An attorney who handled Prince's divorce and some business transactions nearly a decade ago is seeking $600,000 in unpaid bills from the artist who died from an opioid overdose last year.

In Carver County District Court Friday, the company managing Prince's estate argued that Florida attorney Patrick Cousins' debt claim had already been rejected by the special administrator and that Cousins had missed a deadline to legally challenge the decision.

Cousins said that he and attorneys based in Minnesota carefully read state statute and that he met all the requirements to collect the $600,000. Judge Kevin Eide said he would rule on the motion next week.

From 2004 until 2009, Cousins said, he handled Prince's second divorce, from Manuela Testolini. The musician had consistently paid his bills to Cousins, and Prince never denied he was going to pay the rest of his tab, Cousins said.

"Nobody knew [Prince] was going to die when he did," he said. "I was in shock when I heard the news."

Prince died of an accidental fentanyl overdose at Paisley Park studio on April 21. Six relatives are expected to be heirs. Attorneys working the case have said it's the most complex estate transaction in Minnesota history. No will has been found, and more than 1,000 documents have been filed in his case.

The estate is conservatively estimated at nearly $300 million. Comerica Bank & Trust recently became the estate's special administrator.

Joseph Cassioppi, who represented Comerica at Friday's 30-minute hearing, said Cousins had two months after his claim was rejected to challenge the decision. He also said incorrect paperwork was filed in the case.

Cousins said he knew Prince was a private person and it pains him to drag this issue out in public.

"I drove by Paisley Park last night," he said. "It just felt different driving here."