The news that Middlesex County Sheriff James DiPaola died suddenly today was stunning and saddening. I’ll leave it to others to report on the circumstances of his passing but perhaps a short summary of his political career might be appropriate. Motivated by last week’s news of DiPaola’s retirement, I wrote a brief history of Middlesex County Sheriffs since World War Two. The DiPaola-related portions of that appear below along with a review of the late Sheriff’s electoral record as a state representative.

Ironically, DiPaola’s paths to the House of Representatives and to the Sheriff’s office were opened by the scandals of others. In 1990, Malden was represented in the House by John McNeil but he was soon engulfed by a wave of troubles. In the summer of 1991, he was accused of surreptitiously videotaping his young daughter’s 18-year old nanny while the teenager showered. While that was being investigated, McNeil was indicted on multiple counts of extortion for allegedly trying to coerce campaign contributions from a Malden businessman. Needless to say, McNeil was unavailable to run for reelection in 1992.

With an open seat, six Malden Democrats entered the 1992 primary for the Thirty-Sixth Middlesex District: Arthur Boyle, Thomas Chausse, James DiPaola, Stephen Finn, James Flanagan, and Kathy Gardner-Gill. DiPaola won by a comfortable margin, receiving 2144 votes to second place finisher Flanagan’s 1664. With no Republican on the ballot, DiPaola won the general election without opposition. DiPaola was reelected in 1994 without opposition in either the primary or the general election.

At the same time that DiPaola was running for his second term in the House, Middlesex County Sheriff John McGonigle ran afoul of the law, was indicted, convicted, and removed from office in late 1992. Republican William Weld appointed Brad Bailey, a former Middlesex Assistant District Attorney and current Assistant US Attorney, to fill the office of Sheriff until the next state election in the fall of 1996. Forsaking a run for a third term as State Representative, DiPaola joined three others in the Democratic primary for Middlesex County Sheriff. His opponents were Ed Kennedy, a former Lowell city councilor and current Middlesex County Commissioner; Ed Rideout, a probation officer from Cambridge; and Leonard Golder of Stow. DiPaola won the Democratic primary and also won the general election, receiving 310,699 votes to Bailey’s 247,397.

Because the 1996 election was only to fill the two years remaining in McGonigle’s unexpired term, DiPaola had to run again in the next state election (1998) for a full term of his own. DiPaola was challenged in the Democratic primary by former Lowell City Councilor and current Middlesex County Commissioner Ed Kennedy. DiPaola defeated Kennedy, 101,924 to 52,772 and was unopposed in the general election.

Six years later (in 2004), DiPaola was again challenged in the Democratic Primary, this time by Robert DeMoura of Chelmsford who was also a Lowell police captain, and by Brian Gillis of Lowell. DiPaola won easily and was again unopposed in the general election. In the midst of this term in the summer of 2007 when Marty Meehan resigned from Congress to become Chancellor of UMass Lowell, DiPaola briefly entered the special election to succeed Meehan but dropped out after just a few weeks.

In November 2010, DiPaola was elected to another six-year term as Sheriff. When news broke that he had retired just before the election so that he would be eligible to receive both a pension on his full salary as Sheriff, he announced that he would resign the office of Sheriff on January 6, 2011, an act that has been overcome by today’s events.