"The city leaders may look different someday, but will the desire to change the status quo shift?" counters Connolly. If not, he says, "We're never going to fulfill the New Boston promise."
A TOUGH SELL
Not all New Boston leaders are critical of Connolly — as often as not, those who know Connolly like him. A common expression they use, regardless of their own priorities, is "he gets it." I heard that from liberal political operatives and from reform-minded teachers. I heard it from black parents in Roxbury who attended one of Connolly's frequent education meetings, where he spent nearly two hours listening closely, taking copious notes, and asking keen questions.
And yet, many of the same people doubt that he can win New Bostonian voters in a mayoral race.
That is in large part due to the unavoidable facts of his birth. Among black and gay voters in particular, he occupies a no-man's land between the long-built trust in Menino on one side, and a promising crop of diverse young leaders on the other.
Connolly has also, through little fault of his own, been seen as the enemy by progressives and minorities, who remember and resent Connolly as the candidate who battled Yoon for a council seat in 2005, and whose 2007 victory ousted Felix Arroyo Sr.
That perception has been perpetuated as the younger Arroyo, an at-large councilor since 2009, has repeatedly sparred with Connolly; and Yoon, now living in Virginia, pointedly left Connolly out when he endorsed Pressley and Arroyo for re-election in 2011. Those tensions might have far more to do with political egos than policy, but still reinforce the notion that Connolly's on the wrong side.
It's clearly a source of frustration. "He's always had this view that he ought to be liked by white progressives and communities of color," says one supportive progressive activist, "when the truth was, he just wasn't going to get their votes."
But Connolly has also sometimes stepped on his own attempts to build an image as a change agent. He can come across as too ambitious, too calculating, and too openly political.
Many recall an incident, late in the 2007 city council campaign, when Connolly's campaign approved of postcards criticizing opponent Steve Murphy, sent through a third party to conceal their origin. It was quickly connected back to his campaign.
"That is the biggest mistake I've made in political life," Connolly says now. "It rightly raised questions about my integrity. . . . It was just plain wrong."
And education, while in theory a great issue to run on, also poses problems for Connolly. Many of Boston's black and Hispanic residents are wary of a white pol from West Roxbury talking about a return to neighborhood schools. Progressives associate education reform with charter schools and union-bashing.
"The issue is just so ripe in Boston," says an education-reform advocate, who supports Connolly but didn't want to be named discussing Menino and a potential challenger. Unfortunately, he concludes, "[Connolly] is not the ideal messenger."
If Connolly does run for mayor, he wouldn't need to win a majority of New Bostonian voters to beat Menino. But he would need to improve on the roughly 70-to-30 drubbing Flaherty took among them.
