The bombshell revelation in the Sunday Globe that Middlesex County Sheriff Jim DiPaola would resign on January 6, 2011 after just winning reelection on November 2, 2010 has already prompted several posts (Here by Marie and here by me). With so many unanswered questions, much more will undoubtedly be written. In the meantime, here is a survey of the colorful cast that has filled the office of Middlesex County Sheriff since World War Two.

The first post-World War Two sheriff was Howard W. Fitzpatrick who was elected in 1948 and served until his death in 1970. The March 1, 1970 Boston Globe story about the funeral for “Howie Fitz” reads like a Who’s Who of Massachusetts politics. The story portrays Fitzpatrick (“who adopted every charity he ever came in contact with as his own”) was a force in state political, religious and charitable circles.

Five weeks after Fitzpatrick’s death, Republican governor Frank Sargent appointed John J. Buckley of Belmont as sheriff. Buckley was the statewide director of the Massachusetts Council of Crime and Correction and had previously worked for Elliot Richardson and Leverett Saltonstall. Buckley also ran (unsuccessfully) for state auditor in 1966.

Because Buckley’s appointment only lasted until the next statewide election, he ran for the office of sheriff as the Republican nominee in the Fall 1970 statewide election. His Democratic opponent was John Dever of Woburn who defeated Walter Sullivan of Cambridge, Leonard Frisoli of Watertown and Arthur Fitzpatrick of Everett. In the general election, Buckley received 264,980 votes to Dever’s 204,823.

The 1970 election was only for the balance of Fitzpatrick’s final six-year term, so Buckley had to run once again in 1974. The Democratic challenger was Walter Sullivan of Cambridge (father of the current Middlesex County Clerk of Courts). Buckley won reelection with 230,988 votes to Sullivan’s 219,332.
Although he was a Republican, Buckley ushered in many liberal reforms including work release and furloughs. He allowed the sheriff’s official residence on the grounds of the House of Correction to be used by inmates for conjugal visits. That practice stopped when the inmates broke into the sheriff’s liquor cabinet.

In May 1980, after the deadline for collecting nomination signatures had passed, Buckley announced that he would not seek reelection. With Buckley’s departure, the state Republican Party met in caucus and selected Philip Razook as their nominee. Even before Buckley’s announcement, eight Democrats were gathering signatures to run for sheriff. They were Michael McLaughlin of Arlington, the head of the prison guard’s union at Walpole; Thomas Corkery of Reading, the county dog officer; Edward Henneberry of Framingham, a 15-year veteran of the sheriff’s office; James Breslin, a supervisor at Concord Prison; Vincent Zabbo of Lowell, a Cambridge police officer; Vincent Ciampa, a Somerville alderman; and Charles Buckley, a Somerville attorney.

Henneberry, who was endorsed by the Globe, won the primary and the general election. By all accounts, he was a well-respected and capable administrator but he was tragically struck down by a fatal heart attack in November 1984 at age 49.

Early in 1985, Governor Mike Dukakis appointed John McGonigle, a senior probation officer as the next Middlesex County Sheriff. In the 1986 state election, McGonigle won a full-term without opposition in either the primary or the general election. In 1992, three Republicans sought the nomination but the winner, Michael Dever of Woburn, was defeated by McGonigle, 381,492 to 203,840.

McGonigle’s tenure has sheriff was cut short in 1994 when he was named in a Federal indictment that alleging extortion in the Middlesex Sheriff’s civil process office. By April 1994, both Governor William Weld and Attorney General James Shannon were trying to remove McGonigle from office, but the mechanism for doing that was unclear and so the sheriff retained his office until the end of 1994. In December 1994, a jury convicted him of tax fraud but were deadlocked on all other charges. Before his retrial, however, McGonigle pled guilty to a count of conspiracy to commit racketeering and was sent to prison.

To fill the now vacant office, Republican Governor William Weld appointed Brad Bailey, a former Middlesex Assistant District Attorney and current Assistant US Attorney. Bailey served as sheriff until the fall of 1996 when he appeared on the ballot in that year’s state election as the Republican nominee. Four Democrats also ran for the office in that party’s primary: James DiPaola, a former police officer and current state representative from Malden; 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 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), DiPaula 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.

Despite the turbulent nature of politics in 2010, DiPaola faced only token opposition and easily won another six year term on November 2, 2010. Unbeknownst to his constituents, DiPaola had filed his retirement papers on October 28 and had officially retired on October 29. He intended to take advantage of a liberal interpretation by the state retirement board of a law that allowed state retirees who were elected to office after their retirement to collect both their pension and their salary from their newly attained elective office. Because DiPaola retired on October 29 and was then elected on November 2, he was eligible to draw his full salary and his full pension starting in January 2011.

The sheriff’s plan went awry on November 19, 2010 when a Boston Globe reporter inquired about the arrangement. After initially defending his intentions, DiPaola changed his mind the next day and announced that he would resign the office of sheriff on January 6, 2011, right after taking the oath of office for his new term. Once the office becomes vacant, Governor Patrick will appoint a successor sheriff will serve until the 2012 state election when someone will be elected to serve the balance of the unexpired six-year term.