After graduating from Brown in 1951, Herb entered Columbia University Law School from which he received his degree in 1954. Shortly thereafter he was admitted to the Rhode Island Bar to begin a legal career that spanned six decades.
In 1966 Herb ran as a Republican for attorney general as part of a formidable slate of general offices headed by Governor John Chafee. He won election by a comfortable margin over longtime incumbent J. Joseph Nugent running on a diverse platform of legal reforms that he crafted in conjunction with political advisor Dr. Patrick T. Conley.
After gaining re-election in 1968, DeSimone ran for the governor’s seat vacated by Chafee but lost to Superior Court Judge Frank Licht. Shortly after that setback, President Richard Nixon appointed DeSimone Assistant Secretary of Transportation for the Environment and Urban System. He stepped down from that post in 1972 to make another run for governor, but he lost that contest to Warwick Mayor Philip Noel.
In August, 1976 President Gerald Ford nominated DeSimone to succeed Judge William Day as a Rhode Island federal district judge, but that nomination was blocked by Democrat U.S. Senator Edward K Kennedy. He then returned to private practice in a firm where he would eventually be joined by his sons Herbert Jr. and Douglas. Although DeSimone did not run for public office again, his influence and stature was undiminished. Of particular importance was his relationship with a rising protègè who had worked as a volunteer in his campaigns from 1966 onward and who served in the attorney general’s office during DeSimone’s tenure. That pupil was Vincent A. Cianci who in 1974 won the Providence mayoralty by beating longtime incumbent Joseph A. Doorley, Jr.
In future years, with Cianci’s backing, Herb served as Director of the Providence Industrial Development Corporation and as General Counsel for the Rhode Island Housing and Finance Corporation. DeSimone’s continued prominence in the Republican Party was evidenced in 1985 when Governor Edward DiPrete appointed him Director of the Rhode Island Department of Transportation.
DeSimone was not merely a successful politician, he was an able, bright, and talented attorney. In 2002 he received the Neil J. Houston Award for his contributions to the criminal justice system and, as a proud Italian- American, he received the Man-of-the Year Award from the Italo-American Club of Rhode Island.
Herb had a long and successful marriage to Sally Reynolds, daughter of Charles Reynolds, former Providence College baseball star, former Democrat mayor of Pawtucket, and East Providence City manager. Despite their different political backgrounds Sally and Herb got along harmoniously and produced three successful children: Deborah and attorneys Herbert and Douglas.
DeSimone’s long and highly successful career ended on November 27, 2013 at the age of eighty – four. He was buried in Pawtucket’s St. Francis Cemetery.