When the US Supreme Court ruled last month that sweeping tariffs imposed by President Donald Trump were unlawful, two Law School alumni found themselves at the center of the landmark decision—one as the business owner whose company challenged the tariffs, the other as a constitutional scholar helping argue the case before the Court.

In Learning Resources v. Trump and V.O.S. Selections v. United States, the Court ruled 6–3 that the president exceeded his authority by imposing sweeping tariffs under the International Emergency Economic Powers Act (IEEPA). The 1977 statute allows the executive branch to respond to national emergencies but does not explicitly authorize tariffs.

Two UChicago Law alumni played key roles in the case: Rick Woldenberg, ’86, CEO of the educational products company Learning Resources, and Michael McConnell, ’79, a professor of law at Stanford and a former judge on the US Court of Appeals for the Tenth Circuit. McConnell also previously served on the faculty at UChicago Law (1985-1996) before joining the federal bench.

Together, their efforts helped produce a decision holding that absent exceptional circumstances or a clear congressional delegation, the power to impose taxes and tariffs belongs to Congress—not the president.

And while the decision dealt a major blow to a signature policy of the Trump administration, neither alum was motivated by politics. For McConnell, a conservative legal scholar who was appointed to the bench by President George W. Bush, the important constitutional issues were the draw. For Woldenberg, “it was business, not politics.”

A Business Owner Steps Forward

The case for Woldenberg began not in a courtroom but in the day-to-day realities of running a family business. 

Northern Illinois-based Learning Resources, which manufactures educational toys and classroom materials, employs 500 people. Woldenberg joined the company in 1990, when, after graduating UChicago Law and four years of private practice, he opted to join the multigenerational business that his family had founded in 1916.

Like many consumer-goods companies, Learning Resources relies heavily on imported products and components. When the tariffs were announced, the financial consequences were immediate.

“Based on our 2025 budget, and the rates that prevailed at peak that week, I determined that on a run rate basis they were asking us to pay $100 million a year in taxes,” Woldenberg said.

Even after tariff rates shifted, the burden remained extraordinary.

“Our marginal tax rate, with IEEPA tariffs thrown into regular tariffs and duties, federal taxes and state taxes, was in excess of 100 cents on the dollar,” he said. “Make a dollar, pay more than a dollar in taxes—you’re not going to stay in business for long.”

Initially, Woldenberg searched for existing litigation he could support. But when other plaintiffs withdrew from a planned lawsuit, the case suddenly lacked anyone willing to challenge the tariffs.

Rather than step aside, he moved forward himself.

“So, I’m not part of a group,” he said. “I am the group.”

The decision was driven partly by economics—but also by responsibility.

“Hundreds of families living in the Chicago area depend on our family enterprise for their livelihood,” he said.

Facing that reality, Woldenberg felt compelled to act.

“You don’t know in your lifetime when you’re going to be called upon,” he said. “I felt as if my values were being tested… I felt that I would be better off taking the risk than not.”

A Constitutional Question

While Woldenberg entered the litigation as a business leader confronting an existential financial threat, McConnell came to the case from the world of constitutional law—as a scholar, former federal judge, and veteran Supreme Court advocate.

McConnell, who is faculty director Stanford Law’s Constitutional Law Center, initially became involved by helping to draft an amicus brief analyzing the constitutional issues raised by the tariffs. At the center of the dispute was a fundamental question: whether the president could rely on emergency powers to impose sweeping tariffs without explicit authorization from Congress.

“The core issue was the scope of presidential authority,” McConnell said. “The administration relied on a statute that arguably gave the president extremely broad authority to impose economic sanctions in response to international crises.”

But the Constitution assigns tariff authority to Congress.

“So, the question was whether Congress had actually delegated authority in the way the administration claimed,” he said. “That raises a classic separation-of-powers question.”

McConnell later joined the legal team representing businesses in the V.O.S. Selections litigation challenging the tariffs, serving as counsel of record. When the case reached the Supreme Court, former Acting Solicitor General Neal Katyal argued on behalf of the private plaintiffs.

The two cases—Learning Resources and V.O.S. Selections—were consolidated for argument before the Court. The primary difference between them was procedural: the Learning Resources case originated in federal district court, while the V.O.S. Selections case began in the US Court of International Trade.

“It was a collaborative effort,” McConnell said.

Watching the argument unfold was striking after months of preparation, he added.

“You’ve spent months thinking about the issues, writing briefs, and discussing the case with the team. Then suddenly everything is condensed into a short argument in front of the Court.”

It is a feeling that never gets old for McConnell, who argued his first case before the Supreme Court as an assistant solicitor general when he was 28 years old.

Defending the Structure of Government

Although the case had major economic implications, both alumni emphasized the constitutional stakes.

Woldenberg framed the dispute in historical terms. “The Boston Tea Party was a tariff dispute,” he said. “The Constitution reflected that history by placing taxing authority in Congress. In representative government, a single individual cannot impose a tax on Americans.”

McConnell expressed a similar view.

“If Congress wants to give the president broad authority in a particular area, it needs to say so clearly,” he said. “The Constitution places the power over tariffs and trade policy in Congress.”

He also viewed the decision as reinforcing principles articulated in the landmark separation-of-powers case Youngstown Sheet & Tube Co. v. Sawyer, the Supreme Court’s 1952 steel-seizure ruling limiting presidential authority during the Truman administration. The case has long been a staple of constitutional law courses.

A Case for the Classroom

Like Youngstown, the Court’s decision in Learning Resources is likely to become a part of discussions and debate in constitutional law classrooms for generations to come, raising questions about presidential power, statutory interpretation, and the separation of powers.

So, while McConnell and Woldenberg arrived at the case from very different starting points—one from the factory floor of a family business, the other from the rarified world of constitutional scholarship—these two alumni’s divergent efforts converged in a decision that helps define the limits of presidential authority.

McConnell’s involvement in the blockbuster Supreme Court case seems the natural progression of a career path that began early on with a clerkship for Justice William J. Brennan Jr. 

For Woldenberg, whose journey into Supreme Court history was far less predictable than McConnell’s, the experience of seeing his family business’s name attached to a landmark Supreme Court decision is deeply personal.

“Ask any University of Chicago Law School grad how they would feel with their name on seminal litigation that's going to be in Elements of the Law for the rest of their life,” he said. “I can't really think of anything that would be more thrilling.”

Then he added with a laugh:

“I prefer this over winning the Powerball.”