Just a few days before the Supreme Court hears arguments on the legality of President Donald Trump’s use of the International Emergency Economic Powers Act (IEEPA) to impose global tariffs, prediction markets are signaling a slightly better-than-even chance that the justices will rule against him.
Two separate betting sites — one asking whether Trump will lose, the other whether he’ll win — show about a 60% chance he’ll lose. Odds on PredictIt jumped to 66% on last week after hovering between 48% and 69% for the past month. Polymarket’s odds have stayed steady since late September, with the latest reading showing around a 60% likelihood that the president won’t prevail.
Both sides will present arguments at the November 5 hearing, though a final decision isn’t expected until early 2026. Trump, calling the case “one of the most important in the country’s history,” has hinted he may attend personally. He hopes to preserve the broad tariff powers he invoked on “Liberation Day” in April, when sweeping duties were imposed under IEEPA.
A High-Stakes Backdrop
IEEPA was enacted in 1977 to give presidents emergency powers to regulate international economic transactions, not to levy tariffs wholesale. Lower courts have already ruled that using IEEPA to impose broad import duties exceeds executive authority. The Supreme Court’s decision will determine whether the administration can continue to use “emergency powers” as a standing trade policy tool.
The Court of International Trade struck down much of the program in May, and the Federal Circuit affirmed that ruling in August while granting a stay to allow Supreme Court review. Billions in duties — and potentially tens of billions in refunds — now hang in the balance.
Betting on Refunds
If Trump loses, American importers that paid IEEPA-based tariffs could be entitled to refunds, fueling a new wave of financial speculation. According to Bloomberg, Jefferies and Oppenheimer are among banks brokering deals between investors and importing companies, matching investors who bet the tariffs will be struck down with importers seeking cash now.
In these arrangements, importing firms sell future rights to any refund at a discount; investors take the upside if the Supreme Court invalidates the tariffs, while banks take a cut for arranging the trades.
But trade lawyers warn these transactions could be legally shaky — or, in the words of New York attorney Michael Cone, “a total mess.”
Under federal law, only the importer-of-record can file or receive a refund because that entity paid the duties. Assigning or transferring such claims before the amount is determined may violate federal statute. If refunds are ordered, importers who sold their rights could challenge those contracts in court — and investors could respond with their own lawsuits.
As Cone notes, “Because the Supreme Court hasn’t yet ruled on whether or how much will be refunded, there’s a reasonable argument these transfers are premature.”
Key Timeline
- April 2, 2025 — “Liberation Day”: Trump invokes IEEPA to impose sweeping emergency tariffs.
- May 28, 2025: Court of International Trade rules the action unlawful.
- August 29, 2025: Federal Circuit upholds the ruling but stays enforcement.
- November 5, 2025: Supreme Court hearing scheduled.
- Q1 2026 (expected): Final decision and possible refund guidance from CBP.
What Importers Should Do Now
- Preserve rights. File or verify protests and post-summary corrections (PSCs) on all IEEPA-tariffed entries.
- Quantify exposure. Identify duties paid under IEEPA orders — by HTS, country, and period.
- Document everything. Keep entry summaries, invoices, broker communications, and payment proof.
- Avoid risky assignments. Be cautious of offers to “sell” your refund rights — these could invite legal complications.
- Plan for contingencies. Model cash-flow outcomes for each scenario: upheld, narrowed, or invalidated.
The Road Ahead
Whether the Court sides with the administration or the challengers, the decision will redefine the reach of presidential trade powers — and reshape compliance planning for importers for years to come. If the tariffs fall, the scramble for refunds could rival anything seen in customs litigation in decades.
Our compliance and consulting teams are monitoring the Supreme Court case and its potential implications in real time. We will continue to keep you posted on developments.