A California federal judge’s order may bring to a close a nearly 20-year court battle as the estate of Playboy model Anna Nicole Smith fights for money from the estate of her billionaire husband, J. Howard Marshall II of Houston.

On Aug. 18, U.S. District Judge David Carter of the Central District of California denied a motion for sanctions filed by the estate of Texas native Smith, also known as Vickie Lynn Marshall. The sanctions motion filed by Smith’s estate sought $44 million from the estate of Pierce Marshall, a son of J. Howard Marshall who inherited his estate.