Tariffs have been front page news since the 2024 presidential campaign. In February 2025 (and again in April 2025), President Donald Trump issued executive orders levying tariffs that threatened small and large businesses alike. But only one CEO of a small family business stepped forward…with only one major law firm.
In this episode, Rick Woldenberg, CEO of Learning Resources, Inc. and Hand2Mind, and his counsel, Pratik Shah, Head of the Supreme Court and Appellate Practice at Akin Gump tell the impossible story of how they overturned the Trump tariffs in less than a year.
Woldenberg and Shah met on Good Friday in April 2025 and by Tuesday after Easter weekend, filed a complaint in District Court challenging the tariffs, having never met each other in person. This is a story about how aligning on goals, committing to clear and honest feedback, and being engaged and open to other opinions can be rocket fuel for a successful client relationship (and result).
—
Listen to the podcast here
Speed Of Trust: How A CEO And His Lawyer Got A Supreme Court Win In 10 Months Rick Woldenberg, CEO Learning Resources, Inc. And Pratik Shah, Partner Akin Gump
I’m Rick Woldenberg, the CEO of Learning Resources and hand2mind, from Vernon Hills, Illinois. A fun fact about me is I went bungee jumping off the original bridge in New Zealand by choice.
My name is Pratik Shah. I’m Head of the Supreme court and Appellate Practice at Akin. A fun fact about me is I attended LeBron James’ rival high school in Akron, Ohio. I can’t claim to have ever played against him, but much like LeBron, I’m very proud to call Akron my hometown.
‐‐‐
On this episode of the show, I’m beyond thrilled to welcome Rick Woldenberg, CEO of Learning Resources and hand2mind, and his colleague and attorney, Pratik Shah, who is Head of the Supreme Court and Appellate Practice at Akin Gump. They’re going to take us on a pretty quick journey through the Supreme Court, where they successfully partnered to overturn the Trump tariffs.
‐‐‐
Rick, Pratik, I am so excited to have you. Thanks for being here.
Thanks for having us.
Rick, I owe this interview to a mutual friend of ours, Eric Seale, who’s the chair of my board and is a reader of the show. I’m very grateful to Eric for connecting us. We don’t usually cover Supreme Court cases on the show, but we’re going to go through this one for many reasons. First of all, we’re on the other side of the 4th of July and our nation’s 250th anniversary. I can’t think of a more relevant case for this moment in history where we’re re-establishing American values and our Founding Fathers’ values. Rick, tell us a little bit about the company, why this case got your attention, and why this was important.
Thanks for having me. Our business is a family business. This goes back to a business that we don’t have anymore. It was purchased by my grandfather in 1916. Part of the mindset is part of a business that’s over 100 years old and continuing. I’m third generation. I have kids in the business. They’re fourth generation. That infuses and affects your worldview.
Our business makes educational products and educational toys. We sell in over 100 countries. We have about 500 employees and full-time equivalents. You have a real sense in a business like that that’s mission-driven of the impact of what you do. If you put those two things together, I have a little mama bear in me that wants me to protect this enterprise for any number of reasons.
The Tariff Freight Train
The tariffs, which had been widely advertised by President Trump while he was on the stump, trying to win the election in ‘24, was a freight train coming our way, which we knew all about. We’d begun to prepare for it, but no one knew or expected what happened. It wasn’t what Mr. Trump talked about the stump. He talked about a maximum of 60%.
He was pretty gleeful in anticipation of Liberation Day on April 2nd, 2025, but wouldn’t tell anyone what was going to happen. I was in a meeting that day when I got out and saw what he did. I immediately killed the project to build a new building, closed down a potential joint venture in India, and began to focus on trying to survive. We’d been working on dealing with the fentanyl tariffs, which took us up to 20%, but between April 2nd and April 9th, 2025, our tariff rate went to 145%. I began to think, “What else could I sell?”
Building The Legal Dream Team
I had some experience in 2017, advocating against the border adjustment tax, which was a baby version of this. Due to that, I came into this dispute believing that this was illegal and unconstitutional. By April 7th, 2025, I decided that to survive all of this, I needed to amplify a communication strategy with litigation. I began to look for active litigation on April 7th, 2025. One thing led to another, and I washed up on Pratik Shah’s on April 16th, 2025, a week later.
To set the stage, the tariffs are announced in February 2025, and you all are in the Supreme Court in November 2025. I’ve been around litigation a long time, and that’s lightning speed. Pratik, I keep telling myself you almost had this case in the shoot. You were locked and loaded on this. Why were you ready?
Thank you, Stacy, for inviting me to join Rick to talk about our case. As Rick said, after President Trump was re-elected, it was no secret that the president planned new and aggressive tariff measures on an unprecedented scale. It was public knowledge that he wanted to proceed quickly, unilaterally, and without the limit’s substantive procedural and other limits in existing tariff statutes.
You don't need five arguments to win. You need one strong argument that the court can't ignore. Share on XAt the same time, my team here at Akin had been the only Supreme Court practice that had previously taken on a tariff challenge. We teamed up with our trade lawyers to challenge the China Section 301 tariffs from the first Trump administration. While the subject matter implicates trade law, this case that we thought was coming down the pike was ultimately going to be a challenge about separation of powers and executive authority. Those issues fall within my team’s wheelhouse as Supreme Court and appellate lawyers.
Given that backdrop, we had been retained early on by bigger business interests, even before inauguration, to explore potential avenues of a challenge to the likely tariffs, including potentially under IEEPA. We’d already been developing a legal theory behind the scenes, even before the president announced the first IEEPA tariffs in February 2025, and certainly before he escalated them dramatically on a global basis in April of that year.
While we had that legal theory, what we lacked was the right-paying plaintiff to sue. Given the administration’s track record of retaliation, there was no big business or industry group that was willing to pull the trigger on the suit. That’s where Rick and Learning Resources came in. I can let Rick tell the story of how he found me, and then I’m happy to talk about how we were able to get it to move along on your question about how we were able to get there so fast.
There are two things in my mind as you’re giving me the wind up here. First of all, I have a fire inside that a small business has to be the lead plaintiff here. Everybody was affected by these tariffs, such as giant companies, healthcare, and myself. Everybody was affected. We all owe Rick a great debt of gratitude for stepping forward. That is in my mind. Also, Rick, I want to hear about the timeline. You even describe it as speed dating about how you and Pratik connected. Tell us about that because it happened quite quickly.
I’m not 100% sure why I find myself sticking my neck out on these things as I do because I’ve done it before and I did it again not so long ago. It happens again and again. It may be a personal thing. On April 16th, 2025, I was told that I should call a guy named Pratik Shah, who I didn’t know was walking the earth. On April 17th, 2025, we met to talk about this case.
I was accompanied by my outside general counsel, David Brown, and my daughter, Alana, who was helping out on this project. James Tysse, Pratik’s partner, was on the call. They gave me a rundown of their strategy. There was no question. I was talking to the real deal, appellate, Supreme Court advocates, which is something I knew a little bit about from my background. I liked the strategy and the argument, so I was pretty much sold.
We had another meeting the next day when we began the process of mounting the effort to sue because it was certainly the case. I said in that meeting that this was all about speed, and I did not have time to wait. This was an emergency, and we needed to go. If they were willing to waste their holiday weekend for me, I was willing to pay.
Let’s talk about the holiday weekend. You said that you hired them on Good Friday.
The afternoon of Good Friday. We sued on Tuesday. It was an open weekend. No one was working. It was a holiday, so we could do this.
Plenty of time. Rick, originally, I thought I wanted to dive into how the CEO selects counsel. We didn’t go into this about your background, but you’re a lawyer and practiced law before you took over the family business. Pratik was tailor made for this, this case, so you didn’t do a lot of research. There wasn’t a lot of hand wringing about who to hire.
I’m a lawyer snob, so I think I know the difference. I worked at Mayer Brown, which also had a prominent Supreme Court practice. I was never a litigator. I never argued in court. I never stood in an appellate court in my life until this case. I was in a different part of the firm. I’ve litigated on behalf of the company, however. We have litigation experience as a client. In any event, having gone to the law school that I went to and hung out with people that I did, I felt confident that I could tell the difference.
When the government creates an existential threat to your business, you don't wait. You act. Share on XSince Pratik exceeded that standard by a wide margin, it wasn’t hard to tell I was in the right place. There’s also no question that it was a form of speed dating. He didn’t know who the heck I was. We had to quickly figure out how to work together successfully. I’ve worked with lots of lawyers, and I am a lawyer. I came into the relationship with some general ideas of how to form a successful partnership. I’ve been giving that a lot of thought over the years. We went to battle stations.
Let’s talk about that. There’s not a courtship, necessarily, that usually happens between lawyers and clients. You’re in it deep on a holiday weekend. Pratik, how do you figure out how to work together? Even though you’ve researched and you have a legal strategy, you still need a lot from Rick because he’s the facts. He’s the story of this case. How did you accomplish that over a holiday weekend?
In situations like this, you need a responsive client that’s engaged and knowledgeable. Rick checks all of those boxes and spades. Even better, it was one-stop shopping. Rick, while also the CEO who could speak authoritatively to the business, is also a former lawyer, which streamlined things a lot. This was not by committee. There weren’t eight different people to have to run things by. It was Rick on speed dial, and that helped things.
I learned quickly early on from our very first conversation that this was a real emergency for his business. Speed was going to be as important as putting forth the strongest merits arguments we could. During the course of the case, there were two big procedural vehicles that we were able to use in order to get to that speed objective. They were pivotal beyond simply filing the complaint as quickly as we could that Tuesday after Good Friday.
One second, though. We’ve circled around what Rick’s goals were. You’re aligned. You’re like, “We want to win. We’ve got to overturn these tariffs.” It’s an existential threat to Rick’s business and most businesses in America. How do you learn that speed? As you were, pre-gaming the case, had you already thought through the speed angle? I want to explore how that came about because, in my experience, you don’t usually get to the Supreme Court in seven months.
There are tools in the toolkit that you have in order to try to speed things up. It’s very rare to have a situation like this where things fall in place as well as they did and proceed along the lines that we were hoping, so that we could get speed all the way and get to the Supreme Court and a merits decision within ten months.
The Power Of Speed
Honestly, even though we’re a Supreme Court appellate practice, the one big change in Supreme Court appellate practice is the emergence of an emergency practice. That didn’t exist until the Supreme Court started this shadow docket and all of that stuff. That has become a big part of Supreme Court appellate practice. When you have big, statutory, regulatory, constitutional challenges, people can move fast because those cases often don’t need discovery.
The first tool we used was a motion for preliminary injunction. We file that immediately after the complaint, like the next day. Often, we write the PI motion first, which is what we did for Rick. We write the PI motion before the complaint, and then we copy and paste. What we want is the themes that we care about and a court will care about in ruling on a PI. The two big things on a PI is to give them your strongest legal argument and irreparable harm. Those are the two things we focused on.
We filed that PI. The harm piece was we put together a very strong declaration from Rick. We were working closely with him over that weekend and early that week to make sure that as a business owner and the CEO, we had the strongest harm story we could do. Those were the true existential threat he was facing and the supply chains he was actively changing. None of those things could simply be remedied by after the fact refunds. That was piece one.
Why We Ditched The Extra Arguments
Piece two was coming up with a simple, strong legal argument. We thought we had one, which was a pure legal argument that requires no facts and no discovery. That was that IEEPA simply doesn’t allow for tariffs at all. One mistake that lawyers often make is they make 10, 5, or even 3 arguments. In some contexts, that might be fine if you’re looking to preserve issues, or you’re in a big trial and you want to throw everything against the wall and see what sticks.
When you’re trying to design a case to get to the Supreme Court and win on a pure legal issue as fast as possible. You have to have the confidence to go with your best legal argument and not clog things up with 3, 4, or 5 alternative arguments, some of which could be fact-laid and which gives the government an easy way to try to slow things down. Those are the considerations.
That feels a little brave to me, though. It’s a very strong argument. I face this a lot with outside counsel that I manage. They want to leave some room for pivoting. I want to acknowledge that for both of you, it seems like a brave move.
There were other aspects to it as well that was consistent with that. For one thing, we decided day one, before we filed our complaint, that the goal was to win on the law and the Supreme Court. We started in the district court. A lot of times, people will switch lawyers when they get into the appellate practice to be speedy. We used the Supreme Court counsel from day one.
We proved that the rule of law still works in America. You just have to be willing to fight. Share on XWe also streamlined the issues. Since we decided that the legal win at the end was what we were after and nothing else mattered, we asked for a remedy limited only to us. This was something we discussed. It was an idea that came from Akin. It dramatically trimmed what was left to argue about. Even when we presented our best argument, we removed from the case a lot of things that could have slowed us down because they would have to be decided. We took them off the table. Since we took them off the table, there was nothing to argue about. We could focus on the one and only issue, which was the law. That had the effect of allowing our case to proceed as quickly as possible.
A lot of the other arguments that you can make in a case like this tend to be arguments that maybe a lower court would adopt, but here, we knew this case would ultimately be resolved one way or another by the Supreme Court. The Supreme Court isn’t into record-based, factual, intensive arguments. They want to address the big legal issues.
Stacey, you were saying that it’s often attention. In most cases, you’re not just going to make the pure legal argument and shed everything out. In the sort of cases that we often do, where we come in at the appeal stage, we’re trying to funnel the issues to the strongest issues that are going to be most receptive to an appellate court or ultimately the Supreme Court. That’s a different strategy call than you might have in other types of litigation.
I’m grounded in hearing this. Ultimately, you knew it was going to the Supreme Court, so you were tailoring the whole thing for that audience and to the overarching client goal, which is speed. Rick, you talked about the percentages, but you didn’t say how much the tariffs were costing your business.
When the tariffs went to 145% based on the run rate their 2025 budget would have forecast, the cost in ‘24 of $2.3 million would have gone to $100 million.
What’s your annual revenue at the company?
It’s not that much more, so that was not affordable, to say the least. The thing is that Mr. Trump was clear that it wasn’t a one-time fee. It was an annual fee. Companies like ours were rounding errors. They didn’t care if we lived or died. They wanted car plants and iPhones screwed together in this country, so they came up with one big brush to tar everyone with.
For companies like ours, they were indifferent. There was a lot of publicity about how Mr. Trump regarded the toy industry and how many pencils a kid could have. He is very dismissive of the concern of the little people. It is not appealing to me to go to the people that work here who have mortgages and retirement plans based on their expectation that we’ll pay them and say, “I don’t know why you care so much about your circumstances. We’re rounding errors. You should take one for the team so that it can be another car plant someplace.” That’s not a message I’m delivering. I don’t agree with that. It was even more motivating to be insulted in that way and to use that to fuel our determination to get this thing fixed.
You’re glued to the phone all that holiday weekend, getting the complaint and then the PI out the door, signing declaration, correcting. Knowing what that fervor is at trying to get filings out, but then the case goes on. It goes very quickly. You’ve got to be involved the whole time. When we talked in prep, you said that you spent time writing memos for Pratik. Talk about that.
This is more like me and the client that I am. In devising the relationship with Pratik, I told him that what he needs comes first for me. Nothing is a higher priority. Whatever I’m doing, which he should not concern himself with, I will drop it to give him what he wants. I also recognize from working with lawyers and having been a lawyer that lawyers feel a strong obligation to cater to their clients, whatever their strange habits are.
When I would send him off detailed memos, I knew I was creating an obligation form. I told him, “I’m writing these things because it’s the most efficient way to tell you what I think. It’s for your benefit. You can disregard them if you want. If there’s something in there you like, great. You don’t need to reply. I’m going to do this anyway.” That became the environment. Sometimes, he would come back and say, “I like points 4, 12, and 17.” Sometimes, he would not, and that was perfectly fine with me.
What I know is that they took me seriously and they listened, which is to say they considered my point of view. Every once in a while, I could make a shot on goal and get the puck in the net. It was always a surprise. I kept shooting pucks, and every once in a while, a couple got through. That was how our relationship worked, and that’s how it continues to this day.
Are you writing memos?
I still send him long emails full of my own legal theories. Every once in a while, he likes some of them.
Speed isn't just an advantage in business; it's a necessity in the courtroom. Share on XPratik, were you like, “We’re trying to get this out. Another memo from Rick. Somebody’s got to read this and tell me if it’s any good.”
Excel type, Stacy.
Rick was certainly unlike most appellate clients, but all in the best possible way. Often, as appellate lawyers, we’re brought into a case after it has already been litigated in the trial courts. There isn’t that same reason for continuous close interactions with your client, given the nature and pace of ordinary brief writing and appellate argument. As we’ve talked about, this wasn’t the typical case. We were there from day one. We were moving quickly. Rick was not only an eager and engaged participant, but an informed one, not only on his own business, but as a former lawyer.
I would get those amicus briefs. I didn’t need to use AI because I had Rick who would provide me summaries of amicus briefs before I even read them. We get dozens of amicus briefs from the Supreme Court, and I would, within 48 hours, get a memo that has pulled out the best lines from each one. As Rick said, he would share his thoughts, but ultimately, he was very clear.
He would defer to our judgment and make it clear that if we needed to make decisions and move fast, we had his proxy. That was a lot of trust that we had between us. Even though it was in a short time, we spent a lot of time collaborating, and that made a big difference. I’ll give you one concrete example. We had won very quickly in the District Court in DC, and that may have raised expectations.
On appeal in the DC Circuit, we got stuck on a slower schedule, certainly a slower schedule than we wanted. In the meanwhile, the parallel case that had been filed in the Court of International Trade, that one was moving much more quickly in the Federal Circuit. In fact, they had gotten a decision in the Federal Circuit before we even had arguments in the DC Circuit. I talked to Rick about using what’s a pretty rare maneuver called cert before judgment. Rick was fully on board.
Tell us what that is.
The Cert Before Judgment Strategy
Cert before judgment is this vehicle that allows you to skip the court of appeals and go directly to the Supreme Court. As a bit of context, our court was filed in the DDC. The other parallel challenge to the tariffs by Liberty Justice Center was filed in the Court of International Trade. We thought it was important to have the cases from both courts, and that’s for two reasons. One is it was unclear which court had jurisdiction. You wanted to make sure that both cases were in front of the Supreme Court so that the jurisdictional issue drops out. There’s no way that the government can dodge the decision.
You got your bets covered.
It doesn’t matter which court has jurisdiction if both of them are up in front of the court. It can decide the merits. Jurisdiction doesn’t matter because clearly, one of the cases has jurisdiction. That was very important to us to have our case up there together with the other case. The second one is our case, we had won on that categorical legal argument of no tariffs at all, whereas the other case in the CIT had won under a narrower rationale because of precedent there that some tariffs might be okay, but these went too far. We thought our argument was the one that the Supreme Court was more likely to buy, so we filed that cert before judgment petition.
What does the court base their ruling on that procedural maneuver?
You got to convince them. They don’t want to be in the business of granting cert before judgement.
Everyone will leapfrog.
They don’t like to skip courts of appeal. You have to show that this is a truly exceptional case where the circumstances warrant them moving at such a speed that warrants skipping the court of appeals. Here, we were able to make that case to them for two big reasons. One is the one I mentioned that they needed both cases to avoid any jurisdictional problem of resolving the lawfulness.
You made that argument to them.
We made that argument. That was point one. Point two was this is an existential threat, and we need resolution as soon as possible to get both cases up there together. They agreed with us, and the court granted the cert before judgment petition. We had our case and the CIT case. This was in September 2025. We got the grant in September and then briefed over the next six weeks. It was a highly expedited briefing.
The argument was scheduled for November 2025. That was a big part of it and having Rick’s support to do these things. These things cost money when you’re litigating in two courts at once. We were litigating in the DC Circuit and in the Supreme Court in parallel until we got this petition granted. He was supportive throughout.
It was do or die, so what can I say? That particular juncture filing that brief or that motion was another example of the dialogue between my side, the client side, and Akin, the lawyer side. It was an instance where it wasn’t abundantly clear that we could file because the other litigants didn’t want to come with us. We wanted to go together with the CIT plaintiffs. They wouldn’t come with us.
Why was that?
They felt like they would be at a better advantage if they went through the Federal Circuit appeal. I think that was a risky decision, but it was a decision they made. We couldn’t make it for them. To me, this is one of the places where I can point to and show the caliber of the representation I had. When they declined, I was told that we had to go through the appellate process. I asked the question, which I’m not sure was expected, which is, “Why do the other plaintiffs get to decide for me?”
I then sent Pratik a memo. What he reported to me is that they took a vote of the team. The team decided that they should go ahead, and we should file alone. The reason I held that event in my mind as special is that I’m an elf. I was a lawyer, but I retired from working for Mayer Brown in 1990, so old and cold, perhaps. This showed how active they were in listening and how open they were to ideas that didn’t come from them.
We didn't sue for glory. We sued to protect our employees, our families, and our future. Share on XThey listened to me, thought about it, and decided for themselves. It was abundantly clear from day one by my choice that Akin Gump was in charge. I was not in charge. They knew that, but I gave them feedback, and they considered it and decided to roll the dice with the idea. That’s how we got to be the named plaintiff, which I did not know or understand at the time. Since we filed first at the Supreme Court, we were the named plaintiff.
I want to talk about that, too. There’s so much here. Pratik, what’s on my mind is that it’s such a short period of time. You guys didn’t know each other before, and yet Rick is giving you an immense amount of trust. He said you had his proxy. It’s moving fast. I’m assuming that you have to have a big team working on this case. How do you teach the people on your team how important and precious client trust is?
We try to model that. It’s not a big team. We tend to do our appellate stuff pretty streamlined. It was four of us that litigated. We work closely together. It’s by design of our practice. We’re a small Supreme Court appellate practice that is ten lawyers big. It’s by design so that we can be hands-on on all our most important cases. It’s not an army of associates that goes through six layers before it gets to me.
We’re hands-on. We work closely together. It’s not very hierarchical. That shows in our ability. One, everyone got to meet Rick and know Rick. He got to meet the team because of that. Two, it leads to a better quality product. For us, that part of it wasn’t as big of a challenge, given how we’re structured and how we tend to do things.
That’s cool. We have to go through the procedural weeds here a little bit. Rick, when we talked before in prep, you talked about legacy being a part of this case for you, and that you wanted the case to be named after your company. Pratik, if you could help us. I don’t know if this was part of the design of how you were handling the case, or if it was divine intervention or dumb luck that it worked out that you accomplished this goal for Rick, too.
That was not the priority. The priority was winning the case. I think Rick would agree with that as well. We designed the case to win. It turns out, based on our timing and all that it happened to be because our cert before a judgment petition was filed first, that it was a Learning Resources case. Rick and his company is the ideal plaintiff for this case for a lot of reasons. The nature of his family business, a fifth generation American business that makes educational toys, is a great plaintiff. It ensured everyone’s benefit to have Learning Resources out in front of this.
Our objective wasn’t about the case caption. It was about winning the case because we knew the stakes were far beyond those for Learning Resources. Rick was our client and Learning Resources are our client, but we’re well aware that if we were successful, it would be a much broader win for American businesses, consumers, and the rule of law, more broadly.
It was not for glory. It wasn’t to impress my law school classmates who thought I wasn’t going to be the one to get into the constitutional law textbooks first. It was something that happened. I didn’t know it was going to happen. I was never reluctant. I was enthusiastic about having my name on the case. I wanted our name first because I had nothing to be embarrassed about. We were exercising our rights as citizens. I was proud of what we did, and I still am proud of what we did. It’s about winning the case that mattered. Nothing else mattered. To me at least, the interesting aspect of this is glory. There are lots of interesting issues, but that’s the least interesting to me.
Let’s get us to the courthouse steps here. Pratik, the cases are running in parallel, and ultimately, a jurisdictional issue made the VOS case primary. You have a relationship with the appellate council for VOS, those plaintiffs. There was not a tug of war, but another deciding task on who got to argue. Talk about the coin flip.
We have been coordinating closely with the plaintiffs in the CIT case. I have a longstanding relationship with the lawyer they hired at the appellate phase, Neal Katyal. We had collaborated and filed what you call a motion for divided oral argument at the Supreme Court. When you have two different cases that are being briefed and argued in the same session or similar issues, typically, the default is you get one advocate. We filed a divided argument motion because both of us are Supreme Court advocates. Both of us had our theory, and they had their theory plus alternative arguments that they were making. They had 3 or 4 alternative arguments.
Instead of the one shot, one kill approach.
Remember, their case came through the Court of International Trade, which had some adverse precedent that made adopting our primary legal theory much more difficult. They had these arguments. We filed a divided argument motion. Oregon was also part of their case. A bunch of blue states had filed as part of the VOS case in the court of international trade.
There were three advocates, myself, Neal, and the Oregon Solicitor General. We had filed a divided argument motion, agreed that I would argue first, then Neal, and then the Oregon SG. About two weeks before the argument, the Supreme Court issued an order and said, “We’re good with the Oregon arguing in front of the states. The states should have their own advocate. We want only one lawyer for the private businesses, Learning Resources and the VOS private businesses.”
The Coin Flip Stalemate
At this time, Neal and I were both doing moot courts. We were coordinating closely. Each set of clients wanted their lawyer to argue. Rick and Learning Resources wanted me to argue. His client wanted him to argue. It doesn’t happen often at the Supreme Court, but sometimes, you get stalemates, where you have to experience Supreme Court lawyers, both fully engaged, and the established method for resolving when you’ve gotten to an intractable dispute is to flip a coin.
That’s the established precedent.
Sometimes, when you have more experience, there’ll be a moot off or something like that, but we were about a week away from the argument at this point. No one was going to decide between the two of us, so it came down to flipping a coin. I lost the coin flip, which was a tough pill to swallow personally, given how much we’d invested in the case, but I also knew the important thing was winning the case.
I worked very closely with Neal to make sure he was in the best position to make the best arguments. We continue to believe that our legal theory, which the district court in our case had adopted, was there. We worked together. Neal made the argument and did a great job, and then ultimately, the court saw things our way. There were a lot of ups and downs in this case, but ultimately, we got to the right spot there.
The other thing I’ll mention is that it wasn’t a foregone conclusion that any big law firm would be litigating this case. You have to remember. This was back in April 2025 when the administration was very much targeting law firms through presidential executive orders for representations that he didn’t like. Many of my partners rely on relationships with the White House, including lobbying regulatory practices.
I didn’t want to compromise their practices or the firm, more broadly, but as a Supreme Court and constitutional litigator, this is a big part of what I do. I am representing clients against government overreach. If you can’t defend your clients and seek to uphold the rule of law, including principles central to our constitutional structure, then you should probably find another line of work.
I was fortunate and proud to have the support of my firm for taking on this engagement for Rick and Learning Resources. At the time, we were the only big firm that brought any of the tariff challenges. All of the other tariff challenges until we started winning were brought by either conservative causes and public interest groups like the Liberty Justice Center or by blue state attorney generals. It was an important piece to have us involved from the beginning to get our legal theory on the table and ultimately get us to a good spot.
Shoutout to Akin Gump.
We were the first to jump in the pool.
You both deserve enormous kudos for that. As somebody who is a consumer of legal service, I have to tell you that it has changed the way I view certain law firms. I understand the business considerations, but ultimately, I want to work with a firm that does the right thing. We’re turning around the bend here. I wanted to ask you all for some last reflections on what it was like to work together on this landmark case. Rick, do you want to start off?
It was my lucky day when I met Pratik and the Akin team. With my background, having worked at a firm with the Supreme court practice, I was aware enough of what went on over there, but also, I was very aware of who these people were. For me to have the opportunity to work with a team of this caliber was like a dream. It was super fun, and it was super fun in pursuit of something very important. It is bizarre that, in our lifetimes, anyone needed to defend what James Madison did.
To have the opportunity to do that or the responsibility made this a very high stakes mega important thing. I couldn’t have been any more fortunate than to have the partners that I had. For me, it was a delight. We were fighting for something that we had to win. From a personal standpoint, I learned about a new level of the meaning of the word commitment. I was fully 100% committed to overcome all obstacles. Nothing provided an out. We had to get to the finish line. We had to win. It was a great, life-changing experience.
Pratik?
From my perspective, the real heroes here are Rick and the other small business owners that were willing to stand up and sue. If they weren’t willing to stand up and sue, you don’t have the cases here. You don’t get the ruling from the Supreme Court. It was a privilege to be representing Rick and his company in this case at the Supreme Court.
Defending American Values
This case says a lot. We’re in a time where a lot of people are questioning, to some extent, the rule of law and all of these things. Our case shows that there is a real role for our courts and our constitution in this world. The Supreme Court justices are not just nine politicians in a row. This was a majority Supreme Court of six Republican appointees, and yet we got 6 out of the 9 votes to say this was an unlawful action by the president.
I’m not suggesting that this suddenly means the tide has turned and the Supreme Court is going to rule against the president in every case or anything like that, but it shows that it is more than politics. There is a role for people standing up and trying to seek to preserve their rights. It was a real privilege to be a part of that.
Last question. I have a little bit of a preview of Rick’s answer, so I’ll start with you, Pratik. I use music in my life to get excited or deal with hard things. Certainly, I remember writing to a Ninth Circuit argument while listening to a Jay-Z song. What’s your pump-up song?
My kids would make fun of me because my musical tastes are very much dated. If I had to pick something, I’d probably go back to Eye of the Tiger, which is dating myself.
You think about it again. I can’t tell you how many lawyers pick Eye of the Tiger. There are no cuss words.
It’s vintage. Rocky was probably the first movie in the early ‘80s that I saw in a theater. I still think of that as the ultimate pump-up song for the underdog.
The response to the Ohio State fight song, too.
I’m a proud Buckeye as well.
I generate my own caffeine. I wake up excited. I did not require extra stimulation in this case. It was stimulating enough. It was once in a lifetime. It was my only rodeo. Every day was an excitement. We were climbing a hill. We have to keep climbing. I didn’t need music in this case.
I can see that. Thank you both for being here. I appreciate it.
Thank you.
Important Links
About Rick Woldenberg
Rick Woldenberg is a chemical engineer, lawyer and CEO of Learning Resources, Inc. and Hand2Mind that design and manufacture educational products used around the world. He’s also the man whose tariff case went to the Supreme Court — a fight about rule of law that he didn’t expect to become his defining moment.
About Pratik Shah
