Stephen Buoniconti’s upper lip tightened, his smile faded, his eyes glowered. Just moments before, he’d seemed like his usual upbeat, friendly but formal self; now his face was fixed in a mask of suppressed frustration bordering on rage.

If you’ve been following Buoniconti’s race for Hampden County District Attorney, watching the West Springfield Democrat’s debates against his insurgent independent challenger Mark Mastroianni or reading campaign coverage in the local daily newspaper, you’ve seen this look on his face with increasing frequency over the last month or so.

It is the look captured in a Don Treeger photograph of Buoniconti published in the Oct. 11 Springfield Republican, accompanied by an article by staff reporter Buffy Spencer titled “Hampden DA candidate Stephen Buoniconti acknowledges work as defense lawyer.”

It is the look that appears on his face in a videotaped interview of Buoniconti, a three-term state senator, by the Republican editorial board. That video, posted at Masslive.com, the Republican’s online outlet, focuses principally on Buoniconti’s continuing refusal to release his recent tax returns.

When that look first appeared on Buoniconti’s face during an Oct. 7 interview with the Advocate, he was addressing the notion of guilt by association—specifically, what he viewed as unfair coverage by the Republican in its effort to link him to defense attorney Daniel D. Kelly, a former Springfield city councilor who has represented a number of reputed organized crime figures. Buoniconti objected to the Republican’s repeated assertion that he is in a partnership with Kelly and defense attorney Peter Murphy, who has also represented defendants in mob-related cases. Buoniconti said he shares the same office suite at 115 State St. in Springfield with Kelly and Murphy, but keeps his law practice separate.

“We’re not partners,” Buoniconti said. He acknowledged that he considers Dan Kelly a good friend, but insisted that they don’t have a professional relationship. Referring to the fact that his opponent shares office space with Vincent A. Bongiorni, a highly successful trial lawyer who has represented many reputed mobsters and other notorious clients, Buoniconti said, “You don’t see that on the front page of the newspaper, do you?”

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While there may be some merit in Buoniconti’s suggestion of a double standard on the part of the Republican, any harm done by the revelation of his association with Kelly and Murphy appears to have been self-inflicted, at least in part. In debates, Buoniconti has repeatedly raised questions about his opponent’s suitability for the job of DA, based not on a critique of Mastroianni’s abilities as a trial lawyer, but on the way he has applied his talents for the last 15 years.

“There’s a big difference between us,” Buoniconti said in an Oct. 4 debate at Western New England College School of Law (his alma mater). “The last 15 years as both a prosecutor and as an elected official, I continued to fight for you, the citizens, the good citizens of the county [while] my opponent has chosen a different path. He tried to get people out early, represented the most notorious gangsters and criminals. And it’s his choice and I respect that. But to be able to do that and turn on a dime and all of a sudden become the chief law enforcement officer is something I can’t understand and put my head around.”

While that rhetorical frame—indicting Mastroianni for being a successful criminal defense lawyer and suggesting that he’ll go soft on criminals as DA—may ultimately work for Buoniconti, the strategy seems to have backfired so far, putting a spotlight on Buoniconti’s spotty legal career, which includes a small amount of criminal defense work, and his association with lawyers who happen to have some notorious clients.

Buoniconti’s relationship with Kelly and Murphy is only one of several issues that the local daily newspaper has, in the candidate’s view, reported inaccurately and unfairly, injecting into the race, he insists, “intentionally confusing questions about my candidacy.”

Since late summer, a few weeks before the Sept. 14 Democratic primary saw him handily top a field of five candidates, Buoniconti has come under increasingly pointed criticism for his failure to disclose $114,000 he earned doing legal work for the Hampden County retirement board, an issue brought to light by Republican reporter Jack Flynn. Buoniconti repeatedly defended his apparent lapse, saying that he received a “verbal” advisory from the state Ethics Commission that he was not required to report his income from the retirement board: “I wasn’t an employee [of the retirement board]. I was an independent contractor. If you read [the Commission’s financial disclosure form], it’s pretty confusing, the wording is ambiguous.”

Despite his insistence that he’s always conducted his public affairs with integrity and a commitment to transparency, Buoniconti has found himself on the defensive throughout September and October. First his primary opponents, then Mastroianni and his supporters, have exploited the ethics issue. One of his primary opponents, Hampden County Assistant DA James Goodhines, called for Buoniconti to drop out of the race following the Republican’s revelations about his retirement board earnings, while another primary opponent, Stephen Spelman, also a prosecutor in Hampden County, pressed Buoniconti to release his state and federal tax returns. Mastroianni, a longtime Democrat who sidestepped the primary to run as an independent, released his tax returns for the last three years and questioned Buoniconti’s reluctance to do the same. Buoniconti released a one-page summary of his tax filings signed by his certified public accountant, Nicholas LaPier of West Springfield.

“I’ve disclosed more financial information than Mitt Romney did in his presidential campaign,” Buoniconti told the Advocate on Oct. 7. “I’ve released all I’m going to release. I’m concerned about my family and the issue of identity theft. I’ve provided the information—what I reported for income and what I paid in taxes—while protecting my family.”

His failure to release his tax returns, as well as his refusal to answer questions about the amount he paid in taxes, however, was still haunting Buoniconti as the Advocate went to press this week. On Oct. 25, the Springfield Republican, a newspaper that endorsed Buoniconti just two months earlier in the Democratic Primary, flipped its support to Mastroianni heading into the general election. The newspaper’s editorial was surprisingly pointed in its criticism of a candidate it had supported throughout a decade of state legislative races: “Although the Republican backed him in the Democratic primary against four opponents, questions that have arisen about his openness are troubling. His refusal to release his tax return or to explain why he paid so little income tax on his earnings is disappointing. And we just don’t accept his explanation that he was worried about identity theft.”

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Throughout the spring and into the dog days of summer, Buoniconti appeared to be the likely successor to Hampden County DA William M. Bennett, who was first elected in 1990. With the most recognizable name and the biggest war chest in the race—Buoniconti reportedly came into the DA race with more than $200,000 in his campaign coffers—he seemed to survive the bumping and bruising of the summer’s primary fight against four lesser known opponents, gaining the endorsement of Springfield’s daily newspaper and going on to win his party’s nomination.

For those who’ve watched Buoniconti’s rise from the West Springfield School Committee to the state House of Representatives and then to the state Senate over the last decade, it was easy to imagine still another in an unbroken series of electoral victories for the ambitious yet carefully measured young politician.

In 2000, Buoniconti, fresh off a stint as a prosecutor under DA Bennett, defeated Walt DeFilippi, a popular and entrenched Republican state rep in the 6th Hampden District. His victory was based at least as much on hard work—Buoniconti spent months knocking on doors in the district, engaging in a retail style of campaigning that the incumbent hadn’t had to bother with in decades—as it was in persuasive rhetoric and novel ideas.

Once on Beacon Hill, Buoniconti showed a knack for keeping himself in the news, and therefore appearing ever relevant, without courting controversy or getting caught up in scandal.

Library and electronic records searches for Buoniconti’s press throughout the last decade yield a mountain of publicity, none of it amounting to more than a molehill of bad or even memorable media exposure. For the most part, Buoniconti appeared to be a yeoman lawmaker, ready to weigh in on anything from casino gambling (he supports it) to changes in the state auto insurance system (he filed a bill to protect the rights of drivers to appeal the decisions of insurance companies), often sponsoring legislation aimed at directing state resources to his district but never grandstanding, never overtly engaged in power politics.

Buoniconti told the Advocate that his approach to politics has long reflected the values he gained growing up in West Springfield as the son of an independent business owner. “I value independence—I don’t like being told what to do or how to do it—and at the same time, I value loyalty. Those values shape my approach to the job [of legislator],” Buoniconti said. “There’s a balance between [the impulse to go] off on my own and my sense of loyalty to my constituents, my colleagues, my party and the traditions of the Legislature.”

The constant need to keep that balance through a decade on Beacon Hill, Buoniconti said, is part of the reason he’s now running for DA. “There are times [in the Legislature] that you just can’t say everything you’d like to say,” he said. “It’s politics.” Being DA, he said, would allow him to have a more direct and immediate impact on the lives of people in Hampden County.

To a great degree, however, the vision Buoniconti offers for the office he now seeks seems as measured—some might say as muted—as his work on Beacon Hill. Though he is largely positive in his assessment of Bennett’s tenure, he also says that the DA’s office needs to be more closely involved in the community. “I will reach out to build partnerships with community groups and hold forums to hear residents’ concerns and empower them with the information they need to prevent crime,” Buoniconti said.

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While not the sexiest public policy ever proffered, Buoniconti’s outreach plank is part of a platform that seems tailored to his particular background, one in which his political experience rises above his experience in the courtroom. While Buoniconti has won support for his idea to open the DA’s office to greater community input from the sheriff (and kingmaker) of Hampden County, Michael Ashe, he has also invited further criticism from Mastroianni, who says that Buoniconti doesn’t have the requisite qualifications for the job of DA, so he’s rewritten the job description “to match his qualifications.”

Whether or not Buoniconti expected it when he decided to give up his chances for reelection to the senate and take a run for DA, he now faces a candidate who seems to come straight out of any one of a number of TV crime dramas like Law and Order, a lawyer’s lawyer who can rattle off intriguing bits about jurisdiction in a murder case one minute and describe a particular pattern of blood splatter the next. Against Mastroianni, Buoniconti has been forced into the role of politician vying against a top-notch lawyer—a guy who’s never lost a murder case, either as a prosecutor or as defense counsel—for the job of top cop.

Buoniconti said he finds Mastroianni’s use of the word politician in the context of this campaign “insulting and toxic. It’s always used as a pejorative.” How, Buoniconti wondered, does Mastroianni hope to attract people to public service if he’s always casting politics in its most negative light?

Unfortunately for Buoniconti, he has had a hard time keeping a positive light on his campaign for DA. Even before his primary opponents began attacking him for his failure to disclose his part-time job with the retirement board and, later, his tax returns, Buoniconti came under scrutiny in a May 23 Boston Globe investigative report on the state Probation Department—”an organization that functions more like a private employment agency for the well connected,” the Globe reported. The Globe piece singled out State Rep. Thomas M. Petrolati (D-Ludlow) as the single greatest beneficiary of campaign donations in exchange for jobs, referring to him as the “king of patronage,” but also reported an incident involving Buoniconti and a probation department employee named Michael J. LeCours. After receiving a public rebuke from a judge for writing a recommendation for Carmine Manzi, a convicted racketeer, LeCours began “donating heavily to Petrolati and state Senator Stephen J. Buoniconti,” the Globe reported. LeCours was promoted to supervisor and his annual pay increased by $20,000 a year during the same period in which he gave Petrolati $1,775 and Buoniconti $1,800, according to the Globe.

Buoniconti told the Advocate that LeCours is a friend who has donated to his campaign, but that there is no connection between LeCours’ donations and his job in the probation department.

With only a few days left before the Nov. 2 election, it appears unlikely that Buoniconti can break free of the bad press he’s attracted in this campaign—the first really bad press of his career. The combination of Buoniconti’s dubious critique of his opponent’s stellar career as a criminal defense attorney, his failure to disclose his side job as a lawyer for the retirement board, and the subsequent dust-up over his tax returns appear to have him hemmed in, limiting his ability to make a case for himself as either an experienced lawyer or an impeccably ethical lawmaker.

In attacking Mastroianni, Buoniconti has had to play down his own experience as a lawyer: his work as a state senator allows little time for his legal practice, he told the Advocate, adding that he was advised earlier in his career to “keep a hand in the law, because you never know what can happen in politics.”

Now, with his political future in doubt for the first time in his career, Buoniconti must hope that the campaign money and name recognition he gained as a lawmaker will see him through one more race.