Law Firms: Don't Expect 'Quiet' Sanctions Year
Companies should expect the Trump administration to continue to rely heavily on sanctions and sanctions enforcement as a foreign policy tool in 2026, including through new designations to pressure countries in the Western Hemisphere and penalties on gatekeepers that enable evasion, law firms said this month. They also said it's still unclear how the U.S. will approach its sanctions regime against Venezuela, although the administration would likely be able to easily roll back many of those restrictions.
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Holland & Knight predicted that 2026 will be an even more active year for sanctions, especially as President Donald Trump embraces an aggressive foreign policy approach that combines sanctions, tariffs and the increasing use of military force.
The firm specifically said the U.S. could use sanctions more frequently if the Supreme Court rules that the International Emergency Economic Powers Act doesn’t allow for Trump’s sweeping tariffs. If that’s the case, “U.S. sanctions will be forced to carry even more weight in the months ahead,” it said in a client alert.
“Those expecting a quiet year in sanctions should think again,” the law firm said, adding that companies should prepare by reviewing red flags for sanctions evasion, evaluating their risks and considering updates to their compliance policies.
Holland & Knight said it's expecting the government to continue to use its sanctions authorities in the Western Hemisphere, especially after the military’s capture of Nicolas Maduro earlier this month. It noted that the U.S. has since threatened the leaders of Colombia and Cuba with “similar fates.”
“In 2026, the U.S. will continue to rely on counterterrorism and counternarcotics sanctions to advance its security interests in the region -- efforts that are now reinforced by the threat of kinetic action,” the firm said. The U.S. already has sanctioned a range of cartels and other criminal organizations in the region, as well as Colombian President Gustavo Petro in October (see 2510240040).
It's also unclear how fast the U.S., through sanctions relief, will be able to persuade oil and gas companies to return to Venezuela, Holland & Knight said, considering the “significant time and resources required to bring Venezuela's systems back online.” It specifically said American companies likely will hesitate to rely on any “short-term sanctions relief,” and removing sanctions altogether would hurt U.S. leverage over the current Venezuelan government.
Even if the U.S. provides Venezuela widespread sanctions relief, the firm noted, financial institutions, insurance companies and others will be “leery of reengaging in the country until the political and economic situation has stabilized. U.S. businesses are likely to be even more wary of investing in Venezuela, given the U.S. government's history of offering and revoking sanctions authorizations.”
Sidley said the U.S. likely will need to roll back at least some existing sanctions against Venezuela to get U.S. companies to reenter that market. But the firm also noted that Secretary of State Marco Rubio said the U.S. plans to keep sanctions in place until it sees a marked shift by the current Venezuelan government toward democracy (see 2601050056). "It may therefore take time for the United States to assess the Venezuelan government’s efforts on these fronts prior to providing sanctions relief," Sidley said.
Although the law firm stressed that it's too early to predict when or how the Trump administration might ease sanctions, it said most of those measures were "almost entirely the product of executive action," so the administration "should be able to act with relative ease and expediency" and wouldn't need congressional approval.
The U.S. could begin by issuing broad general licenses -- similar to the steps it took to lift sanctions against Syria -- or Trump could issue new executive orders to change the scope of the sanctions, Sidley said.
"For the time being, sanctions remain a significant obstacle for companies currently operating, or seeking to operate, in Venezuela."
Gibson Dunn said the U.S. could allow its oil and gas companies to expand operations in Venezuela in the near-term, followed by other sectors, such as mining and consumer products. But bringing back Venezuela's oil industry to previous levels will take "a substantial investment of time, human resources and tens of billions of dollars," and it will require finding new refining capacity.
"In short, increasing Venezuela’s oil supply, and making it accessible in the U.S., is a long-term project, though new business opportunities in Venezuela to support that project could be available in the near-term," it said.
The firm also stressed that any potential investors looking for opportunities in the country "should consider whether their investments can be protected under international treaties that remain in force with Venezuela or, alternatively, through direct agreements with the Venezuelan and/or United States government prior to re-entry."
In addition, Holland & Knight said companies should expect the Office of Foreign Assets Control to “intensify its enforcement crackdown” on investment advisers, accountants, lawyers and trust service providers -- known as "gatekeepers" -- for sanctions violations.
The agency last year imposed several fines against gatekeepers, including a penalty of more than $1 million against a lawyer (see 2512090045), nearly $11.5 million against an investment company (see 2512020056), and $4.67 million against a real estate investor (see 2511240052).
Those and other OFAC enforcement actions in 2025 “highlighted the risks of transacting with entities whose structures obscured a blocked person's interest -- a term that OFAC defines broadly,” Holland & Knight said. OFAC "repeatedly emphasized that gatekeepers must undertake robust diligence that looks beyond mere corporate formalities."
“OFAC enforcement actions targeted players in the private equity, venture capital, real estate and legal markets -- a focus that will continue in the year ahead.”