Jerome Rappaport and the destruction of Boston’s West End

Late developer and philanthropist's legacy includes one of the most controversial project's in Boston history

Jerome Rappaport, a huge figure in Boston’s business and civic world, died on December 6 at age 94. Rappaport, a successful developer and philanthropist, had an enormous impact on Boston over a span of more than 70 years. That included his role as the principal figure in one of the most controversial development projects in modern Boston history — the razing of the working-class West End neighborhood to make way for the high-end Charles River Park housing complex. The move has been cited by critics as one of the worst examples in the country of the damage done by urban renewal efforts. Rappaport’s extensive civic and philanthropic contributions were detailed in a front-page obituary in the Boston Globe, but the West End saga, an important chapter in the city’s history and in US urban redevelopment policy, was only given a fleeting reference. Two people who played roles in Boston housing and development policy, Jim Vrabel, a former senior research associate at the Boston Redevelopment Authority, and Peter Dreier, a top housing official under Mayor Ray Flynn and now a professor at Occidental College, submitted essays sharply critical of Rappaport’s legacy from the West End project. Together with the Globe obituary, they offer a more complete picture of a central figure in recent Boston history.


By Jim Vrabel

The recent death of local developer Jerome Rappaport marks the end of the urban renewal chapter of the Boston’s development history. Unfortunately, Rappaport’s life, work, and subsequent philanthropy seem to have done nothing to persuade the city to change its approach to overseeing development over the last 70 years.

In the 1950s, as a very young man, Rappaport parlayed his relationship with Mayor John Hynes to become part of the team chosen to redevelop Boston’s West End. Critics would later brand it a “sweetheart deal.” But the problem wasn’t that Rappaport’s team (he was a junior member initially) was chosen as the developer or given a break on the price (his team was one of only three to bid on the project and paid less than $1.40 per square foot; the low bidder offered to take on the project if given the land for free).

No, the problem was that once Rapport’s team was chosen, the city allowed it to change the terms of the proposed development. The original plan called for building 2,000 new units of housing, with half affordable to the families about to lose their homes. The revised subsequent plan called for building all 2,300 units as “luxury apartments” that were out of the price range of any of the displaced West Enders.

The change from what was proposed to what was built resulted in the West End becoming what came to be seen as the worst example of urban renewal in the US – a case where an entire neighborhood made up of longtime, working-class residents living in four- and five-story walk-ups was destroyed to make way for a series of high-rise “towers in a park” inhabited by well-off newcomers.

In some ways, the city could be excused for agreeing to the change in the plan. In those days, Boston was desperate for private investment. At the time, according to the late historian Thomas O’Connor, the Boston Globe called Boston a “hopeless backwater” and “tumbled-down has-been” of a city.” In dealings, first with the Prudential Insurance Company and then in the West End, Mayor Hynes and other city officials doubtless felt the need to make  concessions to get someone – anyone – to build something – anything – in the Old Boston.

A building being razed in Boston’s West End in 1959 to make way for the neighborhood’s redevelopment into high-end housing by Jerome Rappaport. (Boston City Archives photo)

In 1960, when Ed Logue came to Boston to become director of the recently established Boston Redevelopment Authority, he took great pains to distance himself from the West End project. But in his dealings with the developers of subsequent urban renewal projects, he too felt the need to make concessions from what he and residents really wanted – to approve more demolition, more dislocation of residents, and less affordable housing – in order to get the projects built.

Backers of those concessions have since contended that they led to the dramatic transformation of what’s come to be called the “New Boston,” one of the most attractive and financially healthy cities in the US and the world today. And even today it is undeniable that Boston benefits directly from new development in the form of increased property tax payments (initially exempt from Proposition 2½ limits) and linkage “contributions” to fund the construction of affordable housing and job training – money the city can spend for what it needs and values. But by sticking with the process of promoting development over planning even once it didn’t need to do so anymore, the city of Boston has placed quantity over quality and sacrificed its ability and authority to control and guide its own future.

The Old Boston of the 1950s and early 1960s was a “buyer’s market,” where concessions to developers willing to take the risk were necessary to promote growth. Since then, though, the New Boston has become a “seller’s market,” where the city can afford to choose among developers betting on more of a sure thing. That should mean that the city doesn’t have to make concessions or just cash in on it to pay for what it really wants. It should mean that development decisions can be made to serve the city’s needs and reflect its values – from use and design to affordable housing to minority participation to climate resilience, and on and on. But for some reason, the city’s approach has not really changed in all these years. The development tail is still wagging the city dog.

In his later years, Jerome Rappaport – either out of guilt, an effort to burnish his reputation, or genuine altruism – donated millions of dollars to improve the way state and local government function. He knew that cities must grow and change. Surely even he would admit that, as Boston has changed, it should change the way it manages its growth accordingly.

Jim Vrabel is the author of A People’s History of the New Boston and a former senior research associate and editor at the Boston Redevelopment Authority.


By Peter Dreier

In 1914, John D. Rockefeller – America’s richest business tycoon – confronted a problem. On April 20, Rockefeller’s private army along with the state militia attacked a Rockefeller-owned mining camp in Ludlow, Colorado, where workers were on strike. At least 66 people were killed, including two women and 11 children who suffocated in a pit they had dug under their tent. The public blamed Rockefeller for their deaths, which became known as the Ludlow Massacre. Newspapers around the country excoriated him as a greedy robber baron. To cleanse his reputation, Rockefeller hired Ivy Lee, one of the first practitioners of the new field of public relations. Lee suggested that Rockefeller, who also owned Standard Oil, burnish his image through charity. Over several decades, Rockefeller made sizable grants to a variety of  educational, religious, and scientific organizations.

Many other business moguls followed Rockefeller’s example. Corporate titans created family foundations to divert public attention away from their business practices. Automobile tycoon Henry Ford, a blatant anti-Semite and racist who bitterly fought his workers efforts to unionize, was among the most successful at rehabilitating his image. Today, the Ford Foundation is a bastion of liberalism.

In recent years, the Sackler family – whose company, Purdue Pharma, made billions peddling the addictive painkiller OxyContin —  went on a philanthropy binge, endowing the Sackler Wing at the Metropolitan Museum of Art, the Sackler Gallery in Washington, the Sackler Museum at Harvard, and  Sackler-branded projects at the American Museum of Natural History, the Guggenheim Museum, the Smithsonian Institution, the National Gallery, the British Museum, the Louvre, and at Yale, Cornell, Oxford, Cambridge, Tufts, NYU, the Royal College of Art, Kings College London, the University of Edinburgh, and other universities. Some of those institutions have recently removed the Sackler name in the wake of lawsuits revealing that the family knowingly promoted OxyContin despite recognizing its addictive qualities that led to our current opioid crisis.

Boston real estate developer Jerome Lyle Rappaport also sought to rehabilitate his tarnished image. It appears to have worked. After Rappaport died on December 6 at 94, the Boston Globe’s obituary described him in the headline as a “philanthropist” and “civic leader.” The Harvard press office released a statement from President Lawrence Bacow who said that “Jerry worked tirelessly to improve the world by better connecting ideas and people” and praised his “dedication to public service and public policy.”  “Jerry Rappaport was a visionary leader,” proclaimed Diane Ring, Dean of the Boston College Law School. Boston’s new Mayor Michelle Wu praised Rappaport’s “commitment to public service.”

Those descriptions would be a hard pill to swallow for the thousands of residents of Boston’s former West End, who were bulldozed out of their homes to make way for Rappaport’s Charles River Park apartment complex, or the tens of thousands of Boston renters who have been displaced not by a bulldozer but by gentrification and rising rents, which Rappaport encouraged by using his political influence to weaken the city’s tenant protection laws.

Rappaport was never elected to public office but he was Boston’s ultimate power broker. He was a political insider who used his connections to enrich himself at the expense of the city’s working class residents, including the 7,000 people who were forced out of the West End in the late 1950s.

For several generations, students and practitioners have examined the West End as a case study in misguided urban planning. It is not simply a story of bureaucratic wrongdoing. It is a story about how power is wielded and misused.

After World War II, Rappaport, who was Jewish, played a key role as a bridge between the city’s Yankee business leaders and its Irish politicians.

Since the 1920s, Boston’s Brahmin business elite had written off the city. The banks and insurance companies refused to invest funds in modernizing industrial plants, in new buildings or new housing. By the end of World War II, Boston had become an economic wasteland.

Boston’s corporate elite hated Mayor James Michael Curley. He represented everything they thought was wrong with the city. It was not only that they were Republicans and he was a Democrat. Much of their hostility was a mixture of Brahmin snobbery and opposition to the New Deal-style government programs for the poor and working class that Curley supported, such as Boston City Hospital.

Curley had developed an intensely loyal following among the city’s working class. He padded the city’s budget to provide jobs for his  campaign workers and voters, and taxed  banks and businesses to pay for public works projects that employed his constituents.

But in the late 1940s, the business leaders regrouped and decided there were profits to be made after all – if they could build a new city of corporate office towers and luxury apartments. Their plans were made possible in 1949, when Congress passed a new federal program that the nation’s real estate industry had lobbied for. It was called “urban renewal.”

That year, the 21-year old Rappaport, a recent Harvard Law School graduate, joined forces with Henry Shattuck, a well-connected Republican lawyer, to organize a business-sponsored civic group, the New Boston Committee. The NBC held forums and issued reports about the need to turn Boston’s downtown into a center for retail and service businesses, corporate headquarters, and upscale housing.

Rappaport helped mobilize support in the business community and among middle-class voters for John Hynes, the city clerk, who was running for mayor against Curley. Hynes won and served as mayor for 10 years, from 1949 to 1958. Between 1952 and 1954, 10 of  Boston’s 15 city officials had been endorsed by the NBC.

Jerome Rappaport addresses the Harvard Law School Forum in 1946. Three years later he organized business leaders to help defeat Boston Mayor James Michael Curley and elect John Hynes. (Photo via Creative Commons by fdb2001)

The NBC catalyzed Boston’s business leaders to become better organized, inspiring the creation of  the Greater Boston Economic Study Committee and the Coordinating Committee (14 corporate leaders who were soon nicknamed the Vault, because their mystery-shrouded meetings were held at the Boston Safe Deposit and Trust Company). The city’s business establishment, along with its daily newspapers and the Catholic archdiocese, persuaded city officials to create the Boston Redevelopment Authority (BRA) to carry out the local version of the urban renewal program.

Once in office, Hynes hired Rappaport as one of his top aides. With Rappaport serving as Hynes’s conduit to the business leaders, city officials targeted the West End for redevelopment, proposing to build luxury apartments near the downtown (another part of which was razed to build what is now Government Center). They hoped to stem the exodus of middle-class families to the suburbs and justified their decision in the name of “slum clearance.”

But the West End was not a slum, as sociologist Herbert Gans discovered when he lived in the neighborhood and wrote a book about it, called The Urban Villagers, published in 1962. Gans described the West End  as a lively, working class community of three- to five-story apartment houses – not the blighted slum the city’s establishment claimed. A potpourri of immigrant groups and a small number of African Americans lived together in relative harmony, Gans wrote, their lives centered on their families and the churches, synagogues, schools, settlement houses, and small shops that dotted the West End, at the foot of Beacon Hill.

In April 1958, the BRA  gave West End residents and shopkeepers formal notice that their homes and businesses would be taken by eminent domain. The community itself was not well-organized and had no representation on the city council, then comprised of at-large members. Because this kind of wholesale neighborhood destruction was unprecedented, few West End residents knew how to fight City Hall.

By November, almost half of the 2,700 households were pushed out. By 1960, almost the entire 52-acre neighborhood was gone.

The city government promised the West End’s property owners  that they would be fairly reimbursed for their buildings, and told both homeowners and renters  that they would be relocated to comparable low-rent housing, including the new apartments to be built where their homes had been. All these promises were broken. According to research done in the early 1960s by Chester Hartman, a city planner at Harvard, West Enders were dispersed all over the Boston area. Almost all of them had to pay considerably more rent after they were forced to move. Marc Fried, a psychology professor at Boston College, interviewed the displaced residents. He found that they suffered emotionally from the loss of their community ties, calling his study “grieving for a lost home.”

After Rappaport left City Hall, city officials chose him as the developer of the West End. The city sold him the land for the bargain-basement price of $1.17 per square foot for residential parcels. Additional federal funds and insurance subsidized the development itself. The John Hancock Insurance Company – one of Boston’s most prominent companies —  underwrote the mortgage for Charles River Park.

Political squabbles between Rappaport and next mayor, John Collins, delayed construction of the project, however, and he did not complete Charles River Park until the early 1970s. The project included 2,300 luxury apartments, two swimming pools, a tennis club, a hotel, two office buildings, parking garages, and a shopping center. They stand where the houses and shops of the West End once existed.  Ironically, the luxury high-rise towers are most famous for the sign: “If you lived here, you’d be home now.”

Rappaport used the profits from Charles River Park to expand his real estate empire. In 2006, Boston Magazine estimated Rappaport’s net worth was about $300 million.

Rappaport never expressed any regret for his role in the destruction of the West End, one of the most tragic chapters of Boston history. He became a force in Boston politics. For decades, his fundraising ability and political clout were so effective that the local news media labeled him the “10th city councilor” (when Boston still had only nine council members). In 1974, he persuaded Mayor Kevin White and the City Council to exempt Charles River Park from the city’s rent control law. The next year, he convinced them to start phasing out the tenant protection law by adopting vacancy decontrol, which removes apartments from rent control when a tenant moves out.

In 1990, Rappaport arranged for the Boston chapter of the American Jewish Committee to give him its Community Service and Human Relations award at the Four Seasons Hotel. Nine of the 13 City Council members showed up to honor the man with deep pockets for political candidates. (Globe columnist Alan Lupo noted that the assembled council members had received at least $8,800 in campaign donations from Rappaport.) Tenant activists, several rabbis, and former West End residents who had been displaced by Rappaport’s project three decades earlier protested outside the hotel to rebuke the group for honoring the developer.

Rappaport sold off the Charles River Park development in 2000 and expanded his efforts to cleanse his reputation by donating money to high visibility institutions. In 2000, he endowed the Rappaport Institute for Greater Boston at Harvard in 2000 and the Rappaport Center for Law and Public Policy at Suffolk University. The latter program moved to Boston College School of Law in 2015, thanks to a $7.5 million grant from Rappaport. Ironically, one of the recipients of a Rappaport fellowship at Boston College was Michelle Wu, who won her recent mayoral race in part by proposing a new rent control law, an idea that Rappaport bitterly opposed throughout his life.

Rappaport also spread around his ill-gotten gains to Smith College, Massachusetts General Hospital, McLean Hospital, the deCordova Museum, and Brigham and Women’s Hospital.

Rappaport’s public relations strategy obviously worked. In 1998, for example, Suffolk University – a recipient of Rappaport’s largesse, awarded him an honorary doctor of laws degree. On his 88th birthday in 2015, the Boston City Council declared that August 15 will be known as “Jerry Rappaport Day.” In a tragic irony, they named a new street in the West End “Rappaport Way” in his honor.

Upon his death, the Globe obituary and tributes from officials at Harvard, Boston College and elsewhere portrayed Rappaport as a selfless do-gooder rather than a rapacious developer.

The wholesale destruction of the West End is now considered the worst kind of urban planning: using the wrecking ball to destroy low-income communities and replace them with enclaves for the affluent. The West End redevelopment served as a warning to other Boston neighborhoods that they had to organize to have a voice in the planning process. The urban renewal program remained a battleground into the 1970s, mobilizing grassroots activism in the South End, Charlestown, East Boston, Roxbury, and Dorchester.

Rappaport never completed his West End project. A 1.5-acre parcel near North Station remained undeveloped for more than a quarter of a century.

Soon after Ray Flynn took office as mayor in 1984, he told his aides that he wanted to build affordable housing on that site. Flynn met with a group of former West End residents and then announced a public competition for the long-vacant parcel. The competition was stalled when Rappaport sued the city,  asserting his right to develop the site. Appraisers hired by the BRA valued the property at $15 million, but Rappaport insisted that he should get it for about $100,000, its 1960 value. In 1990 the Massachusetts Appeals Court upheld the city’s rights, clearing the way for the development. A few months later, the city selected the Boston Archdiocese’s Planning Office for Urban Affairs, which had a long track record of building affordable housing, to transform the vacant parcel into a housing development.

In 1995, to Rappaport’s chagrin, an 183-unit mixed-income housing complex called Lowell Square was built on the site, named after one of the old neighborhood streets eliminated by urban renewal.

Meet the Author
Meet the Author
Boston history is filled with people who used their wealth and power to promote the common good. Jerome Rappaport was not one of them.

Peter Dreier is professor of politics and founding chair of the Urban & Environmental Policy Department at Occidental College. From 1984 to 1992 he served as Mayor Ray Flynn’s housing deputy and as the Boston Redevelopment Authority’s director of housing.