Former state Sen. Dianne Wilkerson, who resigned and went to prison after video caught her stuffing $100 bills into her bra, is mounting a comeback.
Wilkerson recently filed signatures in an effort to regain her old Senate seat in Boston. And despite her bribery conviction, several voters in her district said they are willing to give the eight-term legislator a second chance.
"It’s not like she never did anything for this community," said James Beverly, wearing a green Celtics hat, as he waited for a bus in Roxbury’s Nubian Square. "She always put this community first."
Beverly said he feels like he knows Wilkerson. He said he used to run into her on the street, and she would always stop and talk.
"It’s very rarely that we get Black representation in this community and they really represent us," Beverly said. "A lot of times people are running for Black spots in our community, and don’t really represent us."
In nearby Grove Hall, Robbie Robertson echoed the sentiment.
"She used to be at the corner of Quincy Street, down there every morning," he recalled, pointing across a Stop & Shop parking lot. "I used to go to work and I used to see her every morning."
Robertson said he hasn’t seen that same kind of representation since Wilkerson left office nearly 14 years ago.
"You have to be visible, you have to be around, you have to let people see you, otherwise, what’s the point?"
He paused before delivering the punch line: "Just sitting around on your ass getting fat?"
A Dual Challenge
But Wilkerson faces a dual challenge to regain her old Senate seat.
First, several other well known Democrats jumped into the race months before she did: Rev. Miniard Culpepper, and state Reps. Nika Elugardo and Liz Miranda. The primary is scheduled for Sept. 6.
And second, there's her criminal record. Wilkerson pleaded guilty to taking $23,500 in bribes and spent over two years in prison.
Prosecutors even released a photo of Wilkerson stuffing some of the bribe money into her bra — a photo picked up by news organizations across the country. Comedian Jay Leno cracked jokes about it on national television.
Wilkerson acknowledges that image is hard to forget.
"I don't have any secrets in my closet," she told B87 FM host Notorious VOG in her first public interview since entering the race. "I tell people my clothes are hanging in the middle of Blue Hill Avenue for everybody to see."
She said she’s willing to fight for neighborhoods like Roxbury and Dorchester as they recover from the pandemic, and from old racist policies like redlining.
"We can't afford to have people representing us whose focus is being nice and getting their colleagues to like them," she said. "That's not what this job is about."
Wilkerson declined to talk to WBUR about her campaign. But in an interview earlier this year with Boston Magazine, she denied ever taking bribes.
She argues the bribes were actually consulting fees — and insisted she only agreed to a plea deal to get out of prison faster.
Comebacks After Corruption
History shows it’s difficult for politicians to stage a comeback after being found guilty of corruption. Both Ohio Congressman James Traficant and U.S. Sen. Ted Stevens lost elections after felony convictions.
One famous exception is former Boston Mayor James Michael Curley.
Curley's first brush with the law came early in his career as a Boston Alderman, when he got caught taking a civil service test for a friend who wanted to be a mail carrier. Curley later went to jail.
Still, Curley found a way to turn the jail time to his advantage, said biographer Jack Beatty. Curley ran for re-election under the slogan, "He did it for a friend."
Curley later went to federal prison for mail fraud while serving as mayor. But he didn't resign and reclaimed his old job when he returned to Boston. A brass band welcomed him with the tune “Hail to the Chief.”
In neighboring Rhode Island, many fondly remember Vincent "Buddy" Cianci, who served 21 years as the mayor of Providence and had his own legal complications.
Voters elected him to his second term in the 1990s after he pleaded no contest to charges he kidnapped and tortured a man he thought was romantically involved with his ex-wife.
"A lot of people in the Rhode Island electorate, particularly men of a certain age, didn't see this as public corruption," said long-time Rhode Island political reporter Scott MacKay. "They thought he was, you know, in the macho realm, kind of defending his name and his honor and a lot of that foolishness."
But Cianci’s political career ended after he was convicted of corruption, and served four years in prison. After getting out of prison, Cianci eventually ran for another term as mayor but lost.
Wilkerson also had a notable career as the first Black woman ever elected to the state Senate in the '90s. But some who know her think it could be a tough road back to Beacon Hill.
Mimi Turchinetz worked as Wilkerson’s staff counsel in the State House in the '90s.
Standing outside the public library in Roxbury, she recalled Wilkerson was once the highest-ranking Black woman in state government.
"I mean it’s a shame. She could have run for [Congress] and that all blew up, and that’s too bad," she said.
Now Turchinetz thinks it’s time for new leadership.
"I like Dianne, I do. I think that she’s a competent, brilliant person," she said. "I’m not sure it’s the right race for her to be running."
Another person who was skeptical about Wilkerson’s decision to run — at least at first — was the B87 radio host, Notorious VOG.
Speaking after his morning show wrapped up from his Dorchester studio, he said Wilkerson has deep roots in the community.
"She was loved, people liked her," he said.
VOG pointed out Wilkerson is running for office in a district where many people personally know her — not just the infamous photo.
"I think she's smart enough to realize she's not going run for governor. You know, there's no Sen. Wilkerson or Congresswoman Dianne Wilkerson, Mayor Diane Wilkerson," he said. "This would be it."
He said the situation reminded him of a certain song, which he played the day he interviewed Wilkerson on air.
"That whole day, when I did the whole Dianne Wilkerson thing, I was playing some Donna Summer, 'Last Dance,' " he said. "And I kept playing it and playing it. And people kept calling and requesting it, saying, 'VOG play it again.' "
"And I said, this is true. It's become her last dance, a last chance for love."
Wilkerson certainly still has a lot of love in her old district. The question is whether that love will be enough to lead her to victory.
This story was reported with WBUR's Steve Brown.
This segment aired on June 3, 2022.