Adrian Walker

Onetime rising star falls hard

By Adrian Walker
Globe Columnist / June 4, 2010

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Clad in a cream-colored suit and yellow blouse, Dianne Wilkerson stared straight ahead and softly acknowledged her guilt over and over yesterday, as prosecutors described her crimes.

The end came quietly, belying one of the most stunning declines in the history of Massachusetts politics. It was a day that her supporters said would never come; just last week, her attorney had said she would go to trial.

An hour after Wilkerson’s plea, her lawyer, Max D. Stern, explained her sudden conversion.

“Clearly, the trial was about to start, and she had to decide whether she was going to fight it out or take responsibility for what had happened and what she had done,’’ Stern said. “She’s been in this terrible purgatory since she was arrested, and this is the first step in getting out of that purgatory.’’

The depth of the fall is hard to appreciate without looking back at the rise. In 1992 — fresh off high-profile legal victories representing the Boston NAACP — Wilkerson ran for the state Senate against incumbent Bill Owens. Owens was a decent and dignified public servant, but theirs quickly became a clash of Old Guard vs. The Future, which was no contest.

She cleaned his clock. In a city whose politics were showing signs of moving past a century of Irish dominance, she was mentioned as mayor material.

Even before there were crimes, there were missteps, as when she predicted that she would decide the 1993 mayor’s race because she “controlled’’ 27,000 votes, approximately the total she had garnered in her victory. Her preferred candidate, James T. Brett, lost by plenty, proving the weakness of endorsements, but Wilkerson’s hubris could be forgiven as the flip side of her boldness.

Not so easily spun was the tax case. Wilkerson was indicted in 1997 and eventually pleaded guilty to failing to file her taxes for two years in the mid-1990s. That debacle brought her ascent to a screeching and permanent halt.

Nothing was ever the same after that. The tax debacle was followed by a seemingly unending series of missteps. Not only the mayor’s office, but a chance at Congress or even the Senate presidency all slipped from her grasp.

Still, she won reelection repeatedly, thanks to a forgiving constituency convinced that she felt its pain. In the context of her official duties, she was terrific, and if she could compartmentalize, so could her voters.

She was an early champion of domestic partnerships, and later gay marriage, and an outspoken and effective foe of racial profiling. She was an eloquent voice on behalf of gay marriage as a civil rights issue, even though many of her supporters strongly disagreed. Wilkerson is a punch line only to people who don’t know her or her work.

But the distinction supporters had always drawn between professional competence and personal messiness came crashing down when she was caught on tape taking bribes from a Roxbury businessman who wanted a liquor licence. She could help him, she said; she believed in doing good and making good.

There she was on video, stuffing the money down her bra, and even her truest believers could no longer say that she would never sell out her office.

Boston is no stranger to political scandals, but the affair will be remembered for its sheer brazenness, the images of money changing hands in the shadow of the State House, as if it were business as usual. That, and the fact that a career has been thrown away for a grand total of $23,500.

Wilkerson was remarkably composed during the brief hearing yesterday. Surrounded by friends, clergy, and some former staff members, she displayed relatively little emotion as she walked past a group of reporters outside the courthouse, leaving all to wonder what she must really be feeling.

“It’s a very stressful day and a very painful day,’’ said her pastor, the Rev. John M. Borders III of Morning Star Baptist Church. “But I’ve seen tremendous growth from her spiritually in the past two years.’’

Perhaps, as Stern suggests, there is relief in ending the uncertainty. Under the plea agreement, prosecutors will seek a four-year sentence, not short, certainly, but decades less than she could be facing.

“On the one hand, I think she’s pretty low, but on the other hand, I think she’s made a decision to face this and it’s time to move past this,’’ he said. “She wants to take responsibility and take her punishment and move on to the rest of her life. In that sense, that’s a positive.’’

The dream Wilkerson once embodied — of power wielded by a different race and gender — died years ago. She has come to represent something else altogether, a return to old-school corruption.

Decades ago, Bostonians would have been unconcerned about a few thousand dollars changing hands in an envelope. That is no longer true, a fact that was on painful display yesterday.

Adrian Walker is a Globe columnist. He can be reached at

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