The Rabbit Hole: Chasing Shadows

Editor’s note: The success of a healthy world economy relies heavily on countries accepting a series of norms. For today’s The Rabbit Hole, reporter Peter Beck takes us through the legal consequences of the growing shadows that cast over global trade. -Seamus 

On December 20, 2025, an oil tanker flying a Guyanese flag was navigating through the Caribbean Sea when a U.S. Coast Guard cutter emerged. The tanker, called the Bella 1, had a course set for a Venezuelan port, where it would pick up oil, just as tensions between the U.S. and the Maduro regime appeared to be heading toward an inflection point. Four days earlier, on December 16, President Trump had declared what he called a “TOTAL AND COMPLETE BLOCKADE OF ALL SANCTIONED OIL TANKERS.”

On social media, Trump wrote, “Venezuela is completely surrounded by the largest Armada ever assembled in the History of South America. It will only get bigger, and the shock to them will be like nothing they have ever seen before—Until such time as they return to the United States of America all of the Oil, Land, and other Assets that they previously stole from us.”

The Bella 1 was about to put that armada to the test. The Coast Guard announced its presence, ordering the Bella 1 to cut its engine and submit to a boarding party. The Coast Guard had a warrant to seize the boat and its cargo. The Bella, however, didn’t respond. It kept sailing, beginning a high-stakes chase that would draw international attention as the peoples of Venezuela and the United States anxiously waited to see if the runaway tanker would trigger a war.

Now, the man who captained the tanker is set to be sentenced in a U.S. district court. On Friday, Judge Beryl A. Howell will decide whether to send Avtandil (“Avto”) Kalandadze to a federal prison or back to his native Georgia. 

For the first time, federal court records tell the story of the Bella 1’s captain and the rest of its crew. To federal prosecutors, Kalandadze is the man who defied U.S. forces and put their lives at stake, while in control of a tanker at the heart of a shadow network of assets that fills U.S. enemies’ coffers. At the time of his guilty plea, U.S. Attorney Jeanine Pirro noted, “This defendant [Kalandadze] put American sailors’ and Coast Guardsmen’s lives at risk while attempting to evade U.S. sanctions and move illicit oil. By refusing lawful orders from the U.S. Coast Guard and leading them on a chase across the Atlantic Ocean, he not only obstructed federal law enforcement, but forced our service members to carry out a dangerous boarding operation in heavy seas.”

Conversely, Kalandadze’s defense attorneys paint a compelling picture of a man who found himself on the wrong boat, at the wrong time, and who selflessly sacrificed for his family and crewmates, time and time again. Defense motions, by their very nature, show a client in the most favorable light. In their sentencing memo, his attorneys describe how Kalandadze ended up at the heart of an international crisis and argue the most just punishment is to send him home. 

The 47-year-old Kalandadze, according to his attorneys, is the eldest son of a civil engineer and a teacher, whose compassion and sense of duty apparently wore off on Kalandadze. Growing up in Georgia, Kalandadze’s school and college years coincided with the economic shocks brought by the deterioration and then dissolution of the Soviet Union. Rather than hunker down and conserve resources, Kalandadze’s parents welcomed their displaced friends and community members into their home. 

Kalandadze, meanwhile, always dreamed of becoming a sailor. He attended a maritime academy in Georgia before serving in the country’s navy. He had a knack for it, rising through the ranks steadily until 2020, when he was promoted to captain. One of his colleagues, in a letter addressed to Judge Howell, wrote that he had “never met anyone as . . . dedicated to his profession as Avtandil.” In another letter, his mother wrote, commending how, “through selfless dedication, continuous study, and unwavering commitment to his goal, he achieved the highest rank—that of Captain.” Kalandadze went on to receive a master's in navigation.

He sailed across the globe. All the while, he sent money back home, supporting his parents, siblings, family friends, wife, and kids. When he was home, his defense attorneys and letters sent to Judge Howell describe incredible acts of bravery: On two separate occasions, he dove into rough waters to rescue people in danger of drowning. In another instance, he reportedly delivered first aid to a neighbor’s child during an emergency. 

Kalandadze initially found work through contracts with crewing agencies, which connect sailors to shipping companies. But the war in Ukraine hurt the Georgian shipping industry. The imposition of Western sanctions against Russia restricted where ships could go and what they could carry. Even the safety of the ships themselves was now a question, with fighting between Ukraine and Russia spilling into the Black Sea. Insurance and other operating costs rose. Shipping contracts dried up. 

His attorneys say Kalandadze was out of work for more than a year, unable to give the usual financial support to his three-generation family and friends.