Thomas Menino, after 20 years as the mayor of Boston, is expected later today to announce that he will not seek a sixth term. So what is the legacy of Boston’s first Italian-American mayor -- and its longest-serving?

Six months ago, the Mayor cut short his trip to Italy and entered Brigham and Women’s Hospital.  As the days dragged into weeks during his stay, for the first time in many years, Bostonians began to imagine what for the past twenty years seemed unimaginable: Boston without Mayor Menino.

On July 12, 1993, when then city councilor Menino became acting mayor, his political rivals campaigning for the job assumed that he was only acting like a mayor. His detractors dismissed him as inarticulate. He was even saddled with the nickname “Mumbles”.  But in November of 1993 he confounded his rivals by winning a full mayoral term outright.

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“You heard me say 100 times during the campaign, ‘I’m not a fancy talker’,” he said. In 1994. “This is my inaugural address. My first State of the City speech. But what I’d really like to do today is tell you a few simple things from the bottom of my heart – what this moment means in my own personal life. What this moment means for you, the people of Boston. What we can do together to get our city ready for a new century. Tomorrow, and next week, I will be laying out the specifics of my government reform initiatives.”

At the start of the Menino mayoral reign, most college freshmen today were not yet born; Boston’s skyline was not as full as it is today, and the Seaport District was an underused waterfront  -- not a thriving commercial neighborhood. Development has been the hallmark of Menino’s five terms in office. New skyscrapers, public housing, expanded bike paths, environmentally friendly building codes, and greener mass transit have all been a part of the mayor’s development agenda:  In a drive down Blue Hill Avenue with Boston Globe columnist Larry Harmon -- not long ago -- it was clear how the city’s neighborhoods have changed under Menino.

“When Menino came in, one of the first things he pledged was to help redevelop Blue Hill Avenue,” Harmon said. “And he really started right down by Dudley and Blue Hill and sort of made his way south, making this a better place. He’s worked very carefully with a lot of the community development corporations to build affordable housing here – good housing.”

Some projects, of course, never really took off, as evidenced by the massive hole in the ground in Downtown Crossing where Filenes used to be.  But other projects have brought hope to areas left behind including the Dudley Square. As mayor, Tom Menino has also dealt with the adverse effects of poverty, joblessness, and violence, and has worked, hands-on, with police, ministers, banking and housing officials and youth gang mediators to address these issues.

“I know, from my own life story, how important to a city the feeling of safety is,” Menino said in 1994. “I promise to dedicate my time as mayor of Boston not only to making you feel safe again, but to making your children feel safe again.”

In 2010 the drug-related robbery-murders of three adults and a two year old in Mattapan left the mayor visibly shaken.

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“Cowards hide,” he said at the time. “Let me tell you, Mattapan is strong, and will not let them hide.”

Boston during Menino’s 20 years in office has become a more diverse city … racially and class-wise.  The latter exemplified both by a burgeoning professional workforce and concomitantly by some of the highest housing rents in the nation. The Occupy Boston movement was a response to income inequality, and initially — in September 2011 — Menino was sympathetic.

But three months later he moved to remove the Occupy encampment in downtown Dewey Square:

“In the interest of public safety, ultimately, we had to act,” he said at the time. “We did so with patience and respect. I also want to recognize the people of Occupy Boston. They shined a much needed light – still needed -- on the growing economic inequality in this country.  And they also acted with restraint. I thank them for that.”

Tom Menino as mayor has also been entrusted with trying to rescue Boston from it’s bitter racial history -- still present in the air like the acrid smell of smoke. Luring the National Urban League conference to the city in 2011 was widely viewed as a correction of the city’s racial missteps or at least a step in the right direction in the view of others. But city councilor Charles Yancey said that Menino’s administration still falls short in some key areas.

“Boston city government has a long way to go to be truly reflective of the rich diversity that we have in the city of Boston,” Yancey said.

Many a political epitaph has been written about mayors who failed to respond adequately to natural disasters. Menino will not be remembered that way. During the Blizzard of February 2013, for example, he presided over the cleanup, though visibly weak.

“I’m happy to report the city, so far, has weathered the storm well,” he said. “No major power outages, no sever flooding. We still have a little way to go to get through the rest of the storm.”

But this was just the appearance of a strong presence. The mayor, as you can hear in his voice, was exhausted and pained. After all, he had spent two months in the hospital, with an initial diagnosis of blood clots and a severe respiratory infection, and a subsequent discovery of a fractured vertebra and type 2 diabetes. So in recent weeks there has been much speculation about whether one of the last big city mayor’s would run again. Just a few days ago on WGBH’s Greater Boston, the Mayor seemed to imply that he would:

“I love being in the neighborhoods of Boston, and you know, that gives me my energy, my vitality,” he told Rooney. “You know, I’ve been mayor for 20 years now, and it’s a very important part of my life.”

“I’m not finished yet,” he added. “There’s still a lot of things that need to be done in the city. We’ve made a lot of progress in education. But still we have work to do. I’m not going to ever say we’re finished till every kid gets a quality education in our city. Those are some of the things I care about, and education is the most important thing.”

And with a Boston poll showing the mayor with a nearly 75 percent approval rating, he would likely have been re-elected to a sixth term, pundits believe. But that same poll found Bostonians are concerned about the mayor’s health. And whatever spurred the mayor’s decision not to run, he leaves a legacy that has made him a star in the eyes of most Bostonians.