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Dianne Wilkerson left Beacon Hill under a cloud of disgrace. Now, she’s asking voters for another shot.

Former Boston state senator Dianne Wilkerson plans to run for her old Senate seat, despite her conviction 12 years ago on federal corruption charges.Craig F. Walker/Globe Staff

It can be a tricky thing, turning one’s most glaring political weakness into a strength, but Dianne Wilkerson is giving it a shot.

Wilkerson left the state Senate more than a decade ago under the cloud of wrongdoing that led to a federal prison sentence and dealt what many thought would be a death blow to a once promising political career. Now, years after she was caught slipping cash into her bra as part of an explosive bribery scandal, she wants voters of the Second Suffolk state senate district to send her to Beacon Hill again.

Wilkerson was in full campaign mode on a recent morning, seated in a basement radio studio in Dorchester, giving her first public interview of the race to host Paul Parara, also known as Notorious VOG. Among her first tasks? Addressing the, well, obvious.


“My pitch is what happened, happened. I own that,” she told The Boston Globe after her radio appearance.

The “what” would be Wilkerson serving 2 ½ years in federal prison after pleading guilty to eight counts of attempted extortion for taking $23,500 in bribes. It was not her first transgression during her time in public office. She served six months of home confinement for tax evasion in the 1990s, followed by 30 days in a halfway house for violating the terms of the sentence. She also paid significant fines for campaign violations on two separate occasions, before her indictment on bribery charges in 2008 and conviction three years later.

From those lemons comes Wilkerson’s attempt at campaign lemonade in a state Senate district that covers several Boston neighborhoods, including Dorchester, Mattapan, Jamaica Plain, and the heart of Roxbury. She said she is deeply aware of the pain she caused her family and the community that she loves. But she also argued the district’s voters won’t hold those mistakes against her, pointing out that a high percentage of Black men in Boston have been court-involved at one point or another in their lives. (More than 40 percent of the state Senate district’s population is Black, according to state figures.)


“You can’t scare someone away by telling them, ‘You know she has a CORI,’” she said, referencing the state’s criminal offender record information system. “Because that’s their family. That’s their mother, that’s their father, that’s their sister. That is our reality.”

“I don’t have any secrets in the closet,” she said. “My clothes are hanging in the middle of Blue Hill Avenue for everyone to see.”

She batted away the notion, raised by critics, that she doesn’t appear remorseful. “That’s not the stock I come from,” she said. “We don’t walk bent over; you pick up and you keep moving.”

During the two-hour plus radio interview earlier this month, Wilkerson spoke in a direct and straightforward manner, revealing glimpses of the political talent that years ago had gadflies speculating about how high Wilkerson’s ceiling might be: Mayor? Congress? She talked about the wealth gap between white and Black Bostonians. She lamented inequities in the state’s procurement process and offered numbers to back up her criticisms. She highlighted infrastructure shortcomings at Boston’s public schools, and rapped Governor Charlie Baker for lack of diversity in his Cabinet. Obliquely, she faulted her rivals for the state senate seat — three others have announced they are running so far — for not having as much experience as she does.


She appeared relaxed. When asked how old she is, she joked, “Old enough to run for office.” (She is 67.) She faced questions about her past high-profile misdeeds calmly. “Anytime, anywhere people want to ask questions, I’m ready to answer them,” she said.

She plans to launch a website soon and said she has reached an agreement with someone to be her campaign manager but is not ready to announce who it is yet. She said she has already done some polling in the district.

So far, her campaign opponents have held their fire. State Representative Nika C. Elugardo, who launched her campaign for the seat in December, said Wilkerson “certainly has a right to run for this seat,” adding that “I am excited to have her in the race.” The Rev. Miniard Culpepper, a senior pastor at Pleasant Hill Missionary Baptist Church in Dorchester, who is also running, thinks voters will be looking for “a new voice.” Attempts to reach another contender, State Representative Liz Miranda, were not successful.

Joyce Ferriabough Bolling, a local political consultant who has done work for Wilkerson, said “she has a spectacular record” and city residents know her for contributions large and small, including acts of kindness like paying for the funerals of gunshot victims.

“She’s the first one to help,” said Ferriabough Bolling during a recent phone interview.

Ferriabough Bolling said people can learn lessons from past missteps and everyone deserves a second chance.


“You know how many people have CORIs here?” she asked, echoing Wilkerson’s own talking point. “Folks don’t want a whole talk about what you’re going to do as much as want to assess you by what you have done.”

For Wilkerson, the accomplishments are substantial. She first came to prominence in the 1980s as the legal counsel for the Boston branch of the NAACP. In that post, she negotiated a landmark consent decree with the Boston Housing Authority, and won widespread praise as a forceful advocate and tough negotiator. She also took a high-profile role in attacking banks for discriminating against people of color in lending practices and seizing property from homeowners of color who had been encouraged to take out bogus second mortgages. In 1992, she became the first Black woman to be elected to the Massachusetts state senate, defeating incumbent Bill Owens in the process. Wilkerson, who lives in Roxbury, held that post for 15 years.

Darnell Williams has known Wilkerson since they were students together at American International College in Springfield. He used to baby-sit her children while she was at class. Now a Roxbury resident, Williams summed up the community divide on Wilkerson: she still has her fans locally, but there are also those who “wish she would go quietly into the night.”

“It is a trust factor, a question of whether we’ll have a repeat performance of [past behavior] or if there’s been a change in character,” said Williams, the former head of the Urban League of Eastern Massachusetts, over the phone recently. “That’s a tough sell.”


That dichotomy of public opinion regarding Wilkerson was on display recently in Roxbury’s Nubian Square.

Michelle Battle-Darby, a Dorchester resident who was waiting for a bus, said everyone makes mistakes and that if Wilkerson is able to run, she should do it.

“She has to make sure if she goes in there, she cleans up her act,” said Battle-Darby. “I hope she learned her lesson. I remember her; she did a lot of good work.”

Others wondered why Wilkerson would subject herself to the rigors and scrutiny of a political campaign, given her past transgressions.

“Why would she do that to herself?” asked Tarnisha Dotton.

Barber Eric Walker took a break from his work to give his take: Wilkerson broke the community’s trust and he would not be voting for her. “She’s getting a ‘hell no’ from me.”

Inside another barber shop, Kathy Kim, owner of Alpha & Omega, one of the oldest mom-and-pop sneaker stores in Boston, thought it was time for a “new generation to step up.”

“I’m not disrespecting her. She did a lot of good work for her community. She did her time and she’s picked herself up,” said Kim. “[But] it’s time to pass on the baton to the younger generation.”

But when presented with a question about whether it is time for a new generation to lead, Wilkerson dismissed the premise as racist, asserting elderly white lawmakers don’t face such skepticism.

“That’s only an argument that you guys use for Black people,” she said.

The rogues’ gallery of Massachusetts politicians is extensive. After all, Boston is a town that produced James Michael Curley, a politician dubbed the Rascal King who remained enduringly popular despite being sent to prison twice — once in 1904, after taking the civil service exam for a constituent who wanted a job at the postal service, and then again in 1947, during his final term as mayor, when he was convicted of mail fraud. More recently, the Legislature went through a string of three straight House speakers who all left under a legal and ethical cloud.

For her part, Wilkerson said she is running to win. She threw cold water on any latter-day-Curley analogies. She said that post-incarceration, she has not hidden from public view, saying she meets with some city councilors regularly.

But the chief question remains: Can voters trust her?

“They’ll have to decide that,” she said. “That’s their decision.”

Jeremiah Manion, Adrian Walker, and Matt Stout of Globe staff contributed to this report.

Danny McDonald can be reached at daniel.mcdonald@globe.com. Follow him on Twitter @Danny__McDonald.