Thomas Califano

Practice Areas

Tom Califano is a partner in Sidley’s New York office and a key member of the firm’s Restructuring group, with a national reputation for his work in complex healthcare, energy, and financial services restructurings. He has written and lectured extensively on the subject and has been invited to address several judicial conferences.

Tom has played a lead role in some of the most significant recent Chapter 11 cases, including representing Prospect Medical Holdings — one of the largest Chapter 11 filings of 2025, involving more than US$2.2 billion in funded debt — and guiding CareMax and its 53 affiliated debtors through Chapter 11 proceedings in the U.S. Bankruptcy Court for the Northern District of Texas. Tom led the cross-border, multidisciplinary Sidley team advising Ebix, a publicly traded global software and e-commerce provider , in its Chapter 11 cases filed in December 2023 in the U.S. Bankruptcy Court for the Northern District of Texas.

Tom’s practice has a particular emphasis on company- and buyer-side representations. Tom has been recommended by The Legal 500 U.S. for his “excellent reputation across all aspects of in and out of court restructurings.” For over a decade, he has been recognized annually by Chambers USA for his work in Bankruptcy/Restructuring, where he is described as “an outstanding attorney,” and “a very strategic adviser around the restructuring process” whose “intelligence, experience and compassion guarantee the best results.” Tom is also lauded as “a genius who will make sure the client’s interests are best protected,” and “an aggressive and fierce advocate for his clients” with an “expertise in advising financially troubled companies and buyers of distressed assets.”

Prior to joining Sidley, Tom was the global co-chair and U.S. chair of the restructuring group at another global law firm.