Judge Bailey served as judicial law clerk to the Honorable Herbert P. Wilkins of the Massachusetts Supreme Judicial Court in 1980-81. He was an associate at the Boston office of Sullivan & Worcester LLP until 1987 where he practiced in the litigation and corporate restructuring departments. He spent the next twenty-two years as a partner at the firm of Sherin and Lodgen LLP where he served as the Chairman of the Litigation Department and as a member of the firm's management committee. At the firm, his practice focused on complex business litigation and business bankruptcy. He often represented clients in the medical device, pharmaceutical and high technology businesses.
Judge Bailey was appointed by the First Circuit to oversee the financial restructuring of the City of Central Falls, Rhode Island, a rare Chapter 9 case. The City of Central Falls filed a contested plan of readjustment that was confirmed in a little more than a year from filing.
pJudge Bailey serves on the Board of Governors of the National Conference of Bankruptcy Judges and in 2016 is the in-coming chair of the National Conference of Federal Trial Judges of the American Bar Association. In addition, he serves on the Standing Committee on Diversity in the American Judiciary of the Judicial Division of the American Bar Association.