A federal judge is set to decide whether to impose sanctions of up to $44 million against the estate of Anna Nicole Smith’s former stepson.

The sanctions come in a claim originally filed by E. Pierce Marshall, the son of Smith’s late husband, Texas oil tycoon J. Howard Marshall, against the former Playboy model, who had filed for U.S. bankruptcy protection. The younger Marshall died in 2006 and Smith died of a drug overdose in 2007.