In a somewhat unexpected development given his recent appointment to a second 14-year term a mere 5 years ago, Bankruptcy Judge Robert D. Drain of the U.S. Bankruptcy Court for the Southern District of New York announced that he intends to retire as of June 30, 2022. Judge Drain has presided over many large, high-profile chapter 11 cases, most recently the Purdue Pharma bankruptcy proceedings, in which he confirmed the debtors’ proposed chapter 11 plan, including releases of non-debtor Sackler family members, over the objections of the U.S. Trustee and numerous other stakeholders. Other major cases that Judge Drain has presided over include Momentive, Sears, Frontier Airlines, Windstream, and Frontier Communications. Among other things, Judge Drain was well known for his willingness to confirm prepackaged chapter 11 plans of reorganization sometimes within days or even hours of case filing, provided the debtor could establish that creditors would not be harmed by the speed of the proceedings. It will be up to the U.S. Court of Appeals for the Second Circuit to select a new bankruptcy judge to fill the vacancy left by Judge Drain’s departure.