[caption id="attachment_16243" align="alignnone" width="620"] Cuba's then-president, Raul Castro, right, shakes hands with Russian President Vladimir Putin at Revolution Palace in Havana, Cuba, July 11, 2014. Photo: Ismael Francisco/Cubadebate via AP[/caption] An already long reel of U.S. government sanctions grew longer this week, when President Donald Trump announced new penalties on certain transactions involving the government of Venezuela. Add that to the push for new sanctions on Iran prompted by the American withdrawal from the 2015 nuclear deal and measures designed to punish oligarchs in Russia, and international trade attorneys who work on the subject are busier than ever. Dechert international trade chair Amanda DeBusk, who recently joined the firm from Hughes Hubbard & Reed, described an “avalanche of activity.” “It’s not just sanctions about one country, it’s about multiple countries, all coming at once,” she said. The Roster The first big recent blow fell on Russia, when the U.S. Department of the Treasury—through its Office of Foreign Assets Control—imposed sanctions in April on a series of Russian oligarchs, their related companies and certain senior governmental officials. Then came Trump's decision to pull out of the Iranian nuclear accord, which involved the reimposition of sanctions lifted in 2015 and the promise of new ones. In a speech Monday, U.S. Secretary of State Mike Pompeo vowed these sanctions would wind up being the "strongest in history" when fully in place. Also Monday, Trump announced new sanctions following the re-election of Venezuelan President Nicolás Maduros in a vote boycotted by the main opposition party. American entities are now barred from engaging in or financing transactions involving Venezuelan government debt or equity in government-owned entities. Growing Complexity For international trade attorneys, the rapidly changing state of affairs means that clients have a perpetually evolving set of questions. "You don’t know on any given day what the crisis du jour is," said Holland and Knight partner Jon Epstein. The complexity of the practice has also grown. Past rounds of economic sanctions imposed by the U.S. government was blunter, targeting entire countries with sweeping embargoes. Now, the trend is toward "smart sanctions"—selective penalties meant to put pressure on targeted groups. "Those are great because it doesn’t punish a whole country for a specific activity the leaders are taking part in, but it also makes it harder to comply," said Judith Lee, who co-chairs the international trade practice at Gibson, Dunn & Crutcher. One challenge is identifying to whom a given sanction actually applies, complicated by the 50 percent rule. If a sanctioned individual owns over 50 percent of a company, that entity is also subject to sanctions—a relationship that continues all the way down the list of subsidiaries. "For a country like Russia, trying to figure out how this rule applies when the ownership structure is not transparent at all—sometimes in fact it is well-hidden—is really hard for companies to navigate," DeBusk said. "That means increasing due diligence obligations to figure out how the 50 percent rule applies." There's no shortcut to businesses, guided by their lawyers, doing this work themselves. Regulators won't indicate which entities are in the clear and which aren't. That's symptomatic of a larger trend fueling uncertainty in the arena. "I think that with the regulatory agencies, the side of their house that is issuing changes to the sanctions is quite active, but the side of the house that is involved in interpreting them is trying to play catch up like the rest of us these days," said Akin Gump Strauss Hauer & Feld partner Jonathan Poling. Another new tactic, emerging in parallel to smart sanctions, is "secondary sanctions" applied in relation to Russia and Iran that target foreign businesses, rather than American entities. Even though these secondary sanctions have been part of the toolkit since the 1990s, they have been rarely imposed by the United States, and even less so in circumstances where they will cause a huge "hullabaloo," said Shearman & Sterling partner Philip Orlovsky. "There's never been a secondary sanction imposed on a major European oil company, but the threat of it in the past has been enough to chill those kind of business transactions," he said. Part of that threat functioned through cooperation with other foreign governments, but with Iran, the European Union remains committed to the nuclear accord. It has even considered taking measures to bar companies in the region from stopping business with Iran if the reason is complying with U.S. sanctions. "My personal view is that sanctions only work when they're multilateral," Orlovsky said. "It depends on the threat of enforcement and the willingness of foreign governments not to push back." Illustrating how quickly the state of play changes, the Treasury on Thursday named nine new entities subject to secondary sanctions for procuring parts for sanctioned Iranian airlines. But whether these measures, and others sure to come, will be effective, remains an open question. "My clients, they don't know how real or how credible the threat is," Orlovsky added. "With this administration, and the unpredictability of the administration, they do have to take it seriously." The frenetic pace of change can, in some circumstances, lead businesses and others to misjudge the import of breaking news. For Jeremy Zucker, international trade co-chair at Dechert, this week's Venezuela announcement offered a good example. "When you took a moment to look inside, it was actually more smoke than fire," he said. "Folks are inclined to expect more big changes and at times might misinterpret small news for big news. In this particular instance, there was less to see than they had feared." Navigating the Boom All of this noise and uncertainty adds up to a boom period for sanctions attorneys. "When you look around town," said Poling, who is based in Washington, "there was always some senior partner that started out in this practice at every firm—they were sort of solo practitioners. Occasionally there were two or so." "What you've seen even before the Trump administration is an explosion in the numbers," he added. "Complexity and enforcement has significantly ramped up, and clients take [sanctions] as more of a significant risk, more like anti-corruption measures." For Epstein, the present moment is "like taking a drink out of a fire hose." "Right now we're running flat out," he said. "As a matter of practice management, sometimes the question is: Do you write a formal memo, do you get on the phone, do you send an email? I've found myself saying, 'Take a look at our alert, and if you have any questions, call me.'" This fervid pace comes in an environment where trade lawyers of all stripes already have their hands full. Along with the prospect of increased tariffs on a range of goods and even a potential of a trade war, they are grappling with the Committee on Foreign Investment in the United States' growing vigilance over foreign purchases of domestic assets. "Throughout my career, I've noticed that some areas are busier than others. But since 9/11, the sanctions work has really predominated," said Gibson Dunn's Lee. "I keep thinking that it's going to slow down and slow down and it hasn’t." These days she's no longer expecting such a thaw, recognizing the ease which with the government turns to sanctions—unfettered from judicial review or other checks—to meet foreign policy goals. "The temptation to use the tool of sanctions to combat a number of things is irresistible," she said.