OF COURSE, it’s easy to keep a city feeling good when crime rates are low and everyone has a job. But how will he fare in the new economic climate? Particularly as he begins his all-but-guaranteed third term — as did White and Flynn before him — with a cockiness bordering on arrogance? He’s already drawing fire for his decision to debate Davis-Mullen just once. The decision prompted Boston Globe columnist Adrian Walker to charge that Menino’s message was this: " It’s my city, and I’ll do as I please. " He’s yet to make a formal announcement of his candidacy for re-election, the staple of any meaningful political campaign. And although Menino backers say the low-key approach is justified in light of the September 11 tragedy, that doesn’t explain why he didn’t see fit to announce his candidacy before September 11.

Aside from the arrogance factor, the biggest adjustments Menino will have to make concern the development agenda he’s mapped out for the city. His legacy will undoubtedly hinge on the fate of a number of pet projects: the waterfront and the convention center, the new ballpark for the Red Sox, and the Millennium Place complex near Chinatown (most of which have been discussed at length in these pages; see www.bostonphoenix.com and click on " News and Features, " then " Politics " ). No matter what anyone thinks of the merit of these projects — particularly the convention center and the ballpark — it must be obvious by now that the convention center is in serious trouble and the July 2000 plan that had the city forking over $140 million to buy and prepare land for the Red Sox is dead and buried. It is hard to imagine that Menino will continue to push for the new ballpark in the midst of fiscal slowdown and round-the-clock concentration on Boston’s security. Development must take a back seat now — or be abandoned altogether. There’s further danger, too. With an economic downturn upon us, the city risks seeing the site of the new Ritz-Carlton at the cusp of Chinatown and downtown fall back into ’80s-era seediness.

But Menino can’t ignore development completely — especially on the waterfront. He has set up a structure for waterfront development, and a plan is in place for the Pritzker family to build a massive project there. The waterfront is the part of the city most likely to bear Menino’s personal imprint — just as Quincy Market bears former mayor Kevin White’s. " This is a changing topography which is going to make the entire city look different, " says Boston College’s O’Connor. " How he deals with this area is going to be some measure of his influence as mayor. "

But he’ll be working on development in a dramatically changed economic climate. Even in the best of times, Menino was unable to deal with Boston’s affordable-housing crisis — a crisis that’s seen a steady stream of average- and low-income workers priced out of the city during his tenure. The National Low Income Housing Coalition reports that a minimum-wage worker would have to work at least two jobs to pay for a two-bedroom apartment in Boston. And even if the price of higher-cost housing is falling — as suggested by an October 11 article in the Globe — low-wage workers are not yet reaping the benefits. This failure is particularly damning when contrasted with Menino’s strenuous backing — both politically and economically — of the convention center and a new ballpark. (Menino says he will take up the housing issue on a national level when he becomes president of the US Conference of Mayors in June.)

In the meantime, the city school system faces long-standing problems. In the same 1994 speech in which the mayor declared that his tenure would be marked by " inclusive politics, " Menino vowed to put education at the center of his agenda. To that end, he made full use of the school-committee reforms initiated under Flynn, and engineered a committee friendly to his plans. Then he selected Thomas Payzant, a nationally recognized educational leader, as Boston’s new superintendent of schools. And guess what? Education in the city, generally, has not improved. The Boston Globe reported on October 15 that despite improvements in standardized-test scores, school spending, and college-attendance rates, the dropout rate remains high, and weapons and crimes are increasingly reported in the schools.

Of course, even the most energetic city mayor would have difficulty bringing a school system dominated by inner-city youth and recent immigrants within his or her sphere of influence. The mayor can prod, select, persuade, and cajole all he wants, but the problems that undermine urban education are broad, societal, systemic. Still, the mayor could have done more — and still can — to get the teachers’ union to agree to concessions that might make reform possible. And even the minimal symbolic progress Menino made in education could evaporate if the worsening economy begins to drain the city’s coffers in any serious way.

Menino seems to be aware of the limits on his education effort. " It’s a deeper issue. It’s a societal issue, " he says, adding that he will address it further from his post as president of the mayors’ conference.

THE SCARIEST scenario for Menino would be if Boston’s downward spiral — and the country’s — turned out to be the start of the kind of seismic shift not seen since World War II. Previous Boston mayors — Hynes, Collins, White, Flynn — all had to deal with periodic downturns and recessions, but none faced a massive reordering of the city’s economy. In recent years, Boston has grown dependent on the interconnectedness of the global economy, in which Americans zigzag all over the world and international businesspeople and tourists visit Boston for a host of reasons — to receive world-class medical treatment, to visit their children in college, to enjoy the city’s sights and sounds. If President George Bush’s war on terrorism really involves a long struggle with threatened retaliatory attacks, the prosperity Boston has enjoyed in recent years could be on its way out.

Boston has not faced a situation like that since the era of James Michael Curley, who served as mayor for much of the first portion of the 20th century. Curley enjoyed unprecedented success, but in his final term he had to face the convergence of two ugly trends. When World War II ended, Boston lost revenue (as a sailor’s town, it had thrived during the war) and saw industrial jobs move from the city to the suburbs and to other parts of the country, marking a permanent shift in the city’s economy. At the same time, federal funds began to replace the sources of patronage that had been the bread and butter of his own career. Soon local congressmen became the go-to people, outpacing the mayor — think of representatives elected in more recent times, such as John F. Kennedy, Tip O’Neill, and Joe Moakley. This change left Curley with no base and, ultimately, no job.

Menino, like Curley before him, is entirely committed to the city. But the problem with keeping the same job in politics for too long is that the things that worked for so long sometimes go wrong. Good luck turns bad. And when somebody gets on the wrong side of a turnaround — economic or karmic — look out.

Seth Gitell can be reached at sgitell[a]phx.com