Britney Spears’ father received a loan of at least $40,000 from a firm he later put in charge of his daughter’s business affairs, according to an investigation from The New York Times. The loan, made by Tri Star Sports & Entertainment Group, was made less than a month before Jamie Spears filed to have Britney placed under a conservatorship in 2008. After the conservatorship was approved, Spears, who had been cash-strapped and struggling with alcoholism, sent Britney on tour. Tri Star and owner Louise M. Taylor were hired to run her estate.

Mr. Spears’ lawyer, Alex M. Weingarten, initially told the Times that Britney’s father “never” received a loan from Tri Star. He later confirmed that his client, in fact, had been floated the cash, adding, “Tri Star routinely loans money to clients.” The president of the National Guardianship Association told the Times that the arrangement “reeks of conflict of interest,” asking, “Is the conservator making decisions in the best interest of the conservatee or the business manager they owe a debt to?” Though her lawyer, Mathew Rosengart, is still investigating, it remains unclear how much money Tri Star made from the deal over the years.