The Perfect Enemy | A second chance for Dianne Wilkerson? Think twice about it. - The Boston Globe
May 27, 2022

A second chance for Dianne Wilkerson? Think twice about it. – The Boston Globe

A second chance for Dianne Wilkerson? Think twice about it.  The Boston Globe

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Should Dianne Wilkerson run for her old Senate seat, despite her conviction 12 years ago on federal corruption charges? That decision is up to her.

It will be up to voters to decide if she deserves a second chance — and they should think twice about it. That’s what Wilkerson’s would-be rivals are saying, if ever so diplomatically.

State Representative Nika Elugardo told me Wilkerson previously encouraged her to run for her old seat and said she looked forward to being represented by her. Now that Wilkerson has pulled nomination papers for her own potential candidacy, what does Elugardo think about the prospect of running against someone with Wilkerson’s criminal history?

“It’s not something I would hold against her as far as getting in,” she said. “But it’s data I would take into account: What is your pattern and practice for how you do business?”

Noted state Representative Liz Miranda, “I welcome Dianne warmly to the race. . . . I respect much of what she’s done.” But asked specifically what she thinks about Wilkerson’s bid to write a new political chapter for herself, Miranda said: “Folks deserve redemption. But there’s a clear difference between those currently in the race and those who are thinking about jumping in.”

Echoed the Rev. Miniard Culpepper, who is also running for the seat, “Everyone has a right to run. Welcome, Dianne to the race . . . but when I think about what I’ve done . . . I have the most experience.”

Leave it to a former politician to address the political elephant in the room more bluntly. Jeffrey Sanchez, who served in the Legislature at the same time as Wilkerson, said her legal troubles back then cast a shadow on all Beacon Hill politicians. Voters were asking, “Could they trust me as a politician? It was not cool. It gave a bad name to being an elected official,” said Sanchez, who now works as a senior adviser at Rasky Partners. He lost his seat to Elugardo, who was seen as more progressive, and is not aligned with any candidate.

With help from the media, Wilkerson is clearly trying to put her past behind her. A recent, lengthy Boston magazine piece entitled “Who is Dianne Wilkerson?” is a prime example. It covered the highs of her career – she was the first Black woman elected to the state Senate, in 1992, and was seen as a political superstar and even a potential mayor — and gave her a chance to address the lowest of the lows: the infamous 2008 photo of her stuffing cash into her bra. That scandal led to her resignation from the Senate, a guilty plea for taking $23,500 in bribes for using influence to help someone get a liquor license, and 30 months in federal prison.

Since her release from prison, she has been involved in assorted community causes that raised her profile and helped her rebrand herself. For example, Boston magazine recently put her at number 82 on the list of the 100 most influential Bostonians. Her criminal history was not mentioned — just her dedication to fighting for racial equality and social justice, her efforts to help register voters for US Senate races, and her demand for more equity in testing and vaccine distribution during the COVID-19 pandemic. Former House speaker Sal DiMasi, who was also convicted of federal corruption charges, could only dream about that kind of miraculous political resurrection.

Then again, Massachusetts is the land of James Michael Curley, who was twice convicted of criminal conduct and still managed to win assorted elections as mayor, governor, and congressman. Before her federal extortion conviction, Wilkerson also pleaded guilty to failing to pay $51,000 in federal income taxes, a prosecution she described to WBUR reporter Phillip Martin as “selective.” In 2010, she pleaded guilty to attempted extortion, stemming from the bra-stuffing incident; she told Martin and Boston magazine writer Catherine Elton she was set up by the FBI. When Elton asked if there’s anything she would have done differently, Wilkerson said, “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 also said she pleaded guilty because she believed if she took the case to trial, a predominately white jury would convict her and she would receive a longer sentence.

Some voters will accept that. But they should not be so ready to let her rewrite history, or erase it, without fully addressing it.


Joan Vennochi can be reached at joan.vennochi@globe.com. Follow her on Twitter @joan_vennochi.