Tom Menino had a big, fat, warm handshake. A hulking guy in his prime, he likely could have crushed your hand if he’d wanted to, but instead he just smothered it.

The first time I met the late mayor of Boston was in 1993. He was President of the Boston City Council at the time, and I covered city politics for a Boston newspaper. I introduced myself as we were walking out of city hall at the same time one day. He glanced down at me, shook my hand and said his name flatly, without even a hint of a smile. When I asked him a question about the city budget, he glared at me a minute, then barked, “I’ll get back to you.” Before I could give him a business card or a phone number, he’d turned and walked away.

A few days later, I received a package at the office that contained budget reports and a note from Menino: “What you were looking for…”

I gave him points for being responsive, but I didn’t think much of Menino initially. Watching him at city council meetings, I thought he was many of the things he ended up being known for: a mumbling, awkward speaker with a tongue that seemed too thick for his mouth, apparently incapable of extemporaneous communication in anything more complicated or lively than single-phrase sentences. Even in the media scrum after council meetings, Menino often teetered on the verge of syntactic collapse, the words so stuck in his pudgy craw that it seemed he might suddenly just give up altogether.

When he did manage to get his point across, it rarely seemed worth writing down. Menino’s comments were either obvious to the point of being needless to say—“The City of Boston has a budget for the schools,” he once told me, in response to a question about the number of school administrators making six-figure salaries—or focused on the minutiae to the point of being dull. In Menino, I saw the epitome of the urban neighborhood pol, a ham and egger who’d climbed as far as he was going to go.

How wrong I was.

In March of that year, President Bill Clinton appointed then-Boston Mayor Ray Flynn ambassador to the Vatican, setting off one of the most interesting mayoral races in Massachusetts history. By virtue of his council presidency, Menino enjoyed the title of acting mayor throughout the summer and fall of 1993, while he ran in a field crowded with candidates seeking to capitalize on Flynn’s unexpected departure. The high number of candidates drawn into the race—eight Democrats and one liberal Republican—reflected the widely held view that Menino didn’t have what it took to be mayor.

I spent time with all the candidates that year. In most cases, the people I met with appeared pretty much the same to me one on one as they had when I saw them speaking to large groups or on television. Menino was different—different from the other candidates, and very different from the Menino I was used to seeing in city council chambers or on the stump. While he was hardly eloquent, he was far more articulate when the cameras weren’t around. He had an obvious intelligence that didn’t come across in front of big crowds.

I remember my opinion of him changing dramatically during the course of an early morning car ride from Hyde Park, where Menino lived, to East Boston, where he spent a few hours campaigning. I sat in the back of a cavernous Crown Vic, Menino’s bulk sprawled across the passenger seat, the driver, an equally beefy man, gracefully navigating the city at top speed.

“Watch out, will ya!” Menino shouted every few blocks, muttering curses. “I gotta get there alive.”

As we drove, he quickly handicapped the race for me, explaining in blunt detail why none of his competitors could cobble together enough votes to beat him. Beyond the mathematics of the electoral landscape of a city he knew intimately, he offered quick insights into his competitors’ habits, noting, for example, which ones tended to be early risers and which ones made notable habits of strenuous physical activity.

Toward the end of the ride, I asked him about some particularly unflattering zinger Boston Herald columnist Howie Carr had tossed at him. Menino chuckled: “Howie being Howie. An entertainer. Who takes him seriously?” He turned to look at me—the only time during the ride—and said, “What the papers write matters, but not as much as you guys think.”

On the streets that morning, and whenever I saw him out campaigning after that, Menino was the same guy I’d seen in the Crown Vic. He wasn’t a gladhander. He seemed to know everyone. He liked to bust people’s chops a little bit. He stood outside trolley stops shaking hands just like other pols, but he wasn’t unctuous. He was a comfortable retail politician and when the election returns came in that November, the numbers matched almost perfectly Menino’s prediction months earlier on our ride to East Boston.

I only saw Menino’s first few years in office firsthand. When I told him I was coming to the Valley in 1995, he shook his head, smothered my hand and said, “I don’t know why you want to do that, but good luck to you.”

Since then, I have watched his story from afar. Following his amazing 20-year run as mayor helped keep me connected to Boston over the years. When I visit the city now with my teenaged daughter, I marvel at how it has changed since 1993.

Menino never did become a good public speaker, but even in an age that favored telegenic smooth-talkers, he could count on the voters to see him for who he really was.•