Bob attended Middlebury College and Columbia Law School, where he was a Stone Scholar. He was admitted to the Massachusetts Bar in 1961 and the Maine Bar in 1991. During his practice in Massachusetts, Bob served as a Law Clerk to Justice J.J. Spiegel of the Massachusetts Supreme Judicial Court, and associate counsel in the Law Department of New England Mutual Life Insurance Company. He practiced for twenty years with the Boston law firm of Hale and Dorr where he was a senior partner in the real estate department and represented lenders and developers in transactions involving commercial properties of all kinds.
With the onset of the deep recession in real estate in the late 1980’s, Bob’s practice shifted principally to the representation of banks and other lenders burdened by troubled loans and equity investments. Bob joined Drummond & Drummond in 1993. During the period of recovery for commercial real estate, his practice concentrated on the representation of lenders and institutional owners in the management, leasing and disposition of owned real estate. Under his direct supervision, the firm closed over 95 sales and over 400 lease transactions involving office, industrial and retail properties in 30 states and the District of Columbia.
More recently, Bob has been involved with a broad range of real estate matters, but still with an emphasis on commercial property. Since becoming Of Counsel to the Firm, Bob has continued to be actively involved with the representation of his clients, and acts as consultant on real estate issues.

About Bob

Bob and his wife live in South Freeport, Maine. He is an avid sailor and occasional skier. Bob is a trustee of the Freeport Land Trust to which he devotes his pro bono efforts.


  • Columbia Law School
  • Middlebury College

Bar Admissions

  • Maine (1991)
  • Massachusetts (1961)