Robert “Bob” Ross advises businesses and other organizations in a wide range of complex regulatory, governance, and transactional matters. He assists both established and emerging businesses and nonprofits looking to do business in Massachusetts, especially those in highly regulated areas, such as insurance, gaming and energy.
Bob represents public entities, private businesses, and nonprofits in navigating Massachusetts’ regulatory landscape, with particular experience in litigation, agency proceedings, and public law matters. His work includes representing the Commonwealth of Massachusetts and the City of Leominster in high-stakes litigation involving hospitals and eminent domain, and guiding life and health insurers through compliance challenges such as Division of Insurance approvals and the implementation of new “junk fee” regulations. Bob advises gaming licensees on unfair trade practices litigation and regulatory waivers and has helped form public benefit corporations like the Massachusetts Mobility Hub. He also counsels restaurants and other businesses on labor and employment disputes before state agencies. Through this diverse practice, Bob helps clients achieve their strategic objectives while navigating complex regulatory requirements.
Bob has over 20 years of experience advising senior government leaders in a variety of state government roles in the Commonwealth of Massachusetts. Bob served as chief legal counsel in the office of Massachusetts Governor Charles Baker throughout the Governor’s second term of office. In this role, he oversaw a team of in-house attorneys and advised the governor’s office and state agencies on myriad issues, including the Commonwealth’s COVID-19 pandemic response. He also oversaw litigation and approved settlements on behalf of the Commonwealth. In his previous role as general counsel in the Executive Office for Administration and Finance, Bob was deeply involved in the preparation of five annual state budgets.
Bob served in the Office of the Senate President when Massachusetts legalized casino gaming, and as Chief Legal Counsel when former Governor Baker drafted, and then approved, legislation authorizing sports wagering in Massachusetts. In both instances, he advised elected leaders on issues relating to the expansion of gaming in the Commonwealth. With Greenberg Traurig, he has assisted clients with licensing issues before the Massachusetts Gaming Commission.
As assistant attorney general and chief of the Massachusetts Business and Labor Bureau, he supervised the regulation and enforcement of various laws governing a wide variety of businesses in Massachusetts. Bob’s other state governmental roles have included chief policy advisor for the Office of the Senate President, counsel and budget director for the Committee on Ways and Means, and counsel for the Division of Insurance, State Rating Bureau.
