What’s It Take To Argue a SCOTUS Case? A Lot Of Midnight Oil


When the chance to argue a case before the U.S. Supreme Court comes up, sleep becomes a distant memory. We got a behind-the-case look from some NCBA members who were there this spring. Find this story and more in the August edition of North Carolina Lawyer magazine.

By Amber Nimocks

Drew Erteschik’s phone buzzed in his pocket like a bug zapper. He first thought the texts were from his wife, suggesting what he might pick up for dinner. But one glance at the text from his law partner, “We have it!! We have cert!!” — the first of approximately 250 messages blowing up his phone — and he knew this was bigger than what was for supper.

It was Jan. 11, and the U.S. Supreme Court had just granted certiorari in N.C. Department of Revenue v. The Kimberley Rice Kaestner 1992 Family Trust. N.C. Solicitor General Matt Sawchak, Sawchak’s colleagues Jim Doggett and Ryan Park, former N.C. Supreme Court Justice Bob Orr, and Erteschik represented the Department of Revenue.

With the cert grant, the clock began ticking. The team had only three months to ready their A games for scrutiny by the U.S. Supreme Court. Sleep would be become a rare luxury for those focused on the case, as comprehensive research and analysis, brief writing, and argument preparation consumed all hours of the day.

“To prepare for that kind of experience, including the briefing involved, that’s five, six people or more, working pretty much wall-to-wall over a three-month period, culminating in the argument before the U.S. Supreme Court,” Sawchak said. “It’s like a ride on a rocket sled.”

Matt Sawchak

Drew Erteschik

At the heart of the case was the question of whether the Due Process Clause prohibits states from taxing trusts based on where beneficiaries reside. At stake were billions of dollars in tax revenue for the states, and the potential to shape constitutional law that the U.S. Supreme Court had not addressed in many decades.
As the Department’s team of attorneys wrote on the first page of their cert petition:

Eleven states, including North Carolina, tax trust income when a trust’s beneficiaries are state residents. For the last 90 years this Court has been silent on whether these taxes comport with due process. The Court’s last words on the subject come from the Pennoyer era of due-process analysis. Pennoyer v. Neff, 95 U.S. 714 (1878). As a result, lower courts and state taxing authorities have been searching in vain for modern guidance.
There is now a direct split spanning nine states. Four state courts have held that the Due Process Clause allows states to tax trusts based on trust beneficiaries’ in-state residency. Five state courts, including two state supreme courts this year, have concluded that the Due Process Clause forbids those taxes . . .
The Due Process Clause should not have different mean-ings in different states — particularly when billions of dollars of state-tax revenue hang in the balance.

Because Kaestner was one of the last cases the Court calendared for the term that ended in June, the timeline was particularly intense. The cert grant came on Jan. 11. Oral argument was scheduled for April 16.

“We were obviously very pleased about the cert grant, but it came late in the term, and we knew that our case would be set for one of the final weeks of argument for that term. That timing ultimately compressed the already tight briefing deadlines,” Erteschik said.

The Department’s opening brief was due Feb. 22. (Erteschik’s wife was due to have their second daughter on Feb. 23, a deadline not imposed by the Court; baby Audrey was born on Feb. 27.) On March 1, briefs of amici supporting the Department were due. March 18, the Trust’s response brief was due, and March 25 amici briefs supporting the Trust were due. The Department’s reply brief was due April 9, but they filed about half a week early.

Sawchak and Erteschik recounted the experience of petitioning for cert, briefing the merits, and preparing and arguing before the U.S. Supreme Court at a Lunch n’ Learn program sponsored by the NCBA Appellate Practice Section in mid-June.

Eight Is Better Than 18

Sawchak, who had been at counsel table before the U.S. Supreme Court in N.C. State Board of Dental Examiners v. Federal Trade Commission, presented oral arguments in the Kaestner case. His experience in the Dental Examiners case had whetted his appetite for appearing before the U.S. Supreme Court. Working on the Kaestner case put a wide array of his skills to use.

“Arguing in the U.S. Supreme Court involves unusually broad and intense questioning,” Sawchak said. “The Kaestner case doubled that analytical load. The case involves a number of different subject areas intersecting — and in a setting where there hasn’t been recent case law from the Supreme Court. All of those factors increased the challenge level in this case.”

Former N.C. Supreme Court Justice Bob Orr

Jim Doggett

Ryan Park

One relatively unique aspect of Supreme Court litigation, Sawchak said, is the number of amici curiae and how intensely they get involved. One of the most memorable moments of the case came for him on the Monday when the amicus briefs supporting the Trust were due. You don’t how many amici there will be, and the petitioner’s only opportunity to respond to those briefs is in a single reply brief, which is limited to 6,000 words. Between March 25 and April 9, the team would have to assess amicus briefs for the other side, formulate responses, compose a 6,000-word reply brief, and, as Sawchak said, “hopefully make it sing.”

On that Monday, he was returning from visiting his mother in rural upstate New York. Awaiting his flight in the one-gate airport, he watched his phone ping as the eight electronic amicus brief files landed.

“That was the most memorable airport experience I’ve ever had — reading all those opposing amicus briefs while waiting for my flight. It gets seared in your memory when you do intense work in an unusual place. That day was pretty intense,” Sawchak said. “The briefs can come in at any time until midnight, so I remember saying a prayer of thanks at 12:02 a.m. that it was eight briefs and not 18.”

Once the briefs were written and filed, Sawchak worked to get his oral argument ready. That involved two informal moot courts and two formal moot courts, one administered by the National Association of Attorneys General and the other by the Georgetown Law Supreme Court Institute. Sawchak crystallized the key ideas he wanted to express into a single two-column outline he referred to as a “cheat sheet,” which he memorized.

“You have to think critically and widely about what questions might come up, what major themes you hope to establish, and how to try to pivot from the Justices’ questions to try to re-anchor to your themes,” he said.

The night before oral arguments, Sawchak stayed alone in his hotel room, re-reading early 20th-century cases. For dinner, he grabbed a Subway sandwich in the Union Station food hall. The Subway soda was flat, so he finished his pre-argument gourmet dinner with a Diet Coke from a Walgreens. Back in his room, he watched the Hurricanes-Capitals hockey game to take his mind off the case.

The Argument You Relive

On the morning of the argument, the monumental nature of the day came into focus as the attorneys approached crowds lined up outside the Court.

“Your first view of the Court that morning, as you walk toward it, is awe-inspiring,” Erteschik said. “As you turn the corner onto First Street, and you see what looks like a mile-long line of people who have been lined up since the early morning hours, the experience becomes very real in that moment.”

Passing through the crowd, they talked with Tom Myrick of Moore & Van Allen’s Charlotte office, who was part of the legal team representing the Kaestner Trust, as well as with former N.C. Supreme Court Justice Barbara Jackson, who authored the N.C. Supreme Court decision they were challenging. They also recognized a number of other lawyers from North Carolina who were there to see the argument.

After waiting in the lawyers’ room, where storied generations of attorneys have fought last-minute jitters, Sawchak, Erteschik, Orr, and Deputy N.C. Solicitor General Jim Doggett settled into their seats at counsel table.

Orr and Erteschik at the U.S. Supreme Court.

What you don’t realize if you’ve never been there before, Erteschik said, is that the U.S. Supreme Court courtroom is really, really crowded.

“For reasons that make good sense, a very large number of people are allowed into the courtroom for the arguments,” he said. “It feels almost like the crowd is on top of you.”
Another thing that comes as a surprise: The counsel table is quite close to the bench.

“The spacing in the courtroom is uniquely intimate,” Erteschik said. “I felt as though I was an arm’s length away from Justice Ruth Bader Ginsburg. When you take your seat at counsel table, you realize that you are literally a few feet away from your heroes.”

Sawchak recalled that the short distance between the bench and the counsel table, combined with the curve of the bench, makes it impossible to make eye contact with every Justice during a response to a given question.

“Your peripheral vision fails you because of the short gap and the wide view,” Sawchak said.

What surprised no one was that it’s quite a challenge to get a word in edgewise when arguing before the Supreme Court.

“The questioning was so intense throughout my opening 27 minutes that the Chief Justice actually gave me extra time for re-buttal to get two syllables together,” Sawchak said.

When a colleague at the Lunch n’ Learn asked if he would’ve done anything differently, Sawchak paraphrased a famous quip from Justice Robert Jackson: “Every argument is actually three arguments: The argument you planned to give, the argument you gave, and the better argument you imagine in your fevered dreams the next night,” Sawchak said. “When you review the transcript, and you see situations where you could say only eight words before the next question came, you think, ‘Could I have chosen those eight words better?’ That’s where reflection for the next time comes in. But I leave this experience with a real hunger to do it again.”

Sawchak and his family at the U.S. Supreme Court.

When the argument was over, Sawchak had lunch with his wife and adult son and daughter. It was the first time his whole family had ever seen him in a courtroom.

On June 21, the U.S. Supreme Court unanimously affirmed the N.C. Supreme Court’s decision in N.C. Department of Revenue v. The Kimberley Rice Kaestner 1992 Family Trust.

“Although the result was not the one we sought, the Court’s opinion was a lot friendlier to states’ interests than it could have been,” said Sawchak.

Erteschik agreed. He said that he was quick to congratulate opposing counsel on the result, but at the same time, he was pleased with the decision’s broader implications.

“The Court replaced the state supreme court’s analysis with a new, flexible constitutional analysis. That flexible analysis will preserve significant tax revenue for our state — revenue that would otherwise have been lost if the state supreme court’s decision had remained as the last word.”

A copy of the Court’s opinion can be found online at: tinyurl.com/NCL-SCOTUS