Can Sam Yoon Win?

By David S. Bernstein
February 11, 2009

Recent elections, as you may have heard, have been about change.

Newcomer Deval Patrick beat back the candidate of Beacon Hill and City Hall, Attorney General Tom Reilly, in 2006. And while the good old boys and girls of Massachusetts backed Hillary Clinton over Barack Obama two years later, it was Obama who walked away with the nomination, and ultimately the presidency.

But before them, although on a much smaller stage, Sam Yoon turned the trick here in Boston, stunning the insiders by winning an at-large city council seat in 2005 as a virtual unknown, beating three scions of powerful political families: John Connolly, Ed Flynn, and Patricia White.

Since then, Yoon – who declared himself a candidate for mayor earlier this week – has joined the grassroots “change” coalition of progressives, minorities, college students, and young professionals who gave Patrick and Obama victories in Boston and nationally – while Mayor Tom Menino in both cases backed the establishment candidates, only to be left behind by his own city.

This recent history, of change triumphing over establishment, has not dimmed the view of political oddsmakers, who say this year’s race remains Menino’s to lose.

Change in Washington, or even on Beacon Hill, is abstract - decided on TV and YouTube, based on feelings and platitudes. Mayor of Boston, on the other hand, is more nuts and bolts than hope and change. It is a powerful job affecting daily lives. It is not glamorous - and neither is Menino.

And Yoon, many observers point out, is no Patrick or Obama. He is a slight man, without a commanding stump presence. Born in Korea, he has no clear claim on the African-American voters whose tallies went overwhelmingly to Patrick and Obama.

The most daunting difference: neither Patrick nor Obama faced the difficult challenge of having to unseat an incumbent, as Yoon must do - that is, assuming, as nearly everyone does, that Menino intends to run for a fifth term. Yoon also faces at least two other challengers - one of whom, his fellow councilor Michael Flaherty, received more votes than Yoon in the last two at-large council elections, and starts with more money and better political organization.

So, can Yoon catch the “change” lightning in a bottle? After discussing that question with city politicos and observers for the past several weeks, the Phoenix has compiled this list of seven things that must happen to make his bid to become Mayor Yoon a reality.

Many are beyond the candidate’s control - as with Deval and Barack, Sam’s success will depend as much on the moment as the man.

1) YOON MUST RAISE THE MONEY Yoon’s supporters recognize that their candidate is well behind his two main rivals in the war-chest department, but argue that he can win despite having less campaign funding than his competitors because of the grassroots nature of his appeal. Perhaps, but even his top advisors realize that he can’t prevail without the capital to get out his message.

That probably means he’ll need at least $1.5 million - half to run the bulk of the campaign, and half for a sustained advertising presence in its final two or three weeks. Menino already has close to that amount banked, and will likely raise at least another million. Michael Flaherty has around $600,000, and a wide base of contributors.

Yoon has never raised anything close to that amount, and due to Massachusetts campaign-finance law, he cannot rely on a small group of wealthy benefactors. Individual donations are capped at a mere $500.

So he’ll have to hope that his campaign catches fire, whereupon Yoon might find himself flooded with small-dollar progressive contributors. (That hasn’t happened yet: a December push for online donations yielded little from that crowd.)

To spark his candidacy, he hopes to first tap into a national network of Asian-Americans, who may be eager to help elect the first Asian-American mayor of a major US city (and indeed one of the few major Asian-American politicians in any office). Yoon built up contacts during the Obama campaign, which sent him around the country to raise money from Asian-American communities in big cities. A “2009″ drive will seek to get $500 contributions from 2009 Asian-Americans, according to a source close to the Yoon campaign - an effort that, if successful, would yield a cool million.

But that potential brings political peril: Yoon’s opponents are wasting no time, and have already accused those donors of trying to buy the election from outside the state. Fair or not, attention on that source of funding could paint Yoon as a niche, racial candidate - the polar opposite of the post-racial image Patrick and Obama symbolize, one which Yoon wants to exploit.

2) HIS OPPONENTS MUST DRAG EACH OTHER INTO THE MUD To defeat Menino, a challenger must drive down the mayor’s sky-high favorability - which, according to polls, currently finds nearly three-quarters of Boston residents satisfied with their current leader. For Yoon to stand a chance, someone will have to start throwing haymakers.

Some local observers speculate that if Menino is forced into a real, down-in-the-dirt public campaign, things could go very badly for him. The mayor is not only considered a poor public speaker, he is notoriously thin-skinned - a trait made worse the longer he has been shielded from criticism. His insistence that things are going well sometimes makes him seem out of touch - particularly when defending clear missteps by the city, such as when he blamed college students and bar owners, rather than Boston police, after the fatal 2004 shooting of Victoria Snelgrove.

At least one political veteran thinks the odds are good that Menino could, under months of constant criticism, let loose with a public display of anger, petulance, or disdain - which could become his “macaca moment,” played endlessly on news outlets and YouTube, and demolishing his standing.

But then again, launching a harsh attack on a personally popular figure like Menino is a sure way to harm one’s own image.

Yoon’s savior, then, ironically, may be his City Council rival Flaherty, whose campaign strategy almost certainly includes plans for sustained, aggressive assaults on Menino. If effective, those attacks could leave voters looking for an alternative to both the attacker and his quarry - and finding Yoon standing above the fray, preaching his positive vision of the city’s future.

As one local operative says, it’s politics 101: A attacks B, and C wins the election.

But Yoon will still need to get his hands dirty, and engage in Menino-bashing, most locals agree. The criticisms of the current administration are more likely to take hold if they come from multiple voices. Also, by taking a few jabs himself, Yoon can demonstrate his own toughness, and prove his mettle for a job that all agree requires serious political-combat skills.

3) YOON MUST FIND HIS VOICE AND HIS MESSAGE Yoon is a slim little guy who sometimes seems lost in his own suit. He has glasses and a soft speaking voice. He seldom emotes. How can he possibly pick up the almost evangelical “change” mantle from Patrick and Obama without a commanding, inspiring speaking presence?

His supporters argue that, compared with the notoriously mumble-mouthed Menino and the impassive, monotone Flaherty, Yoon will seem positively stentorian. Maybe, but that’s not enough. Not for a relative unknown who needs to convince voters of his competence and leadership; and not for someone trying to personify hope and dynamic change. (And in fact, both Menino and Flaherty are often much better speakers than their caricatures would have us believe.)

Yoon needs to improve, and he very well could; it’s worth recalling that both Patrick and Obama took time to develop their stump skills. Patrick, a short man with a high voice, would hardly have been pegged as an obvious orator; nor would the gangly, wonky Obama.

Other city observers, including some fans of Yoon’s candidacy, say that Yoon is also hampered by the fact that, in an attempt to broaden his appeal, he too often plays it safe on issues. Without taking strong stands - and standing by them under withering political pressure - he fails to inspire, they say.

One prominent member of Boston’s minority community contrasts this aspect of Yoon’s political personality with Sheriff Andrea Cabral and former City Councilor Felix Arroyo, both thought of as “New Boston” candidates who rallied the same coalition of voters Yoon now seeks. Cabral and Arroyo, this observer says, won elections citywide by taking firm positions - alienating many, but impressing even more.

Yoon could find his voice and presence over the months to come - especially if he finds the right message to tout.

Like Patrick and Obama before him, Yoon must make people feel as though casting their vote for him is, in itself, an act of change - that we become the better society we wish to be by selecting a leader who embodies that better place. In this paradigm, Yoon has to convince voters he is the conduit to the New Boston of the 21st century.

That means moving away from the tribalism and factions that have long defined the city, and toward a collective sense of being Bostonian; that instead of neighborhoods, ethnicities, age groups, classes, and others fighting for attention and resources, we see our problems and concerns as all linked together.

That could be a powerfully positive vision. But, without specific policies and proposals, it can also seem abstract and removed from the city’s real, tough problems, including schools, jobs, public safety, and development. Yoon’s success will ride on his ability to couch the concrete issues of the day within the broader context of Old and New Boston.

4) THE CITY MUST CONFRONT ITS NEED FOR CHANGE Operatives with both Flaherty and Yoon claim that, beneath Menino’s positive poll numbers, you’ll find a desire for change in Boston. City residents aren’t really satisfied with the way things are being run, they argue - not with the schools, the crime, the dirtiness, the services, and the general lack of openness and responsiveness of city government. People seem to like Menino personally, but think he might be getting too old, too out-of-touch, or too stuck in his ways, these critics say.

If they’re wrong, of course, Menino will win re-election without breaking a sweat. But even if there is a kernel of truth to the theory, candidates will still need to do more than just talk about it to turn it into a ballot-box revolt.

For challengers to oust the incumbent, some political observers speculate, they will need to lay the seeds of doubt about Menino, and then have external events furnish the proof of his failings.

A good place for Yoon and Flaherty to start sharpening their knives will be during the upcoming budget process, which will see Menino proposing cuts to services that affect pretty much everybody, giving him very little cover for political attack.

But what really could hurt Menino is the kind of scandalous news story that puts faces and stories to city problems, rather than just dollars and cents.

Perhaps new revelations will come from the ongoing examination of pension abuse - triggered by reports of Boston Fire Department employees gaming the system. Or investigations into the Boston Police Department- one involving “Boom-Boom Room” partiers, and another involving drugs stolen from evidence lockers -could finally explode. Or, the federal corruption inquiry that has led to the arrests of former state senator Dianne Wilkerson and City Councilor Chuck Turner could expand to tarnish Menino appointees or friends. (Them’s the breaks when you’ve ruled the city for a decade and a half.)

But events that snap a city to attention are often entirely unpredictable. A stunning quadruple-homicide in December 2005 made the city aware of its rising violence - and made Menino appear out-of-touch for having dismissed the problem throughout that year’s mayoral campaign. And the tragic deaths of two firefighters in 2007 exposed the city’s failure to administer drug and alcohol tests - and made Menino appear weak in his dealings with the city’s unions.

5) MENINO’S AURA OF INVINCIBILITY MUST CRACK As long as people assume that Menino is unbeatable, he is unbeatable. Potential contributors, volunteers, and endorsers will stay huddled with the once and future mayor. News media, seeing no race, will not hype it.

In past elections, Menino has been able to remain in his bunker, safe with a large lead in the polls. He avoided almost all joint appearances with his 2005 challenger Maura Hennigan, for instance, and rarely responded to her criticisms.

In fact, Menino has not been forced to actually engage publicly in a campaign since 1993 - when, after replacing Ray Flynn as acting mayor, he beat a crowded field to capture his first full term.

This time, most observers believe, the challengers will be credible enough, and sufficiently funded, to draw attention and support. And some think that if his opponents’ support reaches a certain “tipping point,” to use Malcolm Gladwell’s phrase, others will feel safe expressing their own support for the challengers. That’s also when ordinary voters will start paying attention to the other candidates, and begin to seriously consider a post-Menino Boston.

6) FLAHERTY MUST TURN HIS SUPPORTERS AGAINST MENINO, NOT YOON In September, the three candidates (along with businessman Kevin McCrea, and anyone else who throws their hat into the ring) will square off in a preliminary election, with the top two vote-getters - presumably Menino and one challenger - going on to a head-to-head showdown in November.

One might think that all of the anti-incumbent voters will rally behind whichever challenger survives the preliminary. But that might very easily not be the case.

Flaherty and Yoon draw very different groups of supporters, as is evident in geographic breakdowns of votes in the past two City Council elections. In 2007, 55 percent of voters gave one of their four at-large votes to Flaherty, and 50 percent gave one to Yoon. But in half of the city’s 22 wards, the difference between them was more than 20 percentage points. Flaherty’s strongholds of support - South Boston, Charlestown, and even parts of Yoon’s home base of Dorchester - are dead zones for Yoon support.

Most of those Flaherty supporters, if asked to choose today, would probably vote Menino over Yoon.

By September, though, their support of Flaherty is likely to harden into real anti-Menino anger, as they listen to their candidate’s criticisms of the mayor, and as the mayor’s campaign attacks their hero.

People in Yoon’s campaign believe that anybody who votes against Menino in the preliminary - regardless of who they vote for - will vote against Menino in November, no matter who the other name is on the ballot.

But it is equally likely that, in the run-up to the preliminary, the Flaherty and Yoon campaigns will turn on each other, as they fight for the one golden ticket available to the main event.

If that happens, Yoon could win that spot on the November ballot, but lose many of those Flaherty supporters at the same time.

7) BOSTONIANS MUST CARE ENOUGH TO VOTE This, above all, may be the most important key to a Yoon victory. If the voter turnout looks like it did in the 2005 or 2007 municipal elections, Yoon probably has no chance. If it looks like it did in the 2006 gubernatorial or 2008 presidential election, however, all bets are off.

In 2007, with no mayoral election and few contested Council races, fewer than 50,000 Bostonians cast ballots. In 2005, with a weakly contested mayoral challenge, close to 100,000 did.

But in 2006, with Patrick on the ballot, turnout soared to more than 150,000. And in 2008, for Obama, 236,000 came to the polls.

The area with the biggest turnout swing - that is, where voters are most likely to vote in big elections and not small ones - are some of Yoon’s best pockets of support. They include Beacon Hill, Back Bay, Roxbury, and other parts of Dorchester.

Several political observers in the city put it bluntly: New Bostonians – including minorities and younger progressives - don’t vote in city elections. Yoon, as the New Boston candidate, is dead meat if that holds true in 2009.

On the other hand, as a Yoon advisor argues, Yoon has the most to gain from an increase in turnout. If Bostonians get excited about this election, Yoon could be the man for the moment - and could be mayor of Boston a year from now.