Nearly 10 years ago to the day, I wrote a column about Stephen Buoniconti, then a 31-year-old assistant district attorney in Hampden County who was running against an entrenched Republican, Walter DeFilippi, for state rep in the 6th Hampden District.

I remember getting a fair amount of feedback on the column at the time, most of it laudatory, but re-reading it today, I feel more than a little embarrassed.

I got my facts right and my overall analysis was reasonably sound. I reported that Buoniconti, who saw himself as a “conservative Democrat,” was struggling to gain support within his own party; so loyal were some Dems to DeFilippi, a popular state rep who’d helped to rally GOP support for then-House Speaker Tom Finneran (D-Mattapan), that they actually tried to pressure Buoniconti not to run.

Although I didn’t argue the point explicitly, my subtext was obvious: the fresh-faced Buoniconti represented a serious challenge to politics as usual in Hampden County and on Beacon Hill, where the General Court, with its ostensibly Democratic, even liberal tilt, was actually in the grip of retrograde tribal “Republicrats” like Finneran and former Senate President Billy Bulger—corrupt machine pols with deeply conservative impulses on social issues like gay marriage, abortion rights and capital punishment.

What makes me red-faced today isn’t so much the substance of the piece as its style, which was, in a word, gushing. I called it “About Face,” a double entendre signaling not only my hope that voters in the 6th Hampden would dislodge its entrenched incumbent, but also how impressed I was with, among other things, Buoniconti’s “good taste” in keeping his thinning hair “cropped close… like Bruce Willis and Sean Connery.” Without a lot of hair to distract you, I wrote, “you can focus on [Buoniconti’s] face, his clear, intelligent eyes, his broad, unaffected smile.” Good grief!

Many readers will know the rest of the story: Buoniconti went on to beat DeFilippi, beginning a legislative career that rarely saw him far from the center of power on Beacon Hill. As a state rep and, since 2005, a state senator, Buoniconti has been largely supportive of his party’s leadership, rising rapidly through the ranks and emerging, along with House Speaker Pro Tempore Tom Petrolati, as one of the most powerful members of the Western Mass. legislative delegation.

And while his career as a lawmaker is distinguished neither by great scandal nor memorable agenda, Buoniconti is ready for yet another career move. In November, Buoniconti faces independent candidate Mark Mastroianni in a race for Hampden County District Attorney.

On its surface, the Hampden County DA’s race turns on a dynamic similar to the one that animated the DA’s race in the Northwest District (Hampshire and Franklin counties plus Athol). In that race, effectively decided in the Sept. 14 primary, voters had a choice between a longtime prosecutor, Michael Cahillane, and a longtime pol, Hampshire County Register of Probate Dave Sullivan. Sullivan won by a 2-1 margin (and faces no opposition in November). In addition to the main narrative of the race—prosecutor versus politician—both candidates tried to paint the other as the more incumbent-like of the two. In the end, voters appeared to associate Cahillane with the real incumbent, his former boss, DA Betsy Schiebel.

Just as Cahillane asked voters to give his superior prosecutorial experience greater weight than his opponent’s superior political experience, Mastroianni, a veteran trial lawyer with ample experience as both a prosecutor and criminal defense attorney, hopes voters will see Buoniconti as a lightweight lawyer and heavyweight pol. Meanwhile, Buoniconti, a fulltime politician who only practices law as a sideline, argues that his administrative abilities, as well as his prowess on Beacon Hill, add an important dimension to a resume that includes his brief stint as an assistant DA.

A longtime registered Democrat but a newcomer to elective politics, Mastroianni chose not to compete in the Democratic primary, where Buoniconti topped a field of five. Prior to entering the race, Mastroianni withdrew his party affiliation to underscore his view that the DA’s office should be scrupulously non-partisan. Mastroianni’s gesture helps define Buoniconti as the incumbent—the guy that voters, frustrated and angry with a political establishment that keeps letting them down, should reject.

The Buoniconti I wrote about 10 years ago might not have been as innocent and idealistic as I thought he was, but he surely raised my hopes. And while I can’t say he’s broken my heart, he’s hardly lived up to my greatest expectations. If Buoniconti has some of the advantages of incumbency in this race, they come in the form of greater name recognition and a bigger campaign war chest—just what Walt DeFilippi enjoyed once upon a time.