A New York federal judge on Friday ordered Martin Shkreli to pay nearly $65 million and banned the disgraced former executive from ever working in the pharmaceutical industry again, siding with Attorney General Letitia James in a high-profile lawsuit stemming from his move to dramatically raise the price of a life-saving drug in 2015.

U.S. District Judge Denise L. Cote said in a 135-page opinion that Shkreli, whose exploits once gave him the derogatory moniker “Pharma Bro,” violated state and federal laws in exerting monopoly power over Daraprim, which is used to treat parasitic infections and HIV.