U.S. authorities are intensifying scrutiny of Greek shipowners and maritime companies over suspected dealings involving Iranian oil and other sanctioned commodities, bringing several shipping businesses under investigation and raising the prospect of substantial financial penalties.
Among the companies facing regulatory pressure is Athens-based Times Navigation, controlled by Greek shipowner Yannis Karageorgis, which is challenging a proposed $4.075 million penalty from the U.S. Treasury Department over shipments of Iranian-origin metals and minerals.
The dispute has reached federal court in Washington, where the company is contesting the Treasury Department's authority to pursue the penalty through its administrative enforcement process.
The case comes amid broader U.S. efforts to disrupt shipping and financial networks suspected of facilitating trade involving sanctioned Iranian entities.
Recent American sanctions announcements have also identified Greek shipowners Alberto Tsoris and George Tsoris in connection with Shipoil Limited, Shipoil FZCO and Ship Fuels and Trade DMCC, companies accused by U.S. authorities of commercial dealings involving sanctioned Iranian counterparties.
The law firm Karnakis and Karnakis, which operates in Greece and Panama, has also been cited in connection with alleged services provided to shipping structures linked to Iranian sanctions activity.
Separately, U.S. authorities are examining whether Greece's Aegean Baltic Bank processed transactions involving entities under scrutiny for their Iranian connections, according to the Greek report.
The allegations and investigations involve separate parties and shouldn't be interpreted as findings of wrongdoing against all those named.
Eleven Shipments Under Scrutiny
The Times Navigation dispute centers on transactions dating back nearly eight years.
According to U.S. court documents, the Treasury Department's Office of Foreign Assets Control, or OFAC, is examining 11 shipments of Iranian-origin metals and minerals transported between April 26, 2018, and March 5, 2019.
The cargoes were carried aboard three vessels involved in sale-and-leaseback arrangements between Times Navigation and U.S. investment company YieldStreet Inc.
Under those arrangements, the vessels were sold and subsequently leased back, allowing Times Navigation to continue operating them.
U.S. authorities allege that the shipments, undertaken for third-party charterers, resulted in violations of American sanctions restrictions by YieldStreet.
The transactions created the basis for OFAC's proposed enforcement action against Times Navigation, illustrating how commercial arrangements involving U.S. financial interests can expose foreign shipping companies to American sanctions scrutiny.
A $4.075 Million Penalty
On May 19, 2026, the Treasury Department issued a formal notice of proposed penalty to Times Navigation, addressed personally to Karageorgis in his capacity as chief executive at the company's Athens offices. The notice, identified as enforcement case ENF 973329, alleged conduct prohibited under U.S. sanctions regulations and proposed a civil monetary penalty of $4.075 million. OFAC classified the alleged violations as particularly serious, a determination that influenced the proposed penalty.
Times Navigation responded by challenging the enforcement process itself. On July 2, the company filed a lawsuit in federal court in Washington against Treasury Secretary Scott Bessent, OFAC official Bradley Smith and the Treasury Department. The company argued that OFAC lacked the constitutional authority to impose such penalties without prior judicial adjudication and sought an injunction temporarily halting the administrative proceedings. On Aug. 31, U.S. District Judge Beryl A. Howell denied that request, finding that Times Navigation hadn't demonstrated the irreparable harm necessary to justify preliminary relief. The ruling didn't resolve the underlying allegations or determine whether the proposed penalty was warranted.
The legal battle subsequently moved into a new phase, with both sides seeking judgment on the central legal questions without a full trial. The Treasury Department filed its motion on Sept. 4, followed by responses from Times Navigation on Sept. 9 and the government on Sept. 16.
In September, Times Navigation strengthened its legal team by bringing in Cari Stinebower, an American attorney with more than 25 years of experience in economic sanctions, anti-money-laundering regulation and international trade. Stinebower previously worked at the Treasury Department, where she participated in sanctions policy development and defended OFAC in litigation. Her experience includes advising financial institutions, shipping companies and multinational businesses on sanctions involving Iran, Russia, Venezuela and Cuba.
