In the running for Boston mayoral position: Martin Walsh and John Connolly. (Photo: Bostinno)

The last time this column visited Boston was on the eve of the September 24 preliminary mayoral election.  On that Tuesday, the 12-candidate field was whittled down to just two: Martin Walsh and John Connolly.  This Tuesday, November 5, Boston voters will decide which of these two Irish Americans will take the reins at City Hall from five-term incumbent, Thomas Menino.

That each finalist is a white Irish Catholic male is something that came as a surprise to many observers. They believed that this was the election in which a now minority majority city with tens of thousands of transplants who’ve moved in and displaced many long time residents – a “New Boston” – could select a woman or a person of color to be its next mayor.

These observers were proven wrong for two reasons, however, in the preliminary election.  First, as has been detailed forensically by former Boston City Councilor, Larry DiCara, and Northeastern University doctoral student, James Sutherland,
this “New Boston” did not emerge at the polls. Turnout was, by far, heaviest in the traditionally voter-rich neighborhoods. Moreover, multiple candidates of color divvied up the minority vote.

Second, Connolly and Walsh represent a different breed of Boston Irish politician. Each is a genuine progressive. For decades, certain assumptions were made about the city’s politicians of Irish descent. A lot of this goes back to the tragic era of forced busing when Boston’s then mainly Irish American politicians rightly pointed out what an extraordinary injustice it was. Some went way too far, and played to people’s worst fears and darkest instincts. The stereotype of the hard-bitten, conservative, racist Boston Irish politician persisted – often unfairly, in my view – for some time.

Conversely, Walsh and Connolly have aggressively courted communities of color and have touted their progressive bona fides from the outset of the campaign. Both candidates, and Connolly in particular, have focused on education and on the need for Boston’s schools to improve and to adapt to meet the needs of students for whom English is not a first language and who live with parents who don’t speak any English.  They believe equally that Boston’s police and fire department personnel need to look more like the city they serve and that the profound sense of alienation so many young people of color feel must be addressed.

Although the candidates are relatively similar when it comes to ideology, they are two very different people with divergent life experiences. John Connolly is the son of a former Massachusetts Secretary of State and Massachusetts District Court Judge. He went to the prestigious Roxbury Latin School, Harvard College and Boston College Law School. He worked as a teacher in inner city schools and as a corporate lawyer before he was elected to the Boston City Council in 2007.

Martin Walsh is the son of immigrants from Connemara, Co. Galway. He followed his father into the building trades after he finished high school. He battled alcoholism before turning his life around. He was elected a Massachusetts state representative in 1997 and rose to become a high ranking labor union official at the same time. He ultimately went back to college and received a degree in Social Science from Boston College. Walsh has even earned more money than Connolly in recent years, as the latter’s campaign operatives have stated repeatedly.

While neither Walsh’s nor Connolly’s background necessarily means that he would make a better or a worse mayor, there is no question that their life stories have shaped the contours of the race since they made it through the preliminary. 

Walsh’s union credentials have engendered what may be an unprecedented effort from organized labor on his behalf. Unions and union members from the city, the state and throughout the country have provided him with a substantial campaign war chest and a huge army of foot soldiers working the phones and pounding the pavement. Connolly continually references his time as a teacher and the fact that he is a Boston public school parent, and he has enthusiastic support from parents of school age children in the city.

Geographically, Connolly is from the western part of the city and has a base in its high voting wards in the West Roxbury, Roslindale and Hyde Park neighborhoods. Walsh is from Dorchester, Boston’s most populous neighborhood, and is running very well there and in neighboring South Boston. The two candidates will own their home turf. And each has pockets of strength in other neighborhoods like Charlestown, Jamaica Plain and Mission Hill.

The two loose groupings who may tell the tale in the end on Tuesday are voters of color and newer city residents. The latter group tend to be more affluent and are more likely to support Connolly, with whose professional pedigree and even his Boston accent-free speech pattern they are more likely to identify.  Connolly’s mantra in the campaign’s closing days is that Walsh’s labor ties mean that he cannot be trusted to stand up for taxpayers against public employee and other unions and will endanger the city’s finances. This is clearly aimed, at least in part, at this group. The difficulty for Connolly, as DiCara and Sutherland have established, is that new Bostonians did not engage in the preliminary and are unlikely to turn out in much higher numbers on Tuesday.

Thus, it seems probable that voters of color will decide the outcome. And the key factor here is that Walsh has collected endorsements from all of the former mayoral candidates of color who have expressed a preference, including third place finisher and the only female candidate, former state representative and Menino administration official, Charlotte Golar Richie. He has also amassed a myriad of endorsements from other minority leaders.

Maybe most notably, and definitely most symbolically, Walsh has garnered a vote of confidence from African American elder statesman, Mel King, a former state representative and a Boston mayoral finalist in 1983 when Ray Flynn, the last Boston Irish mayor, was elected.  Endorsements don’t vote, but these politicians are working hard for Walsh. The most recent poll shows that their backers are breaking decisively for him. In addition to his having earned endorsements from people they trust, I suspect voters of color are moving to Walsh because his life story resonates more powerfully with them than Connolly’s.

I believe their votes will put Martin Walsh over the top and make him Boston’s next mayor. The polls indicate that there is a pronounced surge for Walsh, yet the race remains very tight. It will all come down to turnout. And I just don’t think Connolly has anywhere near the get-out-the-vote operation Walsh does. At any rate, all will become clear late on Tuesday. A long night in Galway lies ahead.