MORE THAN ANY mayor in recent Boston history, Tom Menino has had a tenure shaped by serendipity. He was first vaulted into the position of acting mayor because he was in the right place (as president of the city council) at the right time (when then-mayor Ray Flynn was named US ambassador to the Vatican). Menino then adeptly leveraged his new station to beat a bevy of challengers in a special mayoral election. In 1997, he ran again and faced no opposition. And this time around, at-large councilor Peggy Davis-Mullen poses only the mildest of challenges to Menino in the November 6 general election.

In one respect, there’s nothing magical about Menino’s repeated electoral success: his mayoralty has coincided with the greatest economic boom this country has ever seen. Crime rates and unemployment figures have plummeted both nationally and locally since 1993. It’s easy to look unbeatable when you can point to statistics like these: in 1993, there were 98 murders in the city; in 2000, when prospective challengers considered running against Menino, there were just 40. In 1993, the unemployment rate was 7.2 percent; in 2000, it was 2.4.

But all that’s changed. The Boston Police Department reports that the city’s murder rate is on track to be the highest in at least five years. Already, this year has seen 21 more murders than last. And the city’s economy is in free fall. It began to falter this summer, but since September 11, when terrorists hijacked two planes out of Logan Airport and crashed them into the World Trade Center, things have truly started to collapse. Small landlords are seeing apartments go vacant — something unheard-of during the last five years. This is good news for renters, but it could lead to more bad news for the city as new property owners with empty units struggle to make hefty mortgage payments on residential housing purchased during the boom. As anyone familiar with the late-’80s real-estate market knows, this is a recipe for widespread foreclosures — which ultimately means lower property-tax receipts for the city. Meanwhile, the dramatic downturn in tourism means less revenue for city businesses: hotels, restaurants, and even taxi services.

At the same time, ongoing security concerns have put the city’s police and emergency workers on full alert around the clock — something that’s costing the city $100,000 per week, according to one source at City Hall. That means the city is facing $1.2 million in unanticipated costs over the course of the next year. And Massport, facing the loss of an estimated $50 million in revenue, has voted to cease the annual voluntary payments of $6 million to $12 million that it makes to the city in lieu of taxes.

"I can’t think of an economic dislocation that came as abruptly as this one," says Thomas O’Connor, a professor at Boston College and author, most recently, of The Hub: Boston Past and Present (Northeastern University Press, 2001). "It’s going to be a measure of Menino’s ingenuity as to how he handles this. I don’t know what he will do, but clearly this is his challenge. He’s going to be judged in the future on how he handles this."

For a politician with a legacy hanging in the balance, Menino doesn’t seem too worried. Exiting the Seaport Hotel last Monday after addressing the American Israel Public Affairs Committee, he said that tough times mean it’s time to "be more creative." He also points out that things weren’t so good in the city when he first became mayor: "When I took over in 1993, the economy was in the dump. There was a high unemployment rate. Revenues were down.... It’s a challenge. A challenge is when you do your best job."

The question is whether Menino — a man who’s coasted on luck for the last nine years — is up to it.

Menino’s achievements so far don’t exactly jump out at you the way his immediate predecessors’ do. Ray Flynn, who served as mayor from 1983 to 1993, can say he helped make the city’s neighborhoods stronger. As mayor, Flynn was more likely to be seen playing schoolyard basketball with a group of city youths than glad-handing downtown big shots. "When I took office as mayor of the city, Boston was divided racially," he recalls. "The people in the neighborhoods hated the people downtown. It was finger-pointing, division. I said the city will be governed by one set of rules, and that message hit home."

Kevin White, who served from 1967 to 1983, followed the examples set by John Hynes and John Collins to complete the revitalization of the city’s downtown. He can point to Quincy Market, reopened in 1976, not only as one of his most significant accomplishments, but also as a symbol of what the city can be.

But Menino has built, in particular, on positive aspects of Flynn’s legacy — especially in making Boston a less racially divided and more tolerant city. Perhaps because he is Italian-American — Boston’s first non-Irish mayor in a century — Menino has carefully put together a working coalition of the city’s various ethnic blocs. (Cynics would say he has had to do this to counteract the city’s Irish power structure.) Reaching out to all the residents of the city has been a strong feature of Menino’s governance — and it has paid handsome electoral dividends. Sure, Menino managed to win South Boston in last month’s preliminary election, but he also trounced Davis-Mullen in the African-American community (winning 88 percent of the vote in Ward 12, which includes parts of Roxbury and Dudley Square; 78 percent in Ward 17, which includes Codman Square; and almost 69 percent in Ward 14, which encompasses Grove Hall and Franklin Field), and he’s expected to do so again in November. "He’s been a leader who has battled to break down the walls of discrimination in this city," says Massachusetts senator Ted Kennedy.

During his first State of the City address, in 1994, Menino declared: "If 100 years from now they look back at my election, I hope what they see is the beginning of a century of inclusive politics." He’s made that beginning. The change in the city’s racial climate was noted in a September 9 Focus essay by Boston Globe national editor Kenneth J. Cooper, an African-American who recently returned to Boston after being away for 15 years. "This relaxation in Boston’s racial climate has astonished me," Cooper wrote. "It strikes me as a bigger and more fundamental change in the city’s character than, say, the Big Dig, the disappearance of Wang, Digital, and the Bank of Boston, or the decline of the secretive group of business elites known as the Vault."

Menino has also been the first mayor to recognize the power and promise of the city’s gay and lesbian community — not just in the South End, but across Boston, including Jamaica Plain. Today, we take it for granted that Menino supports domestic-partnership benefits and refuses to march in South Boston’s St. Patrick’s Day parade because it bans gay men and lesbians. But can we imagine Flynn — now the president of the Catholic Alliance — doing likewise? No fair analysis of Menino’s years as mayor could fail to recognize his achievements in this area.

"If Flynn reached out and said all neighborhoods are equal, Menino said all neighborhoods are open to everyone," says Democratic political consultant Michael Goldman. "The city became much more a city of oneness under Menino’s tenure than any other."

WBZ radio host David Brudnoy, a veteran politics-watcher, agrees: "I think the strengths of the Menino era have been enhanced by a strong economy itself, but also [by] him — a jovial inclusiveness that has made many people feel good."