Boston's longest-serving mayor seeks 5th term

BOSTON (AP) — For all of Boston's reputation for rough-and-tumble politics, mayors have enjoyed some decent job security over the last 60 years.

No one can attest to that better than Thomas M. Menino, who has been in office longer than any mayor in the city's history and is now seeking an unprecedented fifth consecutive four-year term. He's favored to win the nonpartisan race Tuesday despite facing his toughest re-election challenge to date from City Council President Michael F. Flaherty, who contends that after 16 1/2 years Boston is simply "Tom Menino-ed out."

Voters will decide if that's so, but it's been a long time since an incumbent mayor has been involuntarily removed. The last one was the roguish James Michael Curley, ousted by John Hynes in 1949 after a term that was interrupted by a five-month federal prison sentence for mail fraud.

Since then, Boston has known only five mayors: Hynes, John Collins, Kevin White, Raymond Flynn and Menino. All left office on their own volition: Flynn in March 1993 to become U.S. ambassador to the Vatican, a move that resulted in Menino becoming mayor by virtue of his position as city council president. He won the mayoral election that fall and three times after that, notwithstanding a famous lack of verbal eloquence that led detractors to nickname him "Mumbles Menino."

"Nobody has more energy than I have," insists Menino, 66, deflecting criticism that his administration has grown too complacent, too entrenched.

Flaherty, 40, received 24 percent of the vote in the Sept. 22 preliminary election, with Menino getting slightly over 50 percent.

The fact nearly half of voters cast ballots for someone other than Menino in the preliminary buoyed Flaherty, and led him to gamble on an unusual partnership with City Councilor Sam Yoon, who finished third with 21 percent. Flaherty has vowed to make Yoon, 39, his deputy mayor and the two have become inseparable on the campaign trail, running as a "ticket" though only Flaherty's name will appear on Tuesday's ballot.

Flaherty and Yoon understand they desperately need the support of older, established city residents, the most reliable bloc of voters in any municipal election, even as they reach out to college students and other young, progressive Bostonians. At night, they regularly visit bars and other places where younger people congregate, while also trying to get their message across on Twitter, Facebook and other social media.

Flaherty is a lifelong resident of South Boston, a neighborhood viewed during the city's busing crisis of the 1970s as a reclusive Irish-American enclave intolerant of outside forces. Though born of political expediency, Flaherty's teaming with Yoon, a community organizer of Korean descent, is a sign of how barriers in the city have fallen.

Menino's tenure has been marked by relatively little scandal, but a recent flap over deleted City Hall e-mails provided his opponent with an opening. A top mayoral aide, Michael Kineavy, took a leave of absence and the state attorney general's office announced it would investigate whether public records laws were violated.

Thousands of the e-mails were recovered and Menino had them posted on the city's Web site to bolster his contention that the deletions were accidental, not an attempt to hide something.

"We gave 10,000 e-mails online and nothing came out of those 10,000. Does that tell you a little story?" he asks.

Flaherty insists the e-mail flap is but one sign of a culture of arrogance at City Hall, an administration that feels it can do or say anything without being held accountable, and intimidate any dissenters.

"They have a naughty list," he said. If you speak out at community meetings .... or you try to rally your community or your civic organization to ask for more police, or to ask for better schools, you find yourself on the naughty list."

Lawrence DiCara, a Boston attorney and one-time city councilor, takes note of Flaherty's support among politically potent institutions such as the firefighters union, which has warred with Menino for years over pay, equipment and drug testing. But he's skeptical of Flaherty's ability to overcome the power of incumbency.

"If you're the incumbent mayor of Boston your visibility is approaching 100 percent," DiCara said. "The mayor is in the news all the time, and it's therefore very hard for someone to compete with that unless they have an awful lot of money."