An 11-year-long legal dispute over a prized Amedeo Modigliani painting looted during World War II has concluded in a loss for billionaire art dealer David Nahmad and his family, marking an unlikely restitution victory for the heirs of its original Jewish owner.

A New York judge ruled this week that Seated Man With a Cane (1918) rightfully belongs to the estate of Oscar Stettiner, a Jewish art dealer who left the portrait behind under duress while fleeing Paris ahead of the Nazi occupation. The court found that the painting was illicitly seized and illegitimately transferred, rejecting the Nahmads’ longstanding argument that its provenance, or ownership history, was unclear.