A Tale of Two Mayors


Elections were held in New York City and Boston yesterday, and both cities re-elected their mayors to new terms.

Yet the true results of these elections were as different as the cities themselves.

In Boston, Mayor Tom Menino won a record-setting fifth consecutive term in office, defeating challenger City Councilor Michael Flaherty by 57% to 42%.

In NYC, Mayor Michael Bloomberg won a third term, but by a narrow margin, defeating insurgent William C. Thompson by 51% to 47%.

Boston’s Menino is being called “Mayor for life” this morning, while observers are reacting with shock that New York’s Bloomberg barely got himself back into office, despite high approval ratings and a staggering advantage in campaign cash.

Both men have come a long way from their childhoods in Boston — Bloomberg left town to become one of the richest men in New York City and the successor to Rudy Giuliani, while Menino has never strayed from his enclave of Hyde Park, and slowly, gradually amassed a iron grip over the city of his birth.

Menino cruised where B-berg struggled yesterday because he knew something that the Wall Street billionaire didn’t — In politics, dogged incumbancy is an unstoppable strategy for maintaining a hold on power.

Tom Menino is an unlikely master politician.

He won the Mayor’s job as an almost anonymous City Councilor in the aftermath of Ray Flynn’s nomination as Ambassador to the Vatican.

Menino isn’t particularly polished. He isn’t a policy wonk. He isn’t a charismatic figure or an imposing tough guy.

He’s also a fairly horrible public speaker, a trait that has earned him the nickname “Mumbles”:

Through four terms in office, Menino has had his share of shortfalls.

A complete lack of transparency — obstruction of transparency, even — created a scandal that engulfed Menino’s top lieutenant, Michael Kineavy. In violation of the law, Kineavy routinely deleted emails that may have implicated the Mayor’s office in political corruption probes surrounding the City Council.

The city’s education system is troubled, an issue that has dogged Menino throughout the past few elections.

The mismanagement of the Boston Redevelopment Authority has led to large-scale debacles such as the giant hole in the ground at Downtown Crossing:

Challenger Michael Flaherty harped on all these topics and more, and even engaged the active support of the #3 contender, City Councilor Sam Yoon, to form a combination platter that local pundits dubbed “Floon.”

In the end, though, it mattered little, as Menino rallied his winning coalition and cruised to victory for the fifth straight time.

As a compelling Boston Globe piece demonstrates, Mayor Menino achieved this success by dogged determination, unflagging hard work, and a unique knowledge of — and connection to — the city voters who have returned him to office time and again:

On their own, they are petty encounters: A couple of “friends’’ of Michael F. Flaherty were admonished by city workers to get off his Facebook page; a state aide got advice from a city official that led to a parking ticket being dismissed; a Sam Yoon campaign office was cited by city inspectors for having too many window signs.

But taken together, these seemingly inconsequential incidents offer a rare window into the workings of Thomas M. Menino’s City Hall, a place where not even the most trivial slights go unnoticed and the smallest opportunities unnourished.

If Menino is the urban mechanic who famously knows every neighborhood in his city, and is regularly seen in them all, it is his sprawling machine that knows every building on every block, and has a reach into nearly every one.

Menino has assembled the most extensive political operation in modern Boston history over his 16 years in office, rivaling that of legendary mayor James Michael Curley. He’s done it the old-fashioned way, by blurring the lines between politics and policy, between city work and campaign work, delivering services to everyday residents and warnings to his rare foes – many of them intended to strengthen his electoral standing.

“You have to give Tom Menino credit,’’ said City Councilor Charles C. Yancey, a 25-year council veteran who has not endorsed in the mayor’s race. “He really has mastered the nuts and bolts of politics in Boston.’’

The focal point of Menino’s operation is dozens, even hundreds, of city workers who make the mayor’s political cause their own. By day, they perform constituent services, enforce city codes, issue parking tickets, and tow cars. By night, they volunteer their time for the mayor, attending community meetings or campaigning on his behalf.

Take the case of Jack Kelly, the city’s neighborhood liaison in Charlestown, who sent a friend an e-mail, according to documents obtained by the Globe, asking that he remove himself from Flaherty’s Facebook group.

“If he gets elected I lose my job,’’ Kelly said in the first message. When the friend didn’t immediately remove himself, Kelly followed up with another saying, “You’re killing me.’’

Or take the case of Michael J. Kineavy, the former iron worker who now holds the title of Boston’s chief of policy and planning, but is better known as Menino’s most trusted political adviser and most effective enforcer.

Kineavy was able to rattle off, in an interview, the number of people – 14 – who attended a fund-raiser for Flaherty’s mayoral campaign. How did he know?

“There was a guy in the room that was ours,’’ Kineavy said. “What’s wrong with that? It’s recon. That’s not even negative. It’s knowing what your enemy’s doing.’

A Boston Globe Poll showed that 57 percent of Bostonians have personally met Mayor Menino, a statistic that no doubt contributes heavily to his success in bringing voters back to the polls again and again.

In an interview this morning on WBUR, local political pundit Larry DiCara noted that the key to Menino’s success is a tried-and-true coalition of voters that have carried him to victory in each election: city workers, African-Americans, Italians and liberals.

Like other candidates before him, Michael Flaherty tried and failed to unseat Menino and strip away a bloc or two from his winning coalition.

Tom Menino doesn’t seem, at first glance, to be a particularly impressive politician.

Yet he has succeeded in obtaining an unprecedented fifth term in office as Mayor of Boston because he has built an unstoppable political machine that exists for one reason alone: to run and control the city of Boston.

Many politicians run for each office with another, higher office in mind. Major figures on both the right and left have won major elective office, only to leverage that position to obtain a better one. We need only look to 2008, when Senator Obama left Washington to run for President after only a year or so, while Governor Mitt Romney stumped down South, dissing his Massachusetts constituents for political props.

Mayor Menino never fell victim to the narcissism that leads so many politicians into the throes of the Peter Principle, obtaining that promotion that’s just elite enough to get them in over their heads. He’s a man of Boston, always has been, and it’s now clear that nobody will be able to force him to relinquish his hold over the city until he himself decides it’s time to go.

Brian Mooney provides a fitting recap:

When he was sworn in as acting mayor more than 16 years ago, no one, not even Menino, could have imagined that he would one day become the virtual mayor for life.

How did he do it?

For more than 16 years, Menino’s City Hall has paid attention to the details – zoning, liquor licensing, and congestion – that affect the quality of life where residents do much of their shopping and socializing.

If Menino has a particular genius, it is that he understands Bostonians want to feel good about their neighborhood. That means visible police, antique street lights, and spruced-up business districts. From Brighton Square to Fields Corner, from Roslindale Village to Grove Hall in Roxbury, commercial districts have better stores and more restaurants and improved sidewalks and traffic controls.

He showed up, which matters a lot in politics. From the day he took office, Menino spent most days on the move, in every neighborhood of the city, meeting his constituents and hearing their hopes and complaints. Like Schaefer in Baltimore, he often took action which produced results that were tangible.

His administration devoted disproportionately large shares of discretionary funds to projects in Roxbury, the long-neglected heart of the city’s African-American community.

On matters of race, gay rights, and other social issues, Menino has been consistently progressive. Hizzoner’s Daley-like political machine tightened his grip on power, but even at its most efficient, a great field organization is worth only a few percentage points in the final vote tally. Menino, however, has sturdy political infrastructure in virtually all 254 precincts. His army on the ground is of every hue and generation, and many are City Hall’s eyes in their neighborhoods.

On Menino’s watch, the city has not suffered the financial crises and social upheavals of previous administrations. Crime and public education, always major issues in big cities, have been managed under Menino.

No one has found the silver bullet to solve the problems of urban school systems, and Menino is no exception. But with much work yet to be done on the schools, many voters seem to have given him a pass on an issue on which he once urged voters to judge him harshly.

Like Tom Menino, Mike Bloomberg was expected to win a new term in office, and he managed to do so. However, it was a victory that required changes in city law, not to mention a vast infusion of the Mayor’s personal wealth.

Bloomberg, a multi-billionaire Wall Street executive, whose visionary company Bloomberg LLP changed the way that bankers consume news, first won office in a tightly contested election against Democrat Mark Green.

After a highly successful first term, he captured reelection by 20% over Democrat Fernando Ferrer — a record for a Republican incumbent in New York City.

From the outset, Bloomberg’s management style was modeled on the one that served him well in the private sector:

Mayor-elect Michael R. Bloomberg said yesterday that he would create a large, open office in the heart of City Hall — modeled after the one that he used to manage his private company, Bloomberg L.P. — from where and he and his top deputies would run the city. Mr. Bloomberg said he would relegate the mayor’s formal corner office to mainly ceremonial purposes.

The decision by Mr. Bloomberg, which he disclosed at a news conference yesterday called to announce the appointment of the United Nations Development Corporation president, suggests a major shift in the way City Hall is going to be run after Mr. Bloomberg takes over next Tuesday from his fellow Republican, Rudolph W. Giuliani. And it marks the clearest example to date of the extent to which Mr. Bloomberg intends to apply practices that he employed in the private sector to his first job in government.

”I will be working surrounded by the deputy mayors and main advisers,” Mr. Bloomberg said. He added: ”I mean, keep in mind there are physical constraints on what you can do at City Hall. But to the extent that that is possible — all my life I’ve worked in the middle, and I plan to do exactly that.”

The Park Avenue headquarters of Mr. Bloomberg’s company is a large sprawling floor of desks and computer monitors, without walls or dividers. His desk is set in a corner, visible and easily accessible to employees. Mr. Bloomberg said that the design of that office was intended to encourage employees, regardless of rank or stature, to approach him with ideas and questions. The open configuration has become a symbol of Mr. Bloomberg’s management style in the corporate world.

Bloomberg’s pragmatic approach and private-sector angle on government seemed to be serving him extremely well as recently as a year ago.

This led Bloomberg into an extended flirtation with the idea of seeking the Presidency as an independent candidate, potentially considering spending $1 billion of his wealth on the effort:

One day last July, Al From received an unexpected call from Michael Steinhardt. From is the founder and CEO of the Democratic Leadership Council, the centrist outfit in Washington that helped propel Bill Clinton into the White House; Steinhardt is the once-hellacious hedge-fund manager turned philanthropist whose name now graces the School of Education at NYU, a former chairman of the DLC, and a friend for decades of Mayor Michael Bloomberg. When From picked up the phone, Steinhardt greeted him thus: “How’d you like to come to New York and have dinner with the next president of the United States?”

From replied, teasingly, “I didn’t realize you’re so friendly with Hillary Clinton.”

The genesis of Steinhardt’s call was a conversation with New York City schools chancellor Joel Klein. Klein said that “Bloomberg was preoccupied—no, that’s too strong a word—that he was really focused on whether he should run for president,” Steinhardt recalls. Steinhardt reminded Klein of his association with the DLC and told him that if Bloomberg wanted to meet From “to get some perspective about the realities of running for national office,” he would happily arrange it. Fifteen minutes later, Klein called back and said that Bloomberg certainly did.


Steinhardt left the dinner buzzing and spent weeks talking up the prospect of Bloomberg 2008 at various dinner parties. From returned to Washington dubious about Bloomberg’s presidential prospects, yet firm in one conclusion. “They’re serious about it,” he tells me. “I don’t necessarily think that they’re going to do it, but they clearly want to be ready if the opportunity is there.”

Until last week, when the furor over the Queens police shooting erupted, Michael Bloomberg, 64, was having a nearly perfect year. His approval numbers, which in 2003 fell to 24 percent, had been above 70 percent since January. By taking visible and voluble positions on issues from guns to immigration to stem-cell research, he’d started to carve out a national profile…

From Bloomberg’s City Hall coterie comes a consistent refrain: that their boss has emerged as more than a competent, steady, managerial steward; that he is, in the words of Deputy Mayor Dan Doctoroff, “a great, visionary mayor.” This sentiment is echoed, not surprisingly, by his friends. “There’s just no question,” says the investor Steve Rattner, “that he is the greatest mayor of New York since Fiorella La Guardia.”

Fast-forward to 2009. Bloomberg wisely chose to avoid a Presidential run, which would have led to his trampling by the Obama juggernaut. Returning his focus to NYC, he presided over a colossal Wall Street crash and an increasingly disillusioned electorate.

Bloomberg persuaded the City Council to change the law to allow him to seek a third term; New York City voters have twice rejected appeals to change this law in the past.

In the run-up to the election, Bloomberg’s campaign team warned him that the metrics had turned against him. Re-election, once seemingly inevitable, would be a brutal slog uphill.

A terrific piece in the New York Times today gives us the rundown:

In the days after the mayor had emerged, victorious, but badly bruised, from his fight to rewrite the city’s term limits law, Mr. Bloomberg and his three top deputies, Edward Skyler, Patricia E. Harris and Kevin Sheekey, gathered in the Staten Island room in City Hall and began to plot his campaign.

They warned him that it would be entirely different from his campaigns in 2001 and 2005. “This will be really hard,” one participant said.

Mr. Sheekey, the mayor’s political guru, urged him to quickly send a warning to potential challengers. He suggested recruiting a high-profile attack dog for the campaign and disclosing it to the press. The choice was obvious: Howard Wolfson, the combative former communications director for Hillary Rodham Clinton’s presidential run…

Mr. Sheekey pushed what he called the Powell Doctrine — a burst of overwhelming force that would discourage anybody who was even thinking about taking on the mayor.

This strategy succeeded in pushing Rep. Anthony Weiner from the race, a victory that in retrospect seems absolutely crucial.

Bloomberg’s ultimate opponent, Comptroller Bill Thompson Jr., ran a lackluster and inept campaign, surprising the Mayor’s reelection team with its almost complete inability to grab the attention of the local media:

The only obstacle remaining was Mr. Thompson. At Thompson campaign headquarters near Union Square, Mr. Bloomberg’s display of political might over the summer — he had spent $37 million by July 11 — was having its desired effect. By August, Mr. Thompson’s advertising team had stopped trying to track the mayor’s television and radio spending, standard practice in a campaign, telling colleagues it was too depressing. Anne Fenton, Mr. Thompson’s press secretary, told friends that she was intimidated by Mr. Wolfson.

At times, the Bloomberg campaign, waging what they proudly saw as a presidential-level operation, seemed puzzled by the poorly financed, sometimes loosely disciplined Thompson effort. The candidate’s daily schedule was curiously light, and easy opportunities to score political points were neglected.

Midway into the campaign, Mr. Thompson scheduled a publicity tour through a foreclosure-battered section of Queens, , setting off fears among Bloomberg advisers that the next day’s papers would be filled with articles suggesting that Mr. Bloomberg had neglected New York City’s neediest.

Team Bloomberg swung into action, dispatching a group of researchers to dig up Mr. Thompson’s ties to what they called an “anti-union developer” and $400,000 in campaign donations from real estate companies. They tapped out a 2,000-word e-mail message to the news media, titled “Thompson’s Rhetoric on Affordable Housing Doesn’t Match His Record” and prepared to hit the send button.

But to their astonishment, the Thompson campaign attracted almost no press to the event. The e-mail message never went out.

Despite the lack of a compelling alternative, some New Yorkers felt strongly that a “not-Bloomberg” vote was the way to go.

An epic rant by Gawker’s Alex Pareene is difficult to excerpt, because it hammers virtually every gripe that the city’s residents have with Bloomberg. Here are some of the highlights:

Tomorrow is Election Day! You will probably not vote, because there are no contested races for anything important in 90% of the nation. But if you are a New Yorker, we have one message: don’t vote for Michael Bloomberg.

You know those idiots who don’t know anything about politics but think it sounds smart to say “I am a social liberal and an economic conservative?” Bloomberg is the candidate for them, if they love a liberal nanny state and a conservative religious fervor for the eternal goodness of private enterprise.

For all the talk of Bloomberg the power-player who at least gets things done without worrying about the unions and special interests, he’s been unable to win any political battle with anyone he couldn’t literally buy off. Like Sheldon Silver, who (thankfully) killed the West Side Stadium and (annoyingly) ended all that “Congestion Pricing” talk. And those unions and special interests were just bought off, which worked fine back when the boom whose end Bloomberg never saw coming was in full swing.

And about that stadium: what the fuck was that? And the Olympics thing? After bitching about Giuliani’s disgraceful subsidizing of the fucking Yankees, Bloomberg both turns around completely on that particular issue and attempts to build the fucking Jets a stadium, so that New York could get an Olympics that it did not want. And that failed, and everyone forgot about it. Meanwhile: 40,000 people in shelters! Bloomberg could personally buy every single one of those people an apartment in a vacant Williamsburg luxury condo building and still have enough left over to bribe a City Council member into supporting his fifth term.


His record on housing, like his record on nearly everything having to do with the outer boroughs and poverty and human beings who make less than $100,000 a year, has been a ridiculous disgrace. His entire philosophy of development solving everything turned out to be precisely, 100% wrong, and suddenly the city itself was driving the real estate boom, driving up land prices to absurd levels across the boroughs and tearing down neighborhoods only to replace them with vacant lots and half-filled cheaply built hideous high-rises once the bottom fell out of the City Hall-inflated market. But hey, we got the High Line and 311! So you can sleep in that fancy park while you call 311 asking if there is room in a shelter because you can no longer afford your home.

Eight years into the Bloomberg administration, Ground Zero is a still a hole that everyone continues fighting about.


What he has done is Keep Us Safe by never once giving a shit about Civil Liberties. The cops stop and frisk thousands more people every year, your 4th Amendment rights do not apply in the Subway system, and expensive and completely ineffective new rings of cameras are going up across Manhattan.

Bloomberg deserves to be run out of town on an inadequately funded public rail line for the 2004 GOP convention alone. Remember that ridiculous farce? No, of course not, no one does, besides the thousands of people improperly spied on, arrested, harassed, and detained by the NYPD. All of this was completely illegal. No heads rolled.

One more special bonus factoid: New York leads the world in marijuana arrests! Specifically, marijuana arrests of black people!

And he is personally a jerk. He is a thin-skinned, unpleasant, sanctimonious asshole. His company is being sued for a culture of sexual discrimination that plaintiffs say Bloomberg himself contributed to. He is a tremendous dick to reporters whenever he gets cranky. He is fucking race-baiting with Rudy Giuliani again, because why not?

He has been a shitty mayor and he does not deserve the support of anyone who claims to be a liberal. Though what all of his most destructive missteps as mayor have in common is that they do not in any way upset or inconvenience the well-off self-professed liberals who support him. Besides maybe a couple Critical Mass riders arrested in illegal sweeps. (Though he sure does like bike lanes, so it’s a wash, right?)

We cannot encourage you to vote for the Democrat in the race, because even we still aren’t sure if we’ll go for him or the much more delightful Billy Talen. Just don’t fucking vote for Michael Bloomberg.

Despite all this, Bloomberg won a third term — in a squeaker.


His unlimited campaign funds couldn’t hurt: the mayor spent $157.27 per vote, as compared to Thompson’s $13.12.

His opposition was pretty pathetic, and he managed to keep Barack Obama from endorsing Thompson – a critical power play that probably saved his ass.

At the end of the day, Bloomberg retains a 70% approval rating; and yet a quarter of those who supported Bloomberg’s performance voted against him regardless.

Nevertheless, you don’t get bonus points for winning an election by a landslide – it’s winner-take-all in the USA, and Mike Bloomberg won.

bberg wins

Now, it’s very difficult to draw parallels between a city with 8 million residents and a city with 600,000 residents.

New York’s mayor rules over Manhattan and all the diverse outer boroughs, with all the complexity that entails. Boston’s mayor need not worry about nearby urban centers like Cambridge, Somerville and Quincy — he’s the lord of a relatively small fiefdom.

Still, on the day after election day, it’s interesting to observe the asymmetries between Boston’s “Mayor for Life” and the once-unstoppable NYC mayor who has to be wiping the sweat from his brow as he reflects on the narrow margin by which he won yesterday.

Bloomberg’s presidential dreams seem, in retrospect, to contain the seeds of his near-downfall: the hubris, ambition, and self-absorption that turned many New Yorkers against him on election day were all wrapped up in that lengthy flirtation with higher office.

Moreover, though, if Bloomberg wants to be the Richard Daley of New York City, he’ll need to develop the kind of organization that Menino has — on a larger scale, of course — and get his tentacles into every aspect of the city. Bloomberg will have to decide that his ambitions do not exceed the mayorship of NYC, and focus on maintaining and extending his power. There’s no doubt that a stronger opponent than Thompson would have cleaned his clock. Until Bloomberg has more than money on his side, he’ll remain extremely vulnerable, especially with the city in a weakened economic state.

When the voters feel that you’re on their side, that they know you and you know them — you can maintain power essentially forever.

As The Awl’s Choire points out this morning, that isn’t the case with Michael Bloomberg and many New Yorkers:

What people were voting against, in one way or another, was about being left behind. It was about financial inequity. What every New Yorker knows is that the City ran amok with the cost of housing, while home prices increased 77% between 2002 and 2007, and while, in 2007, the median household income in New York City was still only $48,631. The skew of the top 1% of earners very nearly did the City in—before the top 1% did itself in.

Bloomberg’s biggest problem with voters, and the reason that he actually very nearly lost yesterday, to a man who could barely run a campaign, is that people believe that the rich side with the rich—and yes, even when the rich also sponsor massive charitable giving. The Bloomberg bad bargaining policies of million-dollar real estate kickbacks for corporate real estate, and the administration’s failure to reach its goals in affordable housing, rankle with the middle class for a reason: these policies create larger inequity each year.

And now, we believe that the goals of the Bloomberg third term are to restore the City to the planned outcome of his first term, before the crash—a place of ever-growing division between rich and poor. His outrageous $100-million-plus campaign only served to reinforce the impression regarding who he really represents.

It’s up to Bloomberg to convince New Yorkers differently between now and 2012.

About Alpine McGregor
Just like you, man. I got the shotgun, you got the briefcase. All in the game, though, right?

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