The City on a Hill: Transcript

May 17, 2023

JAMIE RICHARDSON: The JFK35 podcast is made possible through generous support from the Blanche and Irving Laurie Foundation. 

JOHN F. KENNEDY: Today, the eyes of all people are truly upon us. And our governments in every branch, at every level, national, state, and local, must be as a city upon a hill. 

MATT PORTER: When President Kennedy told the Massachusetts legislature that the United States must be like a city on a hill, he was using the same language used to describe Boston in the Massachusetts Bay Colony since the 1600s. Today, we look back at some of Boston's notable mayors who left their mark on the original city on a hill, including President Kennedy's grandfather John Fitzgerald. All that and more next on this episode of JFK35. 

JOHN F. KENNEDY: And so, my fellow Americans, ask not what your country can do for you, ask what you can do for your country. 

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MATT PORTER: Hello. I'm Matt Porter. Welcome to our final episode for this spring season of JFK35. Today, we are taking a local look at the city of Boston and its past leaders since it first established the mayoral system in the early 19th century. Since colonists first established the area, Boston has been described as a city on a hill or a city to be looked to as an example for others. Today, we'll look at some of Boston's past leaders and how each left their own marks on the city. We'll also look at Boston's newest mayor and how she could be the next leader to leave her own legacy in Boston. 

MICHELLE WU: Boston was founded on a revolutionary promise that things don't have to be as they always were, that we can chart a new path for families now and for generations to come grounded in justice and opportunity. 

MATT PORTER: These are the words from Mayor Michelle Wu as she took the oath of office in November 2021. As one of the first cities in the United States to establish a mayor and city council in 1822, the city of Boston has a long history of leaders who endeavored to remake it for the better of its citizens. The city of Boston has been looked to as an example for the rest of the country during its almost 400-year history. 

John Winthrop, the first governor of Massachusetts, dreamed of Boston and the Massachusetts Bay Colony as a place that would be an example for the rest of the new colonies and the world. He said in the sermon in 1630, we shall be as a city upon a hill. The eyes of the world are upon us. Boston historian and University of Massachusetts Boston professor Vincent Cannato says this philosophy expressed first by Boston's early Puritan leaders has lived on through today. 

VINCENT CANNATO: It's the idea that Boston must be a beacon. It must be sort of a place of light that can show, the rest of the country the rest of the world what good government would be in the idea of Winthrop speech.

MATT PORTER: The idea would be so ingrained in Boston's ethos that President Kennedy would reference it in his farewell speech at the Massachusetts State House before leaving for the White House in Washington. 

JOHN F. KENNEDY: Today, the eyes of all people are truly upon us. And our governments in every branch, at every level, national, state, and local, must be as a city upon a hill, constructed and inhabited by man aware of their great trust and their great responsibilities. Courage, judgment, integrity, dedication-- these are the historic qualities of the Bay Colony and of the Bay State, the qualities which this state have consistently sent to this chamber here in Beacon Hill in Boston and a Capitol Hill back in Washington. 

VINCENT CANNATO: By the 20th century, the city on the hill means during the Cold War that America is going to show itself a beacon of democracy and freedom. 

MATT PORTER: Locally, Boston has had several leaders that each influence the city in ways that still echo today. New Mayor Michelle Wu and her emerging group of supporters could once again alter the face of Boston. Before that, we will look at some of those past leaders that left a lasting legacy on the city on a hill. Our story starts with Boston's second mayor who had set many of the precedents for all others who followed. Mayor Josiah Quincy served from 1823 to 1828 and developed the roadmap on how a mayor could help shape the city. 

VINCENT CANNATO: Today, I think we have the idea that the government does everything. When there's a problem, one goes to the government. Government creates an agency. Government can solve problems. But that's not a concept in the early 20th century. 

MATT PORTER: Known as the great mayor, Quincy used his mayoral powers to reorganize and create professional police and fire departments. And in a controversial move for the time, he also used his powers to acquire land near Faneuil Hall through eminent domain and redevelop it as a commercial space for the public now known as Quincy Market. 

VINCENT CANNATO: So this is the idea of government, in this case, city government, a mayor, using those powers to improve life in the city.

MATT PORTER: Cannato says Quincy's era was a period where local leaders were beginning to take a more active role in developing cities, which had previously been left up to private interests. Another example of this type of change was when New York City set aside 778 acres of Manhattan land for the public and what is now known as Central Park. 

VINCENT CANNATO: That idea is slowly gaining hold that the way a city develop is not just going to be through private interests, not just through private landowners and business interests, but that the government is going to have a role in creating spaces for the public and trying to create if not a more equitable city at least one that's looking out for the public good not just for the private interests. 

MATT PORTER: Another mayor to change the city and its priorities came to prominence at the turn of the century and also had ties to President Kennedy, his grandfather John Francis Fitzgerald. He took office for the first time in 1905. Fitzgerald was a different character compared to other previous more straight-laced mayors. 

Historian Robert Dallek referred to him as a quote, "pixie-like character who was a showman who could have been in vaudeville." He had a penchant for singing in public, particularly the popular barbershop ballad "Sweet Adeline." His cheerful demeanor led his supporters to give him the name Honey Fitz. And his administration would be that of another major change for the city of Boston, which until then had been dominated by wealthy and influential Protestant leaders often referred to as Boston's Brahmins. 

VINCENT CANNATO: And the Brahmins are, generally speaking, the Protestant, mostly of British descent, the kind of more wealthier elites of Boston, those living up on Beacon Hill, the ones who control the banks, the ones who control the cultural institutions in the city, the ones who are descended from the Puritans. These are the Brahmins who are Protestants. So you have a religious conflict between Protestants and Catholics. You have an ethnic conflict between people of British descent versus people of Irish descent. And you have a class conflict, wealthier people versus people who are further down the socioeconomic ladder. 

MATT PORTER: Fitzgerald was responsible for organizing new Irish immigrants and their descendants into a political force. Through his leadership and policies, the Irish would begin to have a voice in Boston government that would dominate politics for the next century. 

VINCENT CANNATO: As a big proponent of immigration at the time, he was a critic of immigration restrictions. So I would say this idea that not just the elite but power should be broadly shared among newcomers and other groups. And that was an important thing. 

MATT PORTER: Fitzgerald would spend millions of dollars investing in Boston ports, which would cement the city as one of the most important seaports in the first half of the 20th century. The new ports increased industrial jobs that many of his Irish constituents could take and build more prosperous lives. Fitzgerald also recognized the needs of working class Irish families in Boston. He established city funded initiatives, including free ferry rides, new public spaces and parks, including the Franklin Park Zoo, and new educational and medical facilities. 

During his tenure, Boston would also be the first city in the United States to open a subway, expanding affordable public transit for city workers. Fitzgerald was committed to investing in the working areas of Boston after years of watching previous administrations investments in the financial and business sectors of the city. 

VINCENT CANNATO: The idea that a development is not just going to be for downtown and for the elites but it's also going to be more broadly shared. 

MATT PORTER: The next Boston Mayor who would succeed Fitzgerald by beating him at his own strategy would be James Michael Curley. Like Honey Fitz, Curley won leaning on the Irish vote in Boston. But unlike Fitzgerald, Curley took an even more adversarial tone to downtown interests and the Boston Brahmins. 

VINCENT CANNATO: Curley represented the neighborhoods. And he had no interest in downtown. He had no interest in appeasing the bankers and the other interests. And he was going to use policies and government monies to improve the neighborhoods, to improve his people, so to speak. 

MATT PORTER: Curley spent most of his power continuing to direct monies to beaches and public bathhouses in Irish neighborhoods, along with schools and public libraries. He was seen as a hero to the voters in those neighborhoods. But his aggressive policies, including increasing taxes on Boston's financial sector, drove some businessmen and corporations out of the city. 

VINCENT CANNATO: Where Curley was really in some ways a cultive personality, his personality. And he drew that line between the Brahmins and Irish incredibly sharp. He could play to his audience, and he could really tick off the Brahmins and knew how to kind of stick it to them. And his constituents, Boston Irish, loved it. They loved it when he stuck it to the Brahmins. 

MATT PORTER: Curley served multiple non-consecutive terms in office. By the end of his time in the mayor's office, Curley's hostility towards business interests and Boston's economic prowess compared to other American cities was greatly diminished. 

VINCENT CANNATO: By the early '50s, the tallest building in Boston is the Custom House Tower. There are no skyscrapers. The great thing that defines a modern city, Boston doesn't have it. 

And people-- they were losing tax money. They were losing their tax base. They had very high taxes downtown. But businesses were leaving. So that was hurting the city, in general. 

MATT PORTER: In addition, Curley played it fast and loose when it came to abiding by the law regarding his finances and fundraising. By the end of his last term, he faced federal felony charges related to bribery and eventually was convicted of mail fraud. Curley is the only Boston Mayor to have served part of his term in jail. 

VINCENT CANNATO: He always stayed one step ahead of the law. And he was able to kind of just live on the edge of ethics and legality. And he got sent to prison down in Danbury while he was mayor. He was still mayor. And he's serving time in prison. And by this time, he was older. 

He was much less effective in his final term. The game he was playing or had played 20 years earlier, it did not have as much of an audience. There were still people who liked it. But there's a rising generation of Boston Irish who are more middle class, who more moving up the socioeconomic ladder and less interested in Curleyism. 

MATT PORTER: The next mayor to leave a major mark would be Curley successor in John Hynes. Hynes was a career public servant working for the city for 40 years. The audacity of Curley's final years in office would convince him to run against his former boss. 

VINCENT CANNATO: And what ends up happening is Curley is in jail. And a man named John Hynes, who's the city clerk, is the next in line. He runs the city. And he's kind of just a bureaucrat. Curley comes back. 

One of the first things he says is that he Curley had done more-- it was something like Curley had done more in one day than had been done in the months that he was in jail. And that was a slap at Hynes. And Hynes, who was just a mild mannered bureaucrat, decided, you know what, I'll run for mayor. 

MATT PORTER: Hynes brings a renewed focus on the downtown in ways that hadn't been seen in most of the first half of the 20th century. He founds the Boston Redevelopment Authority, which would introduce projects around the city to bring wealth and investment back into the city's downtown. His most recognizable positive impact on Boston may be the Prudential Center Tower and his work on revitalizing the struggling Back Bay neighborhood. 

VINCENT CANNATO: What you begin to see is the Boston economy begins to grow again and begins to be slowly rebuilt. I mean, think about John Hancock, Prudential, businesses coming into Boston building skyscrapers. You get more jobs. 

And these higher end jobs, these are more for college educated, upper-middle-class people coming into the city. Boston focuses as today sort of the eds and meds. Schools and hospitals seems to become a focus, a driver for the Boston economy. 

MATT PORTER: But his efforts with the BRA to revitalize Boston came at a cost. His administration would knock down the entire West End neighborhood of Boston to build the Central Artery Highway through the city, possibly one of Hynes' biggest mistakes. The federal government together with the city and state would put the highway underground decades later in one of the most expensive public works projects ever seen at the time. 

VINCENT CANNATO: We don't do that anymore, the Big Dig, put that underground. We understand that running highways through cities is generally a bad idea. And, in fact, in the late '60s, early 1970s, Boston is able to stop even more elevated highways. 

MATT PORTER: For mayors like John Hynes and John Collins, who follow years of Curley style progressive politics, their administrations represent a shift back towards a focus on business and economic interests. 

VINCENT CANNATO: For many, that represented urban renewal, which was we need-- the city believed, Hynes then Collins believed that the city was losing tax revenues. So you had to take downtown real estate and make that as profitable as possible and attract the middle class to come in to Boston and then bring jobs into Boston and rebuild the economy to help the city prosper. But as I said, the downside was it was a policy that was not very sensitive to the neighborhoods, to the working class, to those who are not elites. 

MATT PORTER: Then in 1993 came a mayor who attempted to bridge the divide between neighborhood and downtown interests. 

THOMAS MENINO: Whether you are somebody who has felt left out of politics and government and attempt to give up on our city, whether you are a young person thinking about dropping out of school or whether you are a business owner or a worker who has been laid off, whoever you are, this is the promise I make to you today. I dedicate my time as mayor of Boston to making this city work as well for you as it worked for me and my family. 

MATT PORTER: Mayor Thomas Menino would serve from 1993 to 2014 as the city's longest serving mayor. 

VINCENT CANNATO: So Menino comes in. He's kind of a lifer in politics. He's not kind of underrated. He doesn't have a big profile. And he comes in. 

He calls himself an urban mechanic. I'm a pragmatist. I'm here to fix the city, to deal with problems, fix problems. I'm a neighborhood guy. But he's a neighborhood guy who had good relations with downtown, with business. He didn't see the two as diametrically opposed. 

MATT PORTER: Menino would attempt to fix the mistakes of the past. One of the most visual examples of that effort is the park that replaced the elevated Central Artery Highway, the Rose Kennedy Greenway. Menino was a key figure along with Senator Ted Kennedy in working to right the wrongs of the past and put the interstate highway underground. 

Burying the highway that cut the city off from its seaport, he replaced it with 1 and 1/2 miles of park and public space named after President Kennedy's mother Rose Kennedy. The Park is managed by a nonprofit organization which maintains the grounds and supports events and programs in the park that are available to all. 

VINCENT CANNATO: But now the North End was able to be reintegrated in. And you get the Rose Kennedy Greenway, which is one of those kind of public projects of the last 20 years, a public works project, that really has a huge impact. It's a beautiful park, people there all the time. There's always things going on. And it instead of this gash coming right down the middle of Boston, you have beautiful green space that's also well used by the public. It's a great urban space. 

MATT PORTER: Menino's long tenure in Boston is a reflection of his ability to balance downtown interests along with the working class neighborhoods around the city center. However, even Menino's administration struggled to be equitable in some of his policies. In the last 20 years, Boston's wealthier downtown neighborhoods have seen spectacular growth. However, that growth has come at a cost with some of the poorest Boston residents paying the price. 

VINCENT CANNATO: The downside of the renaissance of Boston, the renaissance of American cities during the '90s and early 2000s was that it leads to gentrification. So it leads to higher real estate value, higher costs, which drive out much of the middle class and make cities very expensive and creates inequality. So you have cities that are very wealthy and also very poor. 

MATT PORTER: And that brings us to Boston's next chapter, a chapter that will be written by the city's first elected woman of color, Mayor Michelle Wu. Like JFK's grandfather Honey Fitz in the 20th century, Wu leads a new diverse coalition of underrepresented voters. Her 21st century coalition includes deep support in some of the poorest and most struggling neighborhoods of Boston. 

For example, one of her primary goals has been to restructure the Boston Redevelopment Authority, which has been responsible for destroying some of Boston's working class neighborhoods in favor of the interests of wealthier citizens and special interest groups. Wu came into Boston promising to change how the city looks at development, to make its investments more equitable for all residents. 

MICHELLE WU: When we make City Hall more accessible, we are all raised up. When we communicate in many languages, we all understand more. And most of all, when we connect the power of city government to the force of our neighborhoods and communities, we see how much is possible for our city. 

MATT PORTER: Joining us now to discuss the state of the city of Boston and how Michelle Wu may be the next mayor to make fundamental changes for the city is Boston Globe columnist Shirley Leung. Shirley, thanks for joining me today. 

SHIRLEY LEUNG: Thanks for having me, Matt. 

MATT PORTER: So, Shirley, I want to get into where we left off with the historian, which was Mayor Thomas Menino and Mayor Walsh. They sort of found a Boston, which maybe had a bit of a split personality with two different sides. Why don't you go in a little bit of detail of where has the city come since Mayor Walsh and Menino left their mark on the city? 

SHIRLEY LEUNG: When I think of Menino and Walsh, I think of almost a 1, 2 punch in terms of shaping modern Boston. I mean, really new neighborhoods were formed. Look at the Seaport district. When I started covering the Seaport, two decades ago, it was parking lots, dusty parking lots. And now it's glitzy towers. It's multimillion dollar condos, fancy restaurants. You have marquee companies who want a presence there from Amazon to Vertex. 

And that's just happened over the last 20 years. You think of Fenway. There was not much going on in Fenway around Fenway Park. But in the last 20 years, again, a new neighborhood has risen, residential, fun restaurants, hotels. It's another new neighborhood of Boston. So I see them as kind of a 1, 2 punch in building a modern Boston. 

MATT PORTER: And, of course, that sounds on the surface excellent for the city, and it definitely has benefited the city. But, of course, you also then have critics of that development saying that it wasn't quite equal, and it sort of left some residents behind, particularly maybe the people who have to get around and work in those new restaurants and places in the Seaport and Fenway Park. Do you want to talk about what those critics have said about that development? 

SHIRLEY LEUNG: I mean, the critics, including the Boston Globe, right? We did a 2017 Spotlight Series on race, and one day was dedicated to the Seaport. And how can this be the newest neighborhood of Boston but also the whitest? And we documented how there are very few Black tenants there. There very few Black homeowners, and that's absolutely true. 

One of the things that has happened with the creation of new Boston-- it's left a lot of communities behind. Whether it's Black developers or construction companies, Black restaurant owners, they haven't been part of the new and very wealthy part of Boston. And that's the next phase. That's the challenge of the current Mayor Michelle Wu to create a more equitable Boston. 

And you're starting to see some of that happen, especially in the Seaport now with what is known as the Massport model. And that is something that the Massport Authority-- they run Logan Airport. But they're also a major landowner on the South Boston Waterfront. 

And what they've done is said we have parcels. We have some say in the diversity of the construction companies and the developers, and we're going to sign a score. When we put out our parcels to bid, diversity will count for 25% of your score in your ability to win this parcel. And a lot of these parcels are very coveted. They're prime real estate. 

And so Massport created this model a few years ago. And now the city of Boston has adopted and others are looking at it as well in terms of driving more diversity, creating more wealth among investors of color, basically owners of construction companies, diverse owners of construction companies and also real estate companies. 

MATT PORTER: Again, we just spoke to a historian before the segment who talked about how President Kennedy's grandfather Honey Fitz was part of this new generation of Irish Americans that basically took over the city from the financial class known as the Brahmins. What do you think about Michelle Wu? She's 38 years old. She is the first woman, person of color elected mayor of Boston. Are we looking at sort of another transitional change type mayor as maybe we saw hundreds years ago with Honey Fitz and the other Irish Americans who took the reins in early Boston? 

SHIRLEY LEUNG: Absolutely. Mayor Wu ran on this campaign, a new Boston. And from the get go, she has almost declared old Boston dead. You can see it in the way she does business, the way she works. The established class of business leaders or politicians and civic leaders, they no longer have the upper hand in Boston. It's a new class of activists, grassroots activists, community organizers, leaders from Mattapan, and Dorchester, and Roxbury, East Boston. 

These are people who usually don't have a seat at the table, and now they do. So you really do feel that change. And it can be a little unsettling right for those who have been part of the establishment for so long and no longer are. That's kind of the tension that's happening in the city right now. But, ultimately, if she can create a more equitable Boston with different voices and people around that table, it will be a better Boston for all in the end. But there are some growing pains right now. 

MATT PORTER: About those growing pains, while she may be this new for us in Boston, as you said, there are still a lot of people from the old guard in control of a lot of the city's mechanics. 

SHIRLEY LEUNG: Right now, it's an unsettling time for her to come in with a new agenda. At the same time, there's a pandemic. There's a lot of economic uncertainty. And she has a lot of big ideas that cost a lot of money, whether it's to create more affordable housing, to control rents, to fulfilling her vision of a new Green Deal. And so she will need partners. 

And a lot of that will come from the business community. And right now, they don't have the best relationship. But it's early days in her administration. It's only year 1. She's entering into year 2. And, plus, she can't change the city culture, the way we've done business overnight. It's going to take some time. 

MATT PORTER: You mentioned the pandemic. And I wonder, do you think the rise of remote work-- suddenly, the major office buildings maybe are sitting half empty. Do you think that actually gives her an opportunity to reshape what those buildings can be and could contribute to? Whereas if there wasn't a pandemic and things were kind of business as usual, there might not be that opportunity. 

SHIRLEY LEUNG: It does give her an opportunity to leave her mark on Downtown Boston. And she has talked about remaking downtown, bringing more diverse businesses. I remember one time during the campaign she talked about empty storefronts in Downtown Boston. Could they be opened up for more child care facilities to make the city even more family friendly and offer more working families affordable places for child care? 

But one of her greatest challenges of her being a mayor and any really big city mayor is the recovery of downtown. Boston is a city where we have a lot of white collar workers who don't have to come into the city, don't have to come downtown to work. They can work from home. And I think right now a lot of companies are trying to figure that out. A lot of companies are in this hybrid work model. 

But the reality is even if you ask your employees to come back three days a week, chances are they're probably only coming back once a week. And that has an impact on the coffee shops, the restaurants, the shops that depend on office workers streaming in every single day. And so the big challenge is what is the value proposition of being in a city like Boston? And it's very expensive to do business here. And it's very expensive to live here. 

So even for workers, they have to decide do I want to be in Boston? Maybe I should go to the South. Maybe I should go to the Midwest where it's much cheaper to live. And then I can work remotely for a company based in Boston. 

MATT PORTER: Right. You mentioned that it's hard for so many people to live here. And I believe that same Boston Globe Spotlight Report talked about the net worth of Black Bostonians being $8. 

Again, we've talked about Boston wanting to serve as the city on the hill. But really for the last century, it has not been when a comes to incorporating its Black citizens, its other people of color into the fabric of its community. How does Boston become that city on a hill again? 

SHIRLEY LEUNG: I have to say in the last 20 years that dynamic is rapidly changing. I guess I shouldn't say even in the last 20 years. I want to say the last five years. You're starting to see a change in the power base. I mean, think about the election of Ayanna Pressley as a Black congresswoman from Massachusetts. Think about the number of women we've elected to Congress. 

Our sitting senior senator is Elizabeth Warren. So there are a lot of women in power now. And then you just look at the diversity across the state in terms of power, Andrea Campbell, first Black woman attorney general of Massachusetts. You think about, of course, Michelle, Wu, first woman elected mayor of Boston, person of color, Asian American. 

And then her cabinet is so diverse. Maura Healey, first woman elected governor of Massachusetts-- her cabinet is shaping up to be incredibly diverse as well, and representation matters. And you're starting to see a huge shift just in the last few years and particularly the last year or two in terms of making sure that we are creating a city and a state that is for everyone. And so I think we have a chance as a city and a state to be a leader on creating a more equitable society. 

MATT PORTER: What are examples from Michelle Wu's State of the City that you think could be a game changer as far as being able to allow these communities to grow where they haven't had that opportunity in the past? 

SHIRLEY LEUNG: One of her big focuses is re-examining development or what she called blowing up the BPDA. And the BPDA is our Boston Planning and Development Agency. And she is looking at streamlining development. She's looking at separating planning from development, so development doesn't drive planning. Instead, it's planning shaping our communities. 

One of her criticisms of the prior administration is that there was a focus on building buildings instead of a focus on building communities. And so you're going to see her do that. And one of the ideas that she had that came out of the State of the City Address is using some of the powers of the city and the real estate power of the state, which is she wants to give developers free land to build housing. And a lot of those parcels will be in the neighborhoods, Mattapan or Roxbury. And so that will create new development and housing in those neighborhoods, affordable housing at that. 

MATT PORTER: And while creating this housing to ensure that people can live here, the other question is to make sure that Boston is habitable going forward. Boston is a coastal city, which means it's going to face some really serious climate change effects in the next 20, 30, 40, 50 years. Even here at the Library, we're making serious plans. We are right on the water. So how do you think Michelle Wu's plans can also make sure that Boston lives up as a sustainable city and maybe as an example to other coastal cities? 

SHIRLEY LEUNG: I mean, she has a chance to lead the nation on this as a sitting mayor. We are probably one of the cities in the country most vulnerable to rising sea levels. And she first as a city councilor and now as a mayor has made this a priority to protect Boston from rising sea levels. 

And so, again, in her State of the City Address, she talked about this. She talked about how the city is going to lead by example. It's going to require the renovation of municipal buildings or the construction of schools. They're going to be fossil free. And so she is going to do all she can to have Boston lead on this issue, which makes her the right mayor at the right time. And it's going to be expensive. 

And it's going to take a lot of political will. But I think she's very focused on this because she knows what's at stake. More so than many other cities, Boston is vulnerable to flooding. We were built on filled land, tidelands. And so it's going to become very apparent very soon that we've got to do something. 

MATT PORTER: Speaking of lots of money and we got to do something, again, for people who aren't familiar with Boston, the city was the first city in the United States to have a public transit subway system. Again, it was a city on the hill back then. But, today, very few cities would look to Boston to emulate their public transit and subway. What do you think Michelle Wu is going to face as far as trying to also give Boston a 21st century facelift when it comes to its public transit? 

SHIRLEY LEUNG: Mayor Wu-- again, she championed this issue, a free T, what we call a free T as a councilor and then as a mayor. She's made some bus lines free using city money as well as federal relief money. But really the problems of the T are really the governors because the governor controls the state transit system, the MBTA. 

But Mayor Wu already has been outspoken and championed the need for a world class T. I mean, she herself rides the orange line to work. She tries to ride it at least once a week. And she's a regular on the T. And so I think her being outspoken about the problems of the T will go a long way to helping fixing the T because we haven't seen that with Mayor Walsh or Mayor Menino. She's really the first mayor in the modern era to say the T matters to the economic future of Boston. And we deserve a better T. 

MATT PORTER: All of these issues that she's going to have to face, it seems pretty daunting. To wrap up here, again, I'm going to come back to our historian who talked about Boston. And just any city almost works on a pendulum, where sometimes the pendulum swings too far one way and too far the other. If we look at the last 100 years, we discussed John Fitzgerald and James Michael Curley building these amazing public parks or public facilities for the public good. 

And then as the city went on, it kind of went the other way back to developers and finance. And then as we spoke about the beginning of this interview, again, Mayor Walsh and Thomas Menino made amazing contributions to the city bringing the city back to what some would say is a world class city but doing so while maybe leaving certain communities behind. Where do you place sort of all these challenges facing Michelle Wu? And if she's even able to complete a few of these big goals, where do you think this will place her as far as notable mayors from Boston's past? 

SHIRLEY LEUNG: If there can be more affordable housing built, if she can begin the process of protecting the city from rising sea levels, that will go a long way. I think the big question for Michelle Wu is how many terms will it take? Menino was there-- was a four terms or five terms? He was there for probably five terms if it's 20 years. And Walsh was there for almost two terms. And he was able to accomplish a lot, but the economy was strong. Interest rates were low. 

And Michelle Wu doesn't have that kind of tailwind right now. She's facing actually headwinds economically. So I hope she stays for a while to accomplish her big ideas, and her big agenda, and her big ambitions so she can create more affordable housing, re-imagine downtown, and protect the city from rising sea levels. Those would be huge accomplishments. And it's a matter of how quickly can she accomplish those things. 

MATT PORTER: And while many, many people come from Massachusetts and are familiar with the city and familiar with Mayor Wu and Mayor Menino and Walsh, we do have a lot of listeners who aren't as familiar and maybe only hear the stories of Boston like it's particularly bad history on race. They look at Boston as maybe a very insular community that's homogeneous, although I think you and I would know from living here that it's not nearly as homogeneous as maybe outsiders think. 

But, again, as Boston hopes to be that city on a hill, for you, what would you like in the next 10 years people to hear about Boston? What would you want the reputation of Boston to be like for people outside this community who are seeing it from afar? 

SHIRLEY LEUNG: I want Boston to have a reputation as truly being welcoming for all. And it's a place where you can start a company and start a family and feel welcomed, not have any fears of living here. And you can be yourself. I'm a transplant. 

So I grew up in a far suburb of Maryland. And I've been in Boston now two decades. Both of my sons are born here in Boston. And, actually, one of my very first memories of Boston is reading about the Kennedy family. And I grew up with the Kennedy family and kind of fascinated with John Kennedy, with Jackie O, the whole thing. 

And so when I think of Boston, I actually think of the Kennedys. And when I came here and started working here, I fell in love with the city. It felt like home even though it wasn't my home. It's my adopted hometown. And what I love about Boston is I love the civic engagement. And especially the last decade, I love seeing all the women in power, an Asian American as mayor. I've never thought of that. Deval Patrick as the first Black governor. 

I mean, I've seen and live through the changes at Boston. And even at the Boston Globe, we have a first woman as the editor of the Boston Globe now. So you feel the change happening. 

I'm hoping that a decade from now or two decades from now we are seen as the place where anyone can make it. You don't have to be White. You don't have to be Irish. You don't have to have the right connections. Anyone can come here and feel part of Boston. 

MATT PORTER: What a great sentiment to end on, Shirley. And so glad that you came to Boston and felt welcomed and that you've stayed for the last 20 years. Thank you so much for joining us today. 

SHIRLEY LEUNG: Thanks for having me. 

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MATT PORTER: Thank you for listening to today's special episode about Boston leaders. If you're interested in learning about President Kennedy's grandfather John Fitzgerald or other Boston mayors, you can find links to more information at our website JFKLibrary.org/jfk35. If you have questions or story ideas, email us jfk35pod@jfklfoundation.org or tweet at us @JFKLibrary using the hashtag #JFK35. 

If you like what you heard today, please consider subscribing to our podcast or leaving us a review wherever you get your podcasts. Thank you for listening. We'll be back in the fall with a brand new season. Until then, have a great summer. 

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