In a long-running legal fight over a Nazi-looted painting by French impressionist master Camille Pissarro, a federal judge in Los Angeles on Tuesday sided with the Spanish Foundation who currently holds the painting over the heirs who were seeking to reclaim it.

The parties in the case agreed that Lilly Cassirer Neubauer, the great-grandmother of the Cassirer plaintiffs, sold Pissarro's “Rue Saint-Honoré, après-midi, effet de pluie” in 1939 after a Nazi-appointed art dealer seized it to conduct an appraisal and valued it at the modern equivalent of $360. The masterpiece since has been appraised at more than $30 million.

U.S. District Judge John Walter on Tuesday held in a 34-page order that Madrid-based Thyssen-Bornemisza Collection Foundation (TBC), which manages the collection of art acquired by the Spanish state that includes the Pissarro, didn't have “actual knowledge” that the painting was stolen despite “red flags” that might have raised suspicions about the painting's record of ownership.