Analysis: Getting to ‘yes’ at City Hall can be a perilous journey

In January, 1980, Kevin White began his fourth and last term as mayor with an inauguration at the Strand Theatre in Dorchester’s Uphams Corner. To have the setting outside Boston’s downtown areas was unusual, and it helped dramatize the mayor’s message: that urban revival was not only possible beyond the Quincy Market and the South End, but that it would be his priority.

The revival didn’t begin with White. There were grassroots efforts on several fronts in Dorchester with community health centers, community development corporations, home repair organizations, and neighborhood leaders trying to preserve the Strand. Less than a year earlier, Dorchester buildings had gotten high-profile make-overs, whether in the first installment of “This Old House” appearing nationally on public television, or in the redevelopment of the Baker Chocolate mills buildings. These were proof that something old and even left vacant could still exert market appeal, especially with help from government programs.

White’s administration would soon apply that logic in Uphams Corner to the Pierce Building, one of two landmark structures at the intersection of Columbia Road and Dudley Street. But, within less than two years, the journey from a widely hailed vision to reality would be derailed by actions resulting in a federal charge of attempted extortion against a city employee who was one of White’s political operatives.

Other than involving $50,000 from a developer seeking an approval from the city, the case has little in common with the bribery charge against a former city worker announced by federal prosecutors on Aug. 30 of this year. But both cases show at least a stubborn perception that the city’s development process can be swayed by money and connection—beyond the legal channels of campaign finance, and even possibly without knowledge or consent of elected officials.

A four-story structure with retail and office space, the Pierce Building dated from 1910. Though the ground floor had a health and beauty aids store operated by the Rix chain, the building had been taken by the city for unpaid taxes. That meant the city could sell the property to a designated developer whose costs could also be reduced by a low-interest loan or even the terms of sale.

But Kevin White’s commitment to neighborhood revitalization overlapped with methods that, during his last two terms, observers likened to a political machine. With the conversion of community development aid from the federal government into block grants—instead of categorical funding—there was more power over spending in the hands of mayors. In declining neighborhoods with declining business centers, the funds could be one more tool for making improvements—or accumulating political support.

Political support can mean approval from voters, but it can also mean campaign donations. By early 1981, it was only a short step from there to a who’s who of campaign donors chipping in to a birthday party for the mayor’s wife Kathryn. Planned to be held at the Museum of Fine Arts, the party was called off after news of it had created widespread furor.

Almost a decade later, White admitted publicly that the event was meant to help with family expenses. But that was after federal charges had been terminated short of sustainable convictions. And there was no indication that White himself was involved in the event’s organization.


At the time, neighborhood leaders in Uphams Corner and Columbia-Savin Hill were more focused on the mayor’s chief local operative, known at local meetings as Jack Williams. After trying his hand at running a sub shop, Williams volunteered for White’s 1979 re-election campaign and afterward got a job with a new offshoot of government, the Neighborhood Development Agency (NDA). From there, he went on to become the Uphams Corner Little City Hall manager before switching to another position within the administration.

Even compared with other Little City Hall managers, Williams wasn’t shy about advertising his allegiance to his boss. There were indications that he could help fast-track a license for a business, and there was the story of how he tried to mobilize a turnout that fell two votes short of ousting a leader of the Columbia-Savin Hill Civic Association.

Even at routine public meetings on block grant spending, Williams could be seen securing a photo of White to a podium with multiple strips of masking tape. It was a painstaking display of showing who was in charge—and, arguably, who was being served by Jack Williams. By the end of 1981, that relationship was put into question under a harsh spotlight when federal prosecutors accused Williams of attempted extortion from a would-be developer of the Pierce Building.


In October of 1981, when neighborhood leaders scrambled on short notice for a presentation of plans for redeveloping the Pierce Building, they might already have expected an effort to skew the designation process. Also competing for the designation were two other developers, including the owner of the Rix chain. What the leaders didn’t expect was a plan from a developer who wore flashy jewelry and drove around in a Lincoln Continental.

As it turned out, the developer at the meeting, who went by the name of Anthony D’Alesandro, had a plan that supposedly went beyond the Pierce Building to include the neighboring property on Columbia Road, famed locally as the site of the world’s first supermarket. The “Uphams Market” building was owned by a non-profit, with the second floor used at the time by a church congregation. D’Alesandro had a purchase and sale agreement to buy the property for $125,000, and he had an idea for the second floor – a “buckaroo steakhouse.”

Neighborhood groups were not impressed, and four of them made it known they preferred the plan from the Rix Corporation. Then, in late November, Williams was charged with attempting to extort $50,000 from D’Alesandro. A transplant to Boston after entering a federal witness protection program, D’Alesandro had been recording his conversations with Williams for the FBI. Within a matter of months, Williams was sentenced to three years in prison.

According to contemporary reports in The Boston Globe, some city officials had doubts about D’Alesandro’s proposal, and about the other plans, too. Under White’s successor, Ray Flynn, the Pierce Building was turned over to the nonprofit Dorchester Bay Economic Corporation, which has recently undertaken new renovations.

Based on information publicly available in 1981, D’Alesandro seemed an unlikely candidate for what he described as a $3 million project. His earlier property dealings in Dorchester had been mainly at the bottom of the housing market. Aside from a three-decker where he reportedly lived, there were a number of short-term transactions, often for a nominal price plus assumption of back taxes and fees. Some of the transactions were with figures under the watch of arson investigators, but the Boston Fire Dept. never linked D’Alesandro to any criminal activity. “I understood everyone’s concern at one point that I might have been another straw,” D’Alesandro later told a Globe reporter. “I didn’t even know what a straw was at the time.”

White reportedly was surprised by the federal charges, but he defended his earlier decision to make Williams a part of his administration – because Williams was someone he liked.


Fast forward to 2019, with another former city official involved with a developer scheduled to plead guilty to taking a bribe of $50,000, for supposedly influencing a decision by the Zoning Board of Appeal.

The official, John M. Lynch, had served under multiple administrations, and there’s little sign of his clashing with neighborhood groups or his visibility as a political operative. It could be that Lynch and Williams have almost nothing in common, other than being city officials from Dorchester. But the bribery case against Lynch could be seen as one more example of a developer expecting a city decision to hinge on payoff, even if for a project with a lower profile and the kind of request that, by some accounts, is routinely granted.

These days, regulatory approval by the city mainly unlocks benefits from a tight housing market. And, with a few taps or clicks, it’s possible to get more public information about proposed developments, large or small. But this new federal charge shows that a critical decision can still be made about a development without public accounting—unless there’s a criminal investigation.

A tight real estate market means more opportunities to make money, to increase jobs in the building trades, and to swell the tax base. There are also mounting pressures to ease the market forces driving up rents and causing many people to leave the city. And, for those who can afford to stay, the market relief from added supply can mean new shortages when it comes to things like parking. Taken together, those factors can make decisions about development highly conflicted.

What hasn’t changed is the cross-section of fields represented on the Board of Appeal. They have the benefit of knowledge about development, but also a broad (if not legally conflicting) interest in increasing supply. And there are still complaints from the neighborhoods, whether about the lack of locally affordable housing or about suggestions to improve plans that seem to go unheeded.

Neighborhood leaders often complain that Boston’s development process concentrates too much control in its mayors, business leaders, and campaign contributors. But, when the process results in federal charges, it can also turn out that there’s a shortage of oversight, whether from outside an administration or even from within.

If Kevin White was truly blindsided by what happened with the Pierce Building, that was not the case with Anthony D’Alesandro. His agreement to buy the adjacent “Uphams Market” building, filed almost three months before the presentation to neighborhood leaders, could have been withdrawn if he failed to secure approval for the “S.B. Pearce Building” (sic), or extended if there were a delay. “Buyer shall act in all due haste to prevent this”, the agreement stipulated, “but the seller recognizes a possible occurance (sic) through no fault of the buyer.”

Chris Lovett is a veteran Boston journalist who covered Dorchester in the 1970s and 80s for the Dorchester Argus-Citizen. Lovett is anchor and news director of BNN-TV's Neighborhood Network News and a frequent contributor to the Dorchester Reporter.