Detractors compare Tom Menino to the late Richard J. Daley, who ruled Chicago for 21 years, the last of the big-city bosses. But Menino’s style also resembles that of William Donald Schaefer, a political free spirit who governed Baltimore for 16 years in the 1970s and ’80s, famous for phoning in fix-it orders for problems he spotted around the city.
With yesterday’s triumph, Menino steps into the history books in that rare company, bypassing in the process two local legends, James Michael Curley and Kevin Hagan White, to become the only Boston mayor to win a fifth four-year term in office. In a toxic political environment that imperiled incumbents all over the country, Menino was reelected by a comfortable margin in the toughest fight of his career.
Over the years, every mayor piles up enemies, the result of daily decisions that make people unhappy. With his long memory, Menino raised it to an art form. Those on the outs with the mayor knew it and sometimes felt it.
Menino once vowed to serve two terms in office. He’s just won his fifth - and presumably final - four years at City Hall. Now free of the demands of constituencies that kept him in office, will he rise above the moments of petty vindictiveness that undercut his many achievements? Will the “urban mechanic’’ aspire to be an urban architect or something greater as he works on his legacy?
If he is thinking grander thoughts, candidate Menino gave no inkling on his road to reelection.
Despite a constant pummeling by his opponents, Menino’s ratings in polls remained astronomically high. The outcome was never in doubt, much to the chagrin of those who have always underestimated him and never understood how this word-mangler from working-class Readville could be such a dominant force for so long.
In a series of debates and forums, Menino defended his administration vigorously and substantively as part of a positive campaign that will cost at least $2.4 million when all the bills are paid. He may not have been articulate, but he was sincere.
When he was sworn in as acting mayor more than 16 years ago, no one, not even Menino, could have imagined that he would one day become the virtual mayor for life.
How did he do it?
He showed up, which matters a lot in politics. From the day he took office, Menino spent most days on the move, in every neighborhood of the city, meeting his constituents and hearing their hopes and complaints. Like Schaefer in Baltimore, he often took action which produced results that were tangible.
On Menino’s watch, the city has not suffered the financial crises and social upheavals of previous administrations. Crime and public education, always major issues in big cities, have been managed under Menino.
No one has found the silver bullet to solve the problems of urban school systems, and Menino is no exception. But with much work yet to be done on the schools, many voters seem to have given him a pass on an issue on which he once urged voters to judge him harshly.
If Menino has a particular genius, it is that he understands Bostonians want to feel good about their neighborhood. That means visible police, antique street lights, and spruced-up business districts. From Brighton Square to Fields Corner, from Roslindale Village to Grove Hall in Roxbury, commercial districts have better stores and more restaurants and improved sidewalks and traffic controls.
For more than 16 years, Menino’s City Hall has paid attention to the details - zoning, liquor licensing, and congestion - that affect the quality of life where residents do much of their shopping and socializing.
His administration devoted disproportionately large shares of discretionary funds to projects in Roxbury, the long-neglected heart of the city’s African-American community.
On matters of race, gay rights, and other social issues, Menino has been consistently progressive. Hizzoner’s Daley-like political machine tightened his grip on power, but even at its most efficient, a great field organization is worth only a few percentage points in the final vote tally. Menino, however, has sturdy political infrastructure in virtually all 254 precincts. His army on the ground is of every hue and generation, and many are City Hall’s eyes in their neighborhoods.
Flaherty and Sam Yoon, the other city councilor who challenged Menino but did not survive the cut in the preliminary election, portrayed the Menino machine and its presence in the neighborhoods in sinister terms, like some sort of secret police reporting back on the naysayers who would join a “naughty list.’’
In the final, Flaherty and Yoon ran as an unofficial “team,’’ with Flaherty pledging to install Yoon as “deputy mayor’’ of an administration that would bring change to City Hall. It was clearly a gimmick but it may have produced a modest benefit for Flaherty, who, as a member of a sprawling political clan from South Boston, did not fit the image of an outsider or reformer.
Flaherty raised an impressive amount, spending about $1.3 million in his effort to unseat the entrenched incumbent. But he wasted a lot on consultants and an early campaign theme that said Menino was “good’’ for the city when he was elected in 1993 but Flaherty would be “better.’’
Flaherty’s problem was that his 10-year council record was thin on achievements. He was risk-averse and cautious; in many ways, a lot like Menino, only a generation younger.![]()



