About Robert L.
Robert L. Flanagan earned a B.A. in economics from Harvard University in 1963 and a J.D. from Cornell University in 1971. He trained in two different academic traditions and then moved into a mix of private practice and public service. The academic record frames a career that alternates between courtroom work, firm responsibilities and state government roles.
Flanagan began his post-law-school career in private practice. He worked as an associate at Robinson and Cole from 1974 to 1977. He then served as a senior litigation lawyer at the United States Railway Association from 1977 to 1979, a role that placed him squarely in transportation-related legal work early in his career.
From 1979 to 1985 Flanagan was a litigation lawyer at Saul Ewing, where he handled a range of civil litigation matters. He joined Siskind, Burch, Grady and Rosen as a partner and lead litigation lawyer from 1985 to 1987. During the mid-1980s he was also involved with the Howard County Human Rights Commission, serving as a member in 1985 and 1986.
In 1987 Flanagan opened his own practice. From 1987 to 2003 he listed the Law Office of Robert L. Flanagan as his professional base. Those same years saw him serve as an elected member of the Maryland House of Delegates. He balanced private practice with legislative responsibilities for more than a decade and a half, handling both casework and the demands of public office.
His public-sector career expanded in 2003 when he was appointed Secretary of the Maryland Department of Transportation, a post he held until 2007. That position placed him at the intersection of state government and large-scale transportation projects. After leaving the department he moved into the private financial sector as a senior vice president at First Southwest Company from 2007 to 2009. In 2009 he resumed private practice and is listed as the owner of the Law Office of Robert L. Flanagan through the present.
Across a long career Flanagan has alternated between litigation roles and positions that required engagement with government operations and infrastructure matters. He has handled courtroom work, firm leadership and administrative duties in state government. He focuses his current practice on civil litigation, administrative matters and advising clients on issues arising from government and transportation projects.
