Pras Michel, a founding member of the Fugees and the first hip-hop artist to be convicted on charges of working as a covert agent of the Chinese government, hasn’t entirely run out of ways to avoid going to federal prison, but he’s getting close. On the Friday before Labor Day, Judge Colleen Kollar-Kotelly issued her lengthiest ruling on the case since Michel was first indicted in 2019 on conspiracy charges for money laundering and election-law violations. Following Michel’s conviction last year, he upgraded to new lawyers, who immediately went after his prior attorney, former Death Row Records counsel David Kenner, for allegedly doing such a poor job defending Michel that he violated his right to a fair trial.

Known as an “ineffective assistance of counsel” claim, it was one of more than a dozen arguments made by Michel’s new team for why he deserves a retrial . In her 77-page ruling, Judge Kollar-Kotelly responded to them all with one consistent and resounding message: nope. “We’re disappointed with the decision,” Michel’s lead attorney Peter Zeidenberg said.

“We think there were grievous and serious errors in the trial and they impacted the fairness of the outcome, and we will be appealing.” Media attention has focused on the fact that Kenner used experimental AI software to draft a bizarre closing statement at Michel’s trial last year; the chatbot’s glitchy hallucinations misattributed two chart-topping tracks, Puff Daddy’s “I’ll Be Missi.