Before retiring from the bench in 2022, Judge Drain oversaw proceedings ranging from large Chapter 11 corporate restructurings — including Loral, RCN, Cornerstone, Refco, Allegiance Telecom, Delphi, Coudert Brothers, Frontier Airlines, Star Tribune, Readers Digest, A&P, Hostess Brands, Christian Brothers, Momentive, Cenveo, 21st Century Oncology, Tops, Global A&T, Sears, Full Beauty Brands, Sungard, Windstream, Purdue Pharma, Jason Industries, OneWebb and Frontier Communications — to Chapter 15 and other cross-border cases, such as Varig, S.A., Yukos (II), SphinX, Galvex Steel, TBS Shipping, Excel Maritime, Nautilus, Landsbanki Islands, Roust and Untrapetrol. He also served as a court-appointed mediator in numerous cases, including New Page, Cengage, Quicksilver, Advanta, LightSquared, Molycorp, Breitburn Energy, China Fishery and PREPA.

In his current practice at Skadden, he advises on U.S. and cross-border Chapter 11 and 15 reorganizations and litigation, out-of-court restructurings, distressed M&A and investments in troubled companies, debtor-in-possession loans and exit financings, as well as potential examiner or trustee roles and mediations.

Judge Drain is a fellow of the American College of Bankruptcy, a member and former board member of the American Bankruptcy Institute (ABI), and a former board member and officer of the National Conference of Bankruptcy Judges (NCBJ). He was chair for several years of the Bankruptcy Judges Advisory Group established by the Administrative Office of the U.S. Courts, has testified before the Senate Judiciary Committee on home mortgage loss mitigation, and currently serves on the FDIC’s Systemic Resolution Advisory Committee. He was a founding member and chair of the Judicial Insolvency Network, which developed, among other issuances, guidelines that were adopted by courts in the U.S. and abroad for cooperation and communication in concurrent transnational insolvency cases. He also long annually presided over a mock transnational bankruptcy case for the International Association of Restructuring, Insolvency & Bankruptcy Professionals’ (INSOL’s) training program and is a member of the International Insolvency Institute. He is a member of the Business Bankruptcy Committee of the U.S. Bankruptcy Court for the Southern District of New York.

Judge Drain is an adjunct professor at Pace University School of Law and a former adjunct professor in St. John’s University School of Law’s LL.M. in Bankruptcy Program. He has contributed to treatises on bankruptcy law and frequently lectured on bankruptcy law in multiple programs for the Federal Judicial Center, NCBJ, ABI, AIRA, Turnaround Management Association, Practising Law Institute, American College of Bankruptcy, International Insolvency Institute, Federal Bar Council, Columbia University School of Law and national, international and local bar associations, as well as judicial and professional interchanges with judges and practitioners in South America, Europe, China, South Korea, Singapore and India.

Prior to his time on the court, Judge Drain spent nearly 20 years in private practice, including 10 years as a partner in the bankruptcy and restructuring practice of another global law firm.