An attorney who worked for Prince 10 years ago is out nearly $600,000 he said was owed him from the late megastar’s multimillion-dollar estate.

Carver County District Judge Kevin Eide granted a motion Monday to dismiss the claim from Florida attorney Patrick Cousins, who said he handled Prince’s divorce from Manuela Testolini between 2004 and 2009.

Cousins submitted the claim for $599,735.63 to Bremer Trust, the former special administrator for Prince’s estate, in September. New special administrator Comerica Bank & Trust sought to dismiss the claim, arguing that the special administrator had already rejected it and Cousins had missed the deadline for challenging that decision.

Cousins said he met all requirements to collect the money under Minnesota law.

In his order, Eide wrote that Cousins’ legal challenge is a dead issue under state law because it was filed “at least 43 days after it was due.”

Prince died April 21 of an accidental overdose of the painkiller fentanyl.