For Wilkerson, a looming question of culpability

Roxbury pol eyes comeback 12 years after conviction on corruption charges

TENACITY ALONE SOMETIMES brings its own rewards, and Dianne Wilkerson certainly looks determined to complete her return from the political wilderness more than a decade after being sent off to federal prison for abusing the power of her elected office. 

Some may call it more a matter of chutzpah.

A one-time rock star on the political landscape, the former Roxbury pol became the first Black woman elected to the state Senate in 1992 before a long fall that included various tax and campaign finance charges and ended with a bang – a felony extortion conviction that sent her to federal prison in Connecticut for two and a half years.

But more than a decade after her once promising political career came crashing down, Wilkerson appears poised to mount a comeback attempt. On Friday, she pulled nomination papers to seek her former Senate seat. It’s an open-seat contest with Sonia Chang-Diaz, who defeated Wilkerson in a Democratic primary 14 years ago, giving up the post to run for governor. Wilkerson declined to comment on her plans yesterday to GBH and the Boston Herald

Wilkerson had made no secret of the fact that she was considering a comeback attempt, and she has been increasingly visible on the local scene. She has been outspoken during the pandemic as a leader of the Black Boston COVID-19 Coalition. She also attempted to organize Black voters to rally around Kim Janey – who ended up placing fourth in last year’s mayoral race in Boston. 

Her entry would scramble what had been shaping up as a three-way Democratic primary for the Senate seat among state Reps. Nika Elugardo and Liz Miranda and Rev. Miniard Culpepper. 

A big question looming over a Wilkerson comeback run will be how she frames her federal corruption conviction. Wilkerson pleaded guilty to taking $23,500 in bribes to help a businessman with approvals to open a Roxbury nightclub. She was caught on surveillance video stuffing $100 bills into her bra – a shot that the Herald reminds readers of this morning by splashing it across its front page. 

Federal surveillance video in 2008 showing Dianne Wilkerson stuff cash into her bra.

Despite the now infamous photo – and her guilty plea to the charges – Wilkerson has never exactly fallen on her sword and squarely admitted wrongdoing. In a GBH story a year ago, titled “The rehabilitation of Dianne Wilkerson,” she points to being set up by the feds in a sting operation. 

When asked by GBH reporter Phillip Martin whether she regrets her actions, Wilkerson offered a curious reply. 

“I would say yes,” she said. “But I don’t know what I could have done, like I did not expect [the informant] to bring cash and I couldn’t walk down the street with it in my fist. It was out of caution as opposed to subterfuge. Like, I didn’t even have an envelope.”

But the crime wasn’t that she stuffed cash in her bra rather than discreetly in a brown envelope. 

In a lengthy profile three months ago in Boston Magazine, Wilkerson suggests the conviction was all a mistake. 

“I’m trying to go through it and I can’t think of anything I shouldn’t have done, because I know so much more about what happened,” she told writer Catherine Elton while seated at No. 9 Park, the swank restaurant in the shadow of the State House that was the scene of the famous photo. She goes on to suggest the money was all above board because she was working as a consultant for the businessman who handed her the wad of $100 bills that day. 

Meet the Author

Michael Jonas

Executive Editor, CommonWealth

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

About Michael Jonas

Michael Jonas has worked in journalism in Massachusetts since the early 1980s. Before joining the CommonWealth staff in early 2001, he was a contributing writer for the magazine for two years. His cover story in CommonWealth's Fall 1999 issue on Boston youth outreach workers was selected for a PASS (Prevention for a Safer Society) Award from the National Council on Crime and Delinquency.

Michael got his start in journalism at the Dorchester Community News, a community newspaper serving Boston's largest neighborhood, where he covered a range of urban issues. Since the late 1980s, he has been a regular contributor to the Boston Globe. For 15 years he wrote a weekly column on local politics for the Boston Sunday Globe's City Weekly section.

Michael has also worked in broadcast journalism. In 1989, he was a co-producer for "The AIDS Quarterly," a national PBS series produced by WGBH-TV in Boston, and in the early 1990s, he worked as a producer for "Our Times," a weekly magazine program on WHDH-TV (Ch. 7) in Boston.

Michael lives in Dorchester with his wife and their two daughters.

Asked why she pled guilty then, Wilkerson tells Elton she didn’t think she would be judged by enough Black jurors who would understand the role of racism in her arrest, and that she’d be convicted and face a longer sentence if she took the case to trial. 

How that account will play in the court of public opinion is now the question.