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.
