Recent History of the Massachusetts Speaker of the House
Whether you’re a new activist, a veteran lobbyist or just a curious citizen, here at InstaTrac we aim to keep you up to date and well informed on everything happening on Beacon Hill. In this week’s blog we’re shining a light on the most powerful and historically controversial position in the General Court: The Speaker of the House.
The Speaker isn’t just a figurehead — as the presiding officer of the House, they hold enormous influence over the flow of legislation. From handpicking committee chairs and co-chairs, to deciding which bills make it to the floor and which ones quietly disappear, the Speaker operates with sweeping authority.
Massachusetts has had not one, not two, but three consecutive speakers of the House become convicted felons, a streak that earned the position a bit of an infamous streak in the 2000s.
Charles Flaherty (D-Cambridge) (Speaker 1991–1996): Tax Trouble and Lobbyist Freebies
Charles Flaherty served as Speaker during a time when lobbying practices were under increasing scrutiny and unfortunately, he was a textbook example of what not to do. In 1996, he pled guilty to felony tax evasion after failing to report thousands of dollars in rental income on his tax returns. But that wasn’t all. He also admitted to civil violations of the state’s conflict of interest law, including accepting free vacation stays from lobbyists who were trying to influence legislation.
Thomas Finneran (D-Boston) (Speaker 1996–2004): Drawing the Lines, Then Crossing Them
Thomas Finneran, Flaherty’s successor, was known for his tight grip on the House that left little room for dissent. But it was his handling of the redistricting process following the 2000 Census that led to his legal troubles.
Finneran claimed under oath that he had little involvement in drawing new legislative maps. But evidence later showed he had been intimately involved in crafting district boundaries that were widely criticized for diluting minority voting strength. In 2007, Finneran pled guilty to obstruction of justice for making false and misleading statements to a federal court about his role in the redistricting case. Though he also avoided prison, the plea cost him his license to practice law.
Salvatore DiMasi (D-Boston) (Speaker 2004–2009): A Software Scheme with a $13 Million Price Tag
Sal DiMasi followed Finneran and initially positioned himself as a reformer. But behind the scenes, he was orchestrating a scheme that would ultimately land him in federal prison. At the heart of the case was Cognos, a Canadian software company that sought a lucrative state contract for a performance management system.
Prosecutors alleged that DiMasi used his power to steer state contracts worth more than $13 million toward Cognos, in exchange for kickbacks totaling more than $65,000, funneled through shady third-party payments to a friend and business associate. In 2011, DiMasi was convicted on seven federal counts, including conspiracy, extortion, honest services fraud, mail fraud, and wire fraud.
He was sentenced to eight years in federal prison, serving five before being released in 2016 on compassionate grounds due to health issues. As the third straight Speaker to be convicted of crimes committed in office, It was an unprecedented streak of scandal, painting a grim picture of unchecked power.
Not Felon, But Not Clean
Even when felony charges weren’t involved, controversy often wasn’t far behind. Take Robert DeLeo (D-Revere), Speaker from 2009 to 2020, who in 2014 was labeled as an “unindicted co-conspirator” in a case involving job trading in the state Probation Department. He left office for a university post without ever facing formal charges. While DeLeo denied wrongdoing and avoided any legal fallout, the episode added another layer of controversy to the Speakership’s long history.
Enter Mariano
Now, the role belongs to Speaker Ronald Mariano (D-Quincy), who took the reins in 2020. And while past Speakers have often made headlines for the wrong reasons, Mariano’s tenure has been marked by steady leadership and legislative wins.
Despite rumors that Mariano might step aside due to his advanced age (he’d be nearly 80 by Election Day 2026) his office has firmly shut down those whispers. Numerous speculations on Beacon hill have widely regarded House Ways and Means Chairman Aaron Michlewitz (D-Boston) as Mariano’s successor in waiting. Mariano’s office has confirmed he will seek a 19th term representing Quincy’s 3rd Norfolk District in 2026, and intends to run again for Speaker in 2027.
At InstaTrac, we’ll continue keeping you in the loop on all leadership dynamics. When it comes to Beacon Hill, there’s always more than meets the eye. Stay informed—and if you ever need help, don’t hesitate to reach out to us at info@instatrac.com.
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