocates to learn from.

As for Daniel Webster, can you point me to a brief he wrote that you think is the model you would give to a student today? If you can give me a link to the brief, I'll read it, and I'll let you know if I think it is still the best model to follow.

Posted by: Orin Kerr | May 4, 2011 7:06:48 PM


Your characterization of my argument had no connection to anything I had said, so there was no offense taken.

As for why I think John Roberts was so good, I don't know if you're unsure of what advocates do, or if you're asking me what in particular about Roberts' approach was so effective. But in my view, the goal of an advocate is to make the most of the legal materials available in crafting the most persuasive arguments that have the best chance of getting a majority of votes in favor of one's client. It's not a question of legal theory, but rather of optimizing your case for your client in light of the judges you have. John Roberts was generally recognized among the Justices, the law clerks, and fellow members of the bar as among the very best at that during his time in legal practice. In any event, if this strikes you as puzzling, or like something in a foreign language, I recommend Justice Scalia's book with Bryan Garner about appellate advocacy. It's excellent.

Posted by: Orin Kerr | May 4, 2011 6:51:46 PM

Orin, I agree with Kurt: why do you think that only contemporary advocates can serve as role models for current or future lawyers? There are obviously differences across time, but I tend to think that there are some timeless skills that all great advocates possess: Preparation, clarity, identifying which arguments are persuasive and which aren't, understanding the implications of your argument and being able to explain its limits, to name just a few. For that reason, I think a current student would learn much more by reading Webster's arguments than reading the brief of or listening to the oral argument made by a number of modern advocates.

FWIW, as a former member of a U.S. Supreme Court practice group before joining the academy, I witnessed many arguments by the current Supreme Court bar. John Roberts was an excellent advocate, but, not being able to call Webster or John Davis back to life, I'd pick Andrew Frey, Walter Dellinger, Seth Waxman, or Paul Clement over Roberts any day.

Posted by: Norman Williams | May 4, 2011 6:48:28 PM


Please forgive my accusation of silliness. I can see you're quite serious. But still, I'm not quite sure what it is about Webster's skills that you think would not translate to today's practice of Supreme Court advocacy. His use of contemporary rhetorical style? His use of language common in the opinions of the justices who would judge his client's case? His methods for preparing for oral argument? In what manner are any of these skills "socially contingent" (beyond simply knowing your audience)? Certainly his actual arguments seem to have been quite durable across time. The same is true for Hayden Covington (another person who, I am sure, would cause more than one person to "roll their eyes"--both today and when he argued).

You seem to be applying a standard of contemporary excellence of Supreme Court advocacy, but have not articulated that standard. You tell me John Roberts was "arguably the best of the last 30 years." What, exactly, is the nature of that argument?

Posted by: Kurt Lash | May 4, 2011 6:12:08 PM


If you're seeing this as just a fun parlor game, then my apologies for intruding on the fun. If you're trying to give advice to students, though, I think it's "rather silly" (in your words) to point students to advocates from the 18th or 19th century. Lawyering and advocacy have changed dramatically since then. An advocate who argued like Daniel Webster in today's U.S. Supreme Court would be laughed at and dismissed. Eyes would roll. You may have a theory of excellence by which you think you want to tell students to argue like that anyway. But I think it's based on a basic misunderstanding of the socially contingent nature of effective advocacy.

If you want to teach students about the standards of advocacy in appellate courts today, and if you're focused on oral advocacy, rather than written advocacy, you might go to oyez.org and play some of the oral arguments of John Roberts when he was in private practice. He was arguably the best of the last 30 years, and his approach is very instructive for those learning to give an effective argument.

Posted by: Orin Kerr | May 4, 2011 5:15:02 PM

Maybe not the all-time best but certainly noteworthy - staunch pro-Union James A. Garfield (then a congressman) argued for the petitioners in Ex parte Milligan. Also noteworthy because it was Garfield's first court appearance.

Posted by: Howard Katz | May 4, 2011 4:41:41 PM

Orin's point echoes similar arguments about comparing baseball players across eras: It can't be done, some claim, because pitching is different, or the ball parks are different, or the use of drugs is different, etc. Same thing for Presidents: They each faced a different set of historical circumstances, political realities, technological tools, etc. The same, of course, could be said for every human endeavor. Yet somehow, we continue to judge presidents, baseball players, architects, musicians, lawyers, politicians, religious leaders and representatives of every major human endeavor according to (disputed) standards of excellence.

And I think it is good that we do. It not only forces one to think about the set of skills required for successful participation in a given endeavor, it also forces one to confront the possibility that some celebrated figures warrant emulation while others do not. Orin's point about "luck" is true--which is why it's in my original post. But even this consideration helps one separate the truly gifted from the merely lucky. In fact, it is just this kind of analysis that can lead to a greater understanding of the skills that are important when luck runs out. This is why, even if a parlor game, the effort is not without some benefit. Legal practice before courts in the United States presumes the possibility of persuasive oral argument (pardon the alliteration). Certainly our students have a right to expect some instruction in standards of excellence in regard to oral advocacy. Is there really nothing to be learned from those who came before?

No doubt, one could get important insights by talking to current clerks and current members of the bar. But to say that we cannot make a judgment about the advocacy skills of Daniel Webster or Louis Brandeis without communicating with long-dead clerks and lawyers is, in my mind, rather silly.

Posted by: Kurt Lash | May 4, 2011 3:51:16 PM

Orin, why spoil such a fun parlor game? True, cross-generational comparisons are inherently dangerous, but, just as many declare President Lincoln to be the best President ever, there is fun and insight to be had in asking (and seeking to answer) who was the best among the Supreme Court advocates. The value in probing such issues is to make us confront precisely the issues you identify, as well as others.

FWIW, I think Orin unfairly dismisses the lawyers in the great cases as lucky bystanders. Admittedly, there's a chicken-and-egg problem lurking here: Were the cases great despite or because of the advocate's role? And, admittedly, there are plenty of times that the advocate likely played a peripheral role because the Court already knew what it wanted to say, but I think that is more true today, when the Court selects the cases it wishes to hear (and therefore has some initial idea as to outcome and rule). In the nineteenth century, the advocate played a more important part (as Orin seems to suggest), and, at least in some cases (such as Gibbons), there is good reason to think that the advocate shaped the Court's decision in a way that made the case great.

Posted by: Norman Williams | May 4, 2011 2:31:44 PM

off the top of my head, I'd nominate Louis Brandeis, too...

Posted by: Ian Bartrum | May 4, 2011 1:04:11 PM

The problem with the question is that there is no one Supreme Court: Because the personnel changes over time, as do court policies, there are effectively different Supreme Courts. Different advocates are going to be better or worse with those changes. For example, in the 1950s, there were very few questions at oral argument, so an attorney's performance at oral argument was mostly a lecture. In contrast, today's oral arguments are non-stop questions, with no lecturing beyond a 30-second introduction. It's a very different environment. Similarly, one of the major skills of a Supreme Court advocate today is writing a strong cert petition. But the cert process didn't arrive until the 1920s, so it's hard to know how to compare advocates from before that period.

As for measuring the best, if the goal is measuring the best lawyer *as a lawyer*, I don't think you should factor in the greatness of the cause or the significance of the opinion on the development of the law. Advocates don't write the opinions: The Justices do. So, for example, it sometimes happens that the reputations of lawyers as "great" are made in cases in which pretty much any lawyer with that case would have won, because the Justices were very likely going to rule that way no matter how good or bad the lawyering. In such instances, I don't think it's very sensible to say that the lawyer was the best. Rather, the lawyer was the luckiest, as he or she happened to have a major case that the Justices were already quite inclined to favor.

FWIW, I think the best way to gauge "the best" in a particular era is to ask the Justices, the outgoing lawclerks, and active Supreme Court advocates. And I don't think asking the "best" across different eras is such a useful question. My two cents, anyway.

Posted by: Orin Kerr | May 4, 2011 12:53:52 PM

I agree that Webster was a great advocate, but is it plausible to think that Webster moved the Court in a direction Marshall was not already predisposed (and fully capable) to move it?

Covington took over as lead counsel for the Jehovah's Witnesses immediately following their loss in Gobitis. He represented a socially despised group and sought enforcement of a right weakly protected (as a matter of precedent) before a New Deal court strongly disposed to defer to the political process. Even before his success in Barnette (which some attribute, unpersuasively in my mind, to the Court's revulsion at the post-Gobitis violence directed at Jehovah's Witnesses), Covington had successfully pressed claims on behalf of the JW's in Murdock and Opelika (II). In these cases, and particularly in his Barnette argument, he provided the Court a principled manner in which it could --and should--protect textualy enumerated rights like freedom of speech while still deferring to the political process when it came to economic regulation.

As Harlan Fisk Stone put it, "The Jehovah's Witnesses ought to have an endowment in view of the aid which they give in solving the legal problems of civil liberties."

Posted by: Kurt Lash | May 4, 2011 11:40:26 AM

Daniel Webster -- he had many victories but McCulloch and Gibbons were two huge ones. Those decisions have continuing resonance today in the battle over healthcare reform

Posted by: Norman Williams | May 4, 2011 11:01:05 AM

I would throw my vote to Daniel Webster. He argued 223 cases before the court including Dartmouth College v. Woodward, McCulloch v. Maryland and Gibbons v. Ogden. It is kind of hard to beat those cases for influence on the Constitution.

Posted by: Kevin Hill | May 4, 2011 11:00:04 AM

I was initially going to say Thurgood Marshall, but it seems more reasonable to say that his cases moved the Court in the direction it was already predisposed to move.

Kuty, what leads you to conclude Covington steered the Supreme Court in a new direction?

Posted by: Jake Linford | May 4, 2011 10:00:29 AM

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