In three US cities, three longtime mayors prepare exits. What legacies?

Call them the hipster, the billionaire, and the boss.

Three mayors of three cities, each having served at least three terms, are now preparing to exit the municipal stage after more than a decade shaping major metropolitan hubs – and perhaps the American urban landscape, too.

There's R.T. Rybak in Minneapolis, the mayor known for crowd-surfing at an alt-rock venue made famous by Prince, and leading 30,000 zombies on a city-sanctioned pub crawl – and hosting its contest to see who could eat the most brains (pork brains in tacos, that is).

There's Michael Bloomberg in New York, the media mogul and world's 13th-richest man, the mayor of the nation's financial central server, ticking off the secrets of his success with a simple Wall Street mantra: Arrive early, leave late, eat lunch at your desk.

Then there's Thomas Menino in Boston, the five-term septuagenarian mayor cut from a sepia-toned era of backroom power brokers, a politician who has shaken so many hands, attended so many ribbon-cuttings, and sat with so many parents at Little League games that today almost half of Boston's residents say they have met him personally.

Come Nov. 5, voters will elect successors to the men who have practically become the public faces of their respective cities. It will mark the first time this century that three mayors who've served at least 12 years in major cities will leave office at the same time.

Their impending exits, given the influence the men were able to wield, offer an opportunity for a retrospective look at the state of the American city and powerful chief executives. Though they have different backgrounds and personalities – not to mention different leadership styles – their goals and priorities were remarkably similar.

Each has sought to transform the rusted cranks of urban capitalism, bringing high-tech businesses and services into revitalized city centers and waterfronts, while at the same time trying to remake their cities into safe, healthy, and pleasant places to live again.

They represent, too, an emerging urban politics, combining a business-friendly ethos, a commitment to public safety, and a quest for more-efficient municipal services. (Each understood that neglected potholes could sink a mayor as much as anything else.)

This included more bicycles and fewer guns (Mayor Bloomberg and Mayor Menino cofounded Mayors Against Illegal Guns in 2006, and Mayor Rybak was one of the original 15 members, who now number more than 1,000); new construction, but with tighter environmental regulations; and improved public transportation, moving cars out of view.

"There are two ways, not mutually exclusive, of understanding a city," says Ken Sherrill, professor emeritus of political science at Hunter College in Manhattan. "One is as an economic engine; the other is as home to millions and millions of people. The trick is to get the two of those things to fit together."

This can be a tough fit in the mosaic of cities, however, which some have called "arenas of contested identities." And these mayors' focus on their cities' fiscal engines – and on luring professional classes – has led at least some poor and minority residents, as well as municipal unions and the working classes, to feel left out, or priced out, of the transformations that have taken place during the past two decades.

"In terms of Boston, I guess you could say Mayor Menino was able to bring to fruition the dream ... of making Boston a world-class city," e-mails Tom Whalen, associate professor of social science at Boston University. "It certainly has become that with the development of the Seaport District, [and] the continued growth of the medical, financial, and higher-education sectors of our local economy.

"The problem is, however, that a rising tide does not lift all boats when it comes to Boston," Mr. Whalen continues. "Middle-class families are being squeezed out by high rents and property values, and the gaps in income and quality education opportunities from those on top of the socioeconomic heap and those below them have widened considerably."

Income gaps are widening, in fact, in each of these cities. In 2008, 1 in 5 Boston families with children under age 18 lived below the poverty line. In 2012, 1 in 4 of these families was scraping by.

In Minneapolis, too, families with children under 18 living in poverty jumped from 23.5 percent in 2008 to nearly 27 percent in 2012, even as the share of families making more than $200,000 a year climbed from 7.3 percent in 2008 to 9.6 percent in 2011, according to estimates of the Census Bureau's American Community Survey.

Still, both Rybak and Menino are mostly beloved as they leave office, opinion polls show. The Minneapolis mayor won all three of his elections by no less than 60 percent, including a 74 percent landslide in 2009. And though Menino's victory margins have narrowed from 76 percent in 2001 to 57 percent in 2009, his dominance of Boston politics has remained unquestioned for two decades.

Bloomberg, however, has led a city ambivalent about his leadership – especially among the city's poor and working classes. He won just over 50 percent of the vote in 2001, but a strong 58-plus percent showing in 2005 was followed by a surprisingly narrow 50.7 percent of the vote in 2009 – a third term he arranged by changing the city's previous two-term limit.

He has sounded cranky in the final months of his tenure, bristling under a barrage of criticism during the Democratic primary, won by the populist liberal Bill de Blasio, whose campaign theme, "a tale of two cities," resonated with voters.

Though New York has seen record-setting drops in crime, a robust economy, and glistening new high-rises, Bloomberg's defiant defense of the police department's stop-and-frisk tactics alienated most of the city's minority populations.

Bloomberg has been unapologetic, too, about widening income gaps, promoting Manhattan as a "luxury brand" and saying during his weekly radio show in September that it would be a "godsend" if the city could lure more billionaires like him to the city. True, the income gap would grow even more, he said, but the result would be a boon for all New Yorkers. "[We] take tax revenues from those people to help people throughout the entire rest of the spectrum," he said.

This seeming elitism rubbed many voters the wrong way. "Unhappiness with Bloomberg was about his style of governing, not nearly as much about the substance of what he did," Professor Sherrill says. "What Bloomberg did, for better or for worse, was to pay attention to people who he viewed as the economic future of the city, and to make sure that they were comfortable and happy.... This distinguished them from, say, parents of kids who go to public schools."

In all three cities, the incoming mayors will inherit restless municipal unions. New York's public employees have mostly been working under expired contracts for years and are demanding back raises. Union contracts in Boston loom, and Minneapolis's police and fire departments have struggled with cuts and unpopular commissioners.

But the next mayors will also try to build on their predecessors' accomplishments. From new bike paths to tree-lined walkways, low crime and a climate allowing businesses to flourish, the legacies of these long-term mayors will set a template for those to come.

'The hipster'

In style and substance, R.T. Rybak embodies the transformation of cities from eight-cylinder, smoke-belching engines of manufacturing to the glowing electronic hum of open-floored tech start-ups.

By all accounts, including his own, Rybak faced a steep learning curve when he took office in 2002. A Minneapolis native, he had never before held office, and his background included a hodgepodge of civic-minded positions. After graduating from Boston College in 1978, he worked through the 1980s as a journalist for the Star Tribune in Minneapolis, going on to run the Twin Cities Reader, and launch Q Monthly, a gay and lesbian newspaper. He then became involved in digital journalism, heading Internet Broadcasting Systems, which ran news websites across the United States. He stepped into community activism, memorably participating in a "pajama protest" in which residents spoke about losing sleep because of noise from the area's airport.

After defeating a two-term incumbent, Rybak immediately addressed budget shortfalls, trimming services and raising property taxes. He cruised to reelection in late 2005 and won further praise for his handling of the collapse of the I-35W Mississippi River bridge in 2007. Although 13 died and 145 were injured, many attributed the city's organized, efficient response to Rybak's prescient planning. He was reelected two years later in a landslide.

Rybak has cited the transformation of the Grain Exchange – for 125 years a trading floor and marketplace for Midwestern grains – into a center for the emerging technology community as one of his "favorite things that ever happened" during his 12 years as mayor. After persuading tech companies to forgo the suburbs and move into the heart of Minneapolis, Rybak renamed the building the "brain exchange."

"Talent is very mobile these days," Rybak told Minnesota Business Magazine earlier this year. "Having your city have a hip vibe to it is about more than just having fun. It literally brings dollars into our pockets. The cooler we are, the more we can attract talented people to keep our businesses on the cutting edge and often start new ones that break new barriers."

'The boss'

When Thomas Menino began his political career in 1968, US cities were entering an era of off-the-charts crime, hollowed-out neighborhoods resulting from shipped-out manufacturing jobs, and a flight of mostly white residents to the cul-de-sacs of the suburbs.

Upon graduating from high school, young Tom resisted his father's push to go to college. "He used to say, when I got after him to go to college, he'd say, 'Truman never went to college.' He told me that a thousand times," his father said in a 1983 interview. After eventually landing a low-level job with the Boston Redevelopment Authority, Menino began learning to play the blood sport of Boston politics.

He became a master of the "reward allies, punish enemies" webs of power, was elected to the city council in 1983, and became mayor 10 years later. Previous mayors had focused either on the downtown or on outlying neighborhoods, but Menino focused on both the city's economic engine and the places where people live.

"What Mayor Menino has been able to do quite brilliantly – he is probably the most brilliant politician I've seen – he was able to really bridge both worlds," says Rosemarie Sansone, president of the Downtown Boston Business Improvement District. "He was in the neighborhoods, attending events ... but he also treated the downtown area as a neighborhood itself."

Over Menino's 20 years in office, the job became less one of presiding over urban decay than of harnessing the glittering energy of growth. After balancing budgets and restoring Boston's fiscal health, he led the revitalization of the old industrial seaport – one of his most significant accomplishments. The 1,000-acre waterfront in South Boston is now host to tech start-ups – as well as the eclectic art and music scenes that the firms' youngish, buttoned-down workers prefer. "The Innovation District," as it is known, may seem an unlikely legacy for a technophobe mayor who banned voice mail at City Hall his entire tenure – until relenting just this year.

"Boston's population is growing, and so is our economy," Menino told an audience during a June 2011 address at Boston College. "Employers today want their employees to be close to each other; they want to be close to other innovators, close to transportation – they want to be close to the world."

'The billionaire'

New York's "Silicon Alley" has long been a mecca for tech companies, but Mayor Michael Bloomberg has continued to boost the industry anyway. That has helped to make the tech sector the second-largest contributor to the wage base of an economy renowned as a capital of finance, real estate, and media, according to a study commissioned by the mayor's private foundation.

Bloomberg, Boston-born and Harvard-educated, became a successful trader with the investment firm Salomon Brothers. In the early 1980s he founded a firm that used electronic terminals to provide investors with quick, efficient market information, displayed in easy-to-analyze graphics. The Bloomberg terminal changed how Wall Street operated, and Bloomberg's gauging of his industry's technological future eventually allowed him to reap the billions that now make him one of the richest men on the planet.

"Bloomberg's greatest strength, and greatest accomplishment as mayor, too, was thinking long term," says Professor Sherrill of Hunter College. "He was seriously planning for the future in a way ... unlike any mayor in the city's history – constantly thinking about where the city is going to be 25 or 50 years from now."

The Bloomberg vision emphasizes pleasant, livable streets. He altered traffic patterns to create esplanades and approved a network of green-painted bike paths to go along with the city's buzz of yellow cabs. He has required apartment landlords to replace inefficient oil burners with cleaner-burning heating systems. He has also pretty much banned smoking in public spaces, though his stalled effort to halt sales of sugary drinks and sodas has drawn contempt in some quarters.

Like the other mayors, Bloomberg departs amid simmering resentments from those on the fringes of the new urban landscape. In each city, the incoming mayors – the first their residents have known in at least a decade – face growing income disparity and poverty, restless unions, and aging school systems where students lag far behind the technological revolutions in the revitalized city centers.

Looking ahead, Bloomberg is poised to use his billions to pursue philanthropic and policy projects, at least for the time being. Rybak, a vice chairman with the Democratic National Committee, has a bright political future – though he has resisted joining the Obama administration, eyeing instead the Minnesota governor's mansion, should it become available. And after 40-plus years in politics, Menino will exit the political stage, and perhaps public life, into a grateful city.

"He showed enormous leadership," Ms. Sansone says. "He showed everyone how much he cares [for] and loves the city, and that was breathtaking for everyone."