Woldenberg joined Learning Resources in 1990 and became its chief executive eight years later. Since 2019, he has also been running hand2mind. The companies’ products are designed in Vernon Hills and Torrance, California, where they have another office, but virtually all of the items are manufactured in Asia, principally in China. Some of them enter through O’Hare, but most are shipped to ports on the West Coast, and then delivered by rail to the Illinois warehouse or sent to customers. These days, distributors include Scholastic, Walmart, and Amazon. In the early years, the Woldenbergs made some of their toys and learning aids at factories in the United States. But, in the eighties and early nineties, they moved almost all of their production to factories in China and Taiwan, where assembly-line workers earned a fraction of what their American counterparts did. “Everyone was finding lower-cost manufacturers overseas to build their products, and U.S. manufacturers couldn’t match them,” Woldenberg told me a few weeks ago, over coffee at the O’Hare Hilton. “We were in the most competitive consumer market in the world, and I didn’t think we had a choice.” He said that moving production offshore had enabled the business to hire more people in the United States, including product designers, salespeople, administrative staff, and warehouse workers. “I don’t feel guilty about what we have done,” he said. “We have created more than five hundred well-paying jobs, and our products sell in more than a hundred countries.” (According to Circana, a market-research firm, Learning Resources is the twenty-fifth-largest toy company in the U.S.) On April 2nd, which Donald Trump termed “Liberation Day,” the President announced blanket tariffs that raised the levy on Chinese imports to a hundred and forty-five per cent, upending Woldenberg’s business model—and many like it. Tariffs are essentially taxes, and importers have a choice of absorbing the cost themselves or passing it on to consumers, in the form of higher prices. Woldenberg said he quickly calculated that paying the new levies would wipe out his firms’ profits. About a week before I met with him, the White House announced that tariffs on Chinese goods would be reduced for ninety days, to thirty per cent, while negotiations between the two countries took place. Woldenberg welcomed this news, but, in a business where manufacturing orders have to be placed months before the goods arrive on U.S. shores, it did little to relieve the uncertainty and chaos that Trump’s tariff policies have created. “How am I supposed to make a business plan under these circumstances?” Woldenberg said. “I don’t even know what my costs are going to be. I’m living in a reality-television show, not reality.” Woldenberg’s first response to the Liberation Day tariffs was to pause his plans to build a new warehouse. His second response was to sue Trump and the Administration. On April 22nd, lawyers acting for Learning Resources and hand2mind filed a lawsuit in federal court, in Washington, D.C., which labelled Trump’s tariffs “an extraordinary Executive Branch power grab” that was “irreparably harming” the two businesses. Under the Constitution, the suit said, Trump didn’t have the legal authority to levy these tariffs without obtaining the approval of Congress. It asked the court to prevent the government from collecting tariffs from the Woldenberg businesses. The suit also demanded damages. The case was filed at a moment when major toy corporations, like Hasbro and Mattel, were standing pat, seemingly wary of confronting the White House. But Woldenberg, who holds a J.D. from the University of Chicago Law School and who worked at a corporate law firm before joining the family business, has been down this road before. In 2017, during Trump’s first term, he helped lead the toy industry’s opposition to a proposal for a “border-adjustment tax”—a kind of tariff—that Republicans, under pressure from the Administration, were thinking about including in their big tax-cutting bill. (The proposal didn’t make it into the final legislation.) Now that Trump has sidestepped Congress and claimed the right to impose tariffs at will, Woldenberg is taking on the White House directly. “In the past, I’ve supported both parties, and I don’t think of myself as a political person,” he said, in explaining the decision to sue. “But I will defend our mission, and I’ll defend our employees. This is a legacy business, and I feel a certain responsibility for it. I won’t let Mr. Trump take it away from us.” There are trade statutes that empower the President to levy tariffs in specific cases, such as when a foreign country has been engaging in unfair trade practices. But these laws don’t cover blanket tariffs of the sort Trump introduced on April 2nd. The Administration, in announcing the levies, instead cited a different statute, the International Emergency Economic Powers Act (I.E.E.P.A.) of 1977, which previous Presidents have used to freeze foreign assets during national-security crises. At a court hearing in Washington a couple of weeks ago, lawyers for the Justice Department argued that Trump’s tariffs were a national-security issue and that a decision against the Administration would “kneecap the President on the world stage, cripple his ability to negotiate trade deals and imperil the government’s ability to respond to . . . future national emergencies.” (The government also asked the court to transfer the case to another venue, the federal Court of International Trade, in Manhattan, where trade-related cases are often heard.) In a ruling on May 29th, Judge Rudolph Contreras rejected the Administration’s arguments and issued an injunction preventing the government from collecting import duties from Learning Hands and hand2mind. “This case is not about tariffs qua tariffs,” Contreras wrote. “It is about whether IEEPA enables the President to unilaterally impose, revoke, pause, reinstate, and adjust tariffs to reorder the global economy. The Court agrees with Plaintiffs that it does not.” On the face of things, this ruling handed a momentous win to Woldenberg, who attended the hearing with his wife and three grown children, all of whom work for the business. Judge Contreras’s decision came just one day after a federal court had struck down some of Trump’s Liberation Day tariffs. On May 28th, a panel of three judges hearing two separate cases before the Court of International Trade had ruled that the April 2nd tariffs “exceed any authority granted to the President by IEEPA.” These cases were brought, respectively, by five small businesses supported by a libertarian legal group, and by a posse of Democratic state attorneys general. The adverse rulings in the two courts were a major legal setback for the White House. It’s still far from clear, though, whether they will lead to any major changes in Trump’s tariff policies—or to lasting relief from its provisions for Woldenberg’s businesses and others in similar predicaments. Judge Contreras initially delayed enforcement of his order for fourteen days, to give the Administration time to appeal, and last week he suspended the injunction while that process works its way through the D.C. Circuit Court of Appeals. Meanwhile, the Court of International Trade order blocking Trump’s tariffs had already been put on hold. A day after the verdict, the U.S. Court of Appeals for the Federal Circuit stayed it, pending further legal arguments. At least for now, then, Trump’s Liberation Day tariffs remain in effect. So do the other levies he has imposed, including duties of twenty-five per cent on automobiles and auto parts, and of fifty per cent on steel and aluminum. There is talk of him imposing hefty new duties on other goods, including pharmaceuticals and commercial aircraft. To preserve its blanket tariffs, the Administration has said that it is considering various legal options, which could conceivably include evoking the notorious Smoot-Hawley Tariff Act of 1930, a piece of legislation that some economic historians blame for deepening the Great Depression. Under one of that statute’s provisions, Trump could theoretically impose tariffs of up to fifty per cent on items from any country that he judged to be placing U.S. goods at a disadvantage. Last week, Commerce Secretary Howard Lutnick declared, “Rest assured, tariffs are not going away.” Woldenberg’s initial reaction to the initial ruling from Judge Contreras was one of delight. “I had not allowed myself to dream about such a victory,” he told me over the phone, last week. But his celebrations were muted by the fact that the tariffs his companies are facing remain in place pending the Administration’s appeal. “The rulings have not changed anything in our business,” he said. Right now, he is rushing to get shipments from China through U.S. customs by August 12th, when the ninety-day reduction in Trump’s Liberation Day tariffs are set to expire. After that, Woldenberg said, things are up in the air. A small but significant part of Woldenberg’s business involves selling goods that are shielded from the tariffs, such as educational texts. This will continue as normal, he said. He has also taken a gamble and ordered some items that are subject to tariffs, even though he won’t be able to turn a profit on them if the rate reverts to a hundred and forty-five per cent. Looking further ahead, he is exploring the possibility of shifting orders to factories in Vietnam and India, which may end up being subject to lower tariffs than Chinese plants—although it still isn’t clear exactly what tariffs those countries will face. I asked Woldenberg if his companies could move some production to the United States. He said that wasn’t a practical option. U.S. factories simply don’t have the capacity to make the goods his firm wants at the quality it demands for competitive prices, he insisted. For now, the Trump tariffs that remain in place are raising costs for Woldenberg’s companies, and both have started to raise their prices. “I don’t like doing that, but it is a force-majeure situation,” he said. “We have to find a way to finance paying these taxes. There is no escaping that.” As Woldenberg’s lawsuit heads to the appeals court, his legal bills are also mounting. His lawyers, who include a team from Akin, Gump, Strauss, Hauer & Feld, an élite corporate law firm, don’t come cheap. Woldenberg acknowledged he had received some outside support from others who want to see the tariffs lifted, but, he said, “they are not exactly lining up at the door.” He added, “I am not involved with any political groups. I will not accept money from politically oriented people.” When I first spoke with Woldenberg, he predicted that at least one of the tariffs cases would ultimately go to the Supreme Court, and he said that the Justices would have a momentous decision to make: “It is a case of whether we are a monarchy.” In our conversation last week, he said he was assuming that the federal appeals courts would decide in the next few weeks whether the Liberation Day tariffs on his companies would remain in place pending a resolution of the case; he thinks a final verdict could take another six to nine months. The litigation and the media coverage surrounding it have largely taken over his life. In recent weeks, he has appeared on CBS News, CNN, CNBC, and MSNBC, as well as on local channels in Chicago. His newfound prominence potentially places him and his family’s business in the firing line of the Trump Administration—an uncomfortable position for anyone to occupy—but he still seems very much up for the fight. “All in, all the way,” he said. ♦