After almost 20 years in office and with tantalizing prospects on his career horizons, Mayor Joseph P. Riley Jr.’s life reached an intersection in 1994. One path ran toward the governor’s mansion and a possible future on the national stage. The other circled back to Charleston.

So when his gubernatorial bid ended with a thud in that year’s Democratic primary, it signaled a new phase in the mayor’s political career. Shedding the aspirations to higher office he had worn so uncomfortably in his statewide campaign, Riley shifted his focus to the projects that would define the second half of his career: Expanding the city’s boundaries, finishing “The Joe” (Joseph P. Riley Jr. Park), completing the controversial S.C. State Aquarium, installing a modern drainage system, securing funding for the new Cooper River bridge, and so on.

By the time the first Charleston City Paper racks began cropping up around the peninsula in 1997, both the revitalized city and its 54-year-old mayor were running full throttle. Property values surged. National chains elbowed aside local merchants for retail space along King Street. Fine restaurants with celebrity chefs popped up across the city, seducing diners and noted critics from major publications. Political arguments abounded, but the Holy City was on a roll, and all sorts of things seemed possible.

So don’t take it personally, City Paper, but 15 years later, the nation’s longest-serving mayor doesn’t remember his first impression of your publication. He was just too busy.

Today the 69-year-old Riley is nine months into what he says will be his final term in office, and with a laundry list of things he wants to accomplish over the remaining three years, he’s busy now, too. As the soft-spoken mayor of a city known for its excruciatingly correct manners, it’s not exactly surprising that Riley has nothing critical to say about his relationship with the alt-weekly newspaper that has covered him for the past 15 years. But during an interview in his historic office overlooking Meeting Street, the mayor often sounded like someone put on the spot for an opinion about a distant acquaintance.

First memory of the City Paper?

“I just …” he begins, looking for words, then giving up the hunt. “It was here,” he shrugged.

Least-favorite City Paper cover story?

“I don’t have one,” he says. “And I don’t have a favorite one, either. First of all, I don’t keep bad memories. I don’t hold grudges. I have a very short memory in that regard.”

How has the paper changed?

“You know, I mean, I know there have been different reporters and all that,” the mayor says. “It seems like, you know, it’s got the same energy and, you know, liveliness and a little irreverence that it had at its birth. Fun, funny, serious…” His voice trails off.

In fairness to the mayor, asking Riley to comment about the City Paper is a bit like asking a middle-aged man to comment about a tattooed teenage girl while he’s sitting on a couch next to his wife. For better or for worse, Riley has been involved in a complicated, long-term relationship with The Post and Courier since well before he was elected mayor in 1975. Wherever the two wind up on any particular story, what remains is their common grounding in the same mid-20th-century Charleston culture.

In that context, the City Paper must have looked like a curious novelty when it arrived in 1997. But Riley did eventually find a place for the alt-weekly in his mental map of the city. “The City Paper was new, and my sense was that its readership was younger,” he says. “It took me a while to be aware of its readership. It’s a relatively new form of journalism. But I understood it was being read. It was available, and the audience was younger people, so it was important to me that I communicated to the City Paper, because [it was where some] of my constituents … were getting their news and information.”

And hopefully, it’s where they still do.

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