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Yoon or Flaherty

Who will win the chance to challenge Menino?
By DAVID S. BERNSTEIN  |  August 20, 2009


Boston voters will go to the polls in less than seven weeks to choose two candidates, out of the four now running, to face off against each other in November's mayoral election.

A statistician will tell you this preliminary round of voting can yield 24 possible outcomes. Anyone with an ounce of political savvy, however, will say that barring an earth-shattering electoral upset, Mayor Thomas Menino will come out on top and businessman and political maverick Kevin McCrea will finish last.

The Obama-Clinton Effect
Sam Yoon and Michael Flaherty have faced each other twice before — in at-large City Council elections, for which Bostonians could select both of them among their four votes. For a true head-to-head comparison, perhaps the 2008 presidential primary between Barack Obama and Hillary Clinton can serve as a surrogate. At least, Yoon might hope so: Obama bested Clinton here by 10,000 votes.

According to a Phoenix analysis of Boston election data, in 2007 Yoon received more votes than Flaherty in 90 percent of city precincts where Obama won a year later. Flaherty won 88 percent of precincts carried by Clinton.

The same pattern held for the 2006 gubernatorial primary, with Deval Patrick winning more than half the vote (in a three-way race against Tom Reilly and Chris Gabrieli) in almost all the precincts where Yoon topped Flaherty.

Yoon would be thrilled to repeat Obama and Patrick's success. But the same data reveals the reason why, in their own races, Flaherty has topped Yoon with room to spare. Turnout in the Obama-Yoon precincts declined far more — to less than a third, in many cases — than did the Clinton-Flaherty precincts for the 2007 city election. In Boston, Clinton voters are more likely than Obama voters to show up when local offices are on the line.

All eyes are therefore on City Councilors Michael Flaherty and Sam Yoon as they vie for the chance to unseat Menino, who with 16 years as Boston's political chief under his belt is the city's longest-serving mayor.

The final election may shape up to be the most serious challenge the incumbent has faced since winning election in 1993. But so far, at least, the race has been a sedate affair. Yoon and Flaherty focus their fire on Menino. They rarely take aim at each other: not on the stump, not in their literature, and not in interviews.

There are reasons for that, the primary one being that whoever survives the preliminary will need the others' voters in the general election. But that may be a difficult task since Flaherty and Yoon are chasing different types of voters for the September 22 contest. Flaherty is targeting the more traditional and reliable set that prefers him to Menino. Yoon, meanwhile, is after those elusive "New Boston" voters who turned out in droves for Barack Obama and Deval Patrick's elections, but who rarely show up for municipal contests.

Perhaps as the preliminary approaches the two will train their cannon fire on one another. But for now, their détente makes it difficult for a voter to decide which would be the more potent opponent in November.

Change vs. change
Flaherty and Yoon have much in common. They are only months apart in age, with the former recently turning 40 and the latter joining him in January. They hold the same job and similar progressive positions on major issues. On the stump, they criticize Menino for a similar litany of woes: lack of transparency; closed or rigged processes, particularly in city development; avoidance of responsibility; slow adoption of technology; and tolerance of mere adequacy, particularly in the city's schools.

There are differences, to be sure. Flaherty wants to reform the Boston Redevelopment Authority, while Yoon wants to shut it down. Flaherty has a more aggressive and comprehensive plan for reforming public schools. Yoon takes a harder line on reforming the police and fire departments (whose unions are major supporters of Flaherty).

More generally, Flaherty was born and raised in Southie — he's a Boston College and BC High double-Eagle with a Boston University law degree — which often gives his discussions of the city some depth. Yoon is a relative newcomer to Boston — not only born in South Korea but educated at Princeton before coming to Boston via Harvard's Kennedy School of Government — which makes it more compelling when he tells audiences that "we can't wait four more years" to put Boston on a new track.

But the real contrast in their rhetoric, and probably in fact, is similar to that which emerged between Obama and Hillary Clinton during their epic primary struggle. They, like Flaherty and Yoon, were striving to be the "change candidate" for primary voters who wanted to flush every trace of George W. Bush from the White House.

Obama embodied that spirit as an outsider, both in terms of race and political experience. Clinton, saddled with obvious "insider" experience, countered that she combined the desire for a new direction with the political skill and experience to make it happen.

Flaherty — a five-term councilor and son of an Irish Boston pol — is making the same argument when he frequently describes himself as a "bridge between old and new Boston."

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Related: Can Sam Yoon win?, Time for a big change, He's number three, More more >
  Topics: Talking Politics , Deval Patrick, Barack Obama, Sam Yoon,  More more >
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14 Comments / Add Comment


I'm glad you delved into some numbers here and I think you're right that Yoon is the much greater threat, in the end, than Menino.  He certainly has improved as a candidate and is really getting people excited out there.  That, matched with his command of the issues and frugal but sensible campaign spending has him pointed to the final.
Posted: August 12 2009 at 3:03 PM


Has anyone else noticed from Flaherty's ads that Flahertyl and Menino look alike! If voters are having trouble telling the different between Yoon and Flaherty, imagine what a Menino/Flaherty head-to-head would be. Flaherty looks like he's Menino's slightly younger (and skinnier) brother. Besides, Flaherty supported Menino forever until this election, pretty lame politicing.
Posted: August 12 2009 at 3:21 PM


Yoon's campaign is much more exciting- and talking about many more issues than Flaherty's. Flaherty is a life-long politician looking to go up the ladder. Yoon is putting it all on the line to implement overdue systematic change- like transparency (cough BRA cough), accountability, and open access to government. Flaherty is definitely the "safe" choice- just like Hillary Clinton was. And we all know how that turned out. People are done with politics as usual- and THAT'S why Yoon's going to win.
Posted: August 12 2009 at 3:27 PM


For all of the skepticism about Yoon's ability to beat Flaherty in the primary (which could be a fight), I think the important thing to remember is exactly what Bernstein said - Yoon has a much better chance of beating Menino in the end than Flaherty does. For people who just want to see Menino gone, that consideration should be a huge factor come September 22nd.

Posted: August 12 2009 at 3:28 PM


 I thought this was a thoughtful article regarding the Yoon vs. Flaherty mayoral race. As a Yoon supporter, I obviously agree with the author's closing sentiments that Yoon poses the more credible threat to Menino in the end. I've had a chance to observe Yoon close-up at campaign events and believe him to have the right stuff. Money is obviously the biggest obstacle to reaching out to voters but Yoon is making up for this by holding a series of town hall forums across Boston. He also appears to be making inroads to Menino's base in the minority community. He also has an enthusiastic band of volunteers, which is growing over time. I'm a political realist at heart, but if Boston voters really tune into this race, Yoon has an excellent shot at overtaking Flaherty come September 22nd.

Posted: August 12 2009 at 3:50 PM


If you watch the candidate's interviews with Jim Braude on NECN and listen to what Flaherty and Yoon have to say, it seems obvious who the better choice is. Flaherty is much more substantive and actually has a plan for what he wants to accomplish once he's in office. Yoon keeps saying that there needs to be change but is never very specific with exactly what he wants to implement if he is elected. The problem with not being part of the Boston political scene is that Yoon does not have as much of a grasp on what can and will work. 

Posted: August 12 2009 at 5:47 PM


Flaherty is Menino the part 2, he represents entrenched politics and Boston needs someone drastically different and ready to take on the tough job of turning this city around.

The man for the job is Sam Yoon, he's the one that is posing a serious threat to Flaherty and will be going up against Menino.


Posted: August 12 2009 at 9:17 PM


Mr. Flaherty does not have broad appeal in Boston. His base is South Boston and West Roxbury which is basically leaving him to fight for the same voters as Mayor Menino. If the communities of color and first-time voters come out for the primary, Mr. Yoon is going to beat Mr. Flaherty on September 22nd.
Posted: August 13 2009 at 12:40 AM


So let me see if I understand this article and post. Flaherty and Yoon are very close on issues, both are well educated, both are At Large Councilors..

Flaherty has topped the ticket the last 3 elections.. Has a large base in South Boston, Dorchester and West Roxbury, Solid support in all wards of the City, a large field operation, and significantly more money. (People are donating) 

Yoon has come in 2nd place city wide the last election. Has no base. Has no organization outside of the 5 people from Harvard Square (Cambridge). and has no money but I should vote for him?

Bottom line is you are asking people to vote because one candidate is Asian and the Other is Irish Anerican.. That is the argument? Put their records side by side and cover up the names and you have very similar pols. 

I have a hard time believing we are going to elect the next Mayor based on no substance but a theme of " He can win in Nov" 

Yoon is not going to beat Michael Flaherty in the Primary nor would he be able to beat Menino in a General. 

 David Berstein wants to keep Yoon afloat, bt even e knows it is over.











Posted: August 13 2009 at 7:15 AM


I don't see Yoon being able to bring out enough votes from the light-voting liberal wards. Also, compare Yoon and Flaherty on the issues. Flaherty has an impressive detailed white paper on the creative economy, a critical part of Boston's future. Yoon does not even mention this in his one-pager on housing and economic development. Flaherty also has solid ideas on energy, environment and green jobs. Yoon does not even address this but has a position on campaign finance reform. Typical out-of-touch pol. The money pinch has to hurt Yoon down the stretch.

Posted: August 13 2009 at 8:50 AM
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