Was it a $226,000 loan or a quarter-million dollar gift? This week, a U.S. District Court judge will decide if Garth Brooks is due the sum from Lisa Sanderson, a former employee and friend.

The singer’s lawsuit is the latest in a series of lawsuits and disagreements with Sanderson, the one-time CEO of Red Strokes Entertainment, Brooks’ television and movie production company. Last year, she sued him for $425,000 in unpaid bonuses and salary, as well as punitive damages. That trial, which is separate, is to take place in Los Angeles Superior Court, but the date has not been set.

Most documents related to Brooks’ case against Sanderson are sealed, according to the Tennessean. However, one memorandum claims he took care of legal fees related to a custody battle she was going through between 2005 and 2007. The lawsuit says the money he is seeking was transferred between his lawyers and her lawyers during these years.

“Mr. Brooks stated in numerous occasions that he too was deeply concerned about Sanderson’s son’s welfare,” a memorandum prepared by her attorney states. “For that reason he wanted to take care of any legal fees Sanderson incurred in connection with the custody dispute. Mr. Brooks reassured Sanderson over and over again that ‘it was all about Ben’ and that Sanderson would never have to repay him for the legal fees. ...”

A statement from Brooks about the nature of the money transfer was not made available. This week's case is expected to last three days, and Judge Aleta Trauger will preside over the proceedings.

It's been a country music-filled two months for Judge Trauger. Late last year, she dismissed Brad Paisley, Carrie Underwood and others' request for dismissal in a case revolving around the song 'Remind Me.'