Charleston Then & Now: How our city’s leaders see Charleston’s needs, priorities, and possibilities

It was a bright December day in 1975 when a spry 32-year-old Charleston native, a father of two young boys, took the oath of office on the steps of City Hall. The bells of St. Michael’s rang out with the deep tonal heft that comes from 220 years of bell ringing, chimes that had marked communal times of holiness, of warnings and war, of celebration. As he placed his hand on the family Bible held by his father, young Joseph P. Riley Jr. “looked out and saw citizens of all colors and walks of life,” he writes in his memoir to be published by Evening Post Books this spring.

Beneath Broad Street’s noon sunshine, Joe Riley became the city’s 60th mayor. It’s fitting that his inauguration was Charleston’s first to be held outdoors and in public, as over the next 40 years, Riley would do more than any individual in the city’s long history to create world-class outdoor public spaces like Waterfront Park, now named in his honor. About two years later, it would be from this same City Hall dais, under noonday sun with St. Michael’s bells peeling, that Mayor Riley would declare, as he would every year thereafter at the opening of Spoleto Festival USA, which he played a major role in bringing here: “When we are exposed to beauty and the quest for excellence…we can’t be comfortable with just getting by. Whether it’s in the public spaces or buildings we create, art challenges us to excel.”

From that inauguration day 50 years ago through his unprecedented 10 consecutive terms as mayor, this vulnerable, venerable, old port city became Riley’s artistic canvas for creating beauty. The work was never about just placemaking or constructing great buildings (the Gaillard Center and International African American Museum are but two landmark legacies imprinted with Riley’s aesthetic touch), but about how places and spaces shape us as human beings. As he stated at the dedication of Waterfront Park in 1990, words that are now inscribed at the park: “We give this park to the ages, all the ages to come…and we give this place most especially to those who need it most, to those for whom the burdens of life and its passages are so difficult to bear—burdens of body, mind, station, or lack of means. They most need a place of restful beauty…we give this park to lift the spirit, to light the mind, to warm the heart, and touch the soul.”

These lofty sentiments are those of a more mature Riley, one seasoned by early years in which Charleston faced issues quite different, and also many similar, to those that Mayor William Cogswell, Charleston’s 62nd mayor, is grappling with today. The outlook, then and now, is both window and mirror—one in which we look through and see how far the city has come and one in which we look in and see a reflection of concerns and themes present in 1975 and persistent in 2025.

Indeed, the two mayors themselves share a similar personal thread. Both were legislators in the South Carolina Statehouse before running for mayor. Both are native Charlestonians with long family histories here. Both have a track record in urban renewal and infill redevelopment, and Cogswell, who turns 50 this year—born during Riley’s first year in office—grew up a few houses down from the Rileys on Gibbes Street. “Our families have known each other for a long time, and Joe has been a big part of my career direction,” says Cogswell, who prior to becoming mayor worked with WECCO, a real estate investment and development company whose projects include the Cigar Factory, Garco Mill near North Charleston’s Park Circle, and Navy Yard Charleston. “I would come see him in this very office [in City Hall] and talk to him about projects I was working on. He was always patient and gave good advice. I admired him both as a mayor and as someone who was forward-thinking.” When Cogswell was applying to graduate school at Columbia University, Riley wrote him a letter of recommendation.

A WATERFRONT FOR ALL: The opening of Waterfront Park in 1990, after Hurricane Hugo, has been transformative for the city. The forthcoming The Cooper hotel, which will enjoy a vista similar to this aerial view, will continue the park’s path in front of the hotel, eventually connecting the waterfront to the South Carolina Aquarium and International African American Museum.

Charleston’s Main Street

In 1975, one of Riley’s first challenges was to breathe new life into King Street, which he tackled through masterminding the development of Charleston Place hotel. He recalls last-minute Christmas shopping that year, on the heels of his hard-fought campaign, and finding a ghost town—what had once been the city’s primary commercial artery was nearly desolate. “When I was romping down King Street as a 10-year-old, there were two department stores and other shops there. Now the buildings had deteriorated and many had been demolished over the last few years. Our revitalization plan told us this was where to start. The huge vacant lot needed to be robustly transformed. That vacant lot would come close to being my political graveyard. So close that a series of columns of brick samples constructed on the site were referred to as my tombstones,” Riley writes.

The young mayor’s vision for resurrecting that dead zone and transforming it into a 450-room luxury hotel, conference center, and retail hub met with significant opposition. “A lot of people, perhaps reasonably, wondered what did I know about restoring King Street or our central business district,” Riley recalls. For a decade he endured numerous setbacks, legal and political battles, and testy city council meetings, but finally in 1986, Charleston Place opened to great fanfare, and its success as the linchpin in revitalizing King Street is undisputed. Today, however, that feat comes at a cost.

Then, Riley was focused on increasing foot and business traffic along King Street. Now, Cogswell’s challenge (and Mayor John Tecklenburg’s before him) is subduing it, particularly along Upper King Street’s bustling—some would say, overrun—entertainment district. At a recent Traffic and Transportation Committee meeting, Cogswell heard the latest recommendation for extending rideshare pickup zones along Calhoun Street, as one effort to make the area safer for late-night revelers.

In the first two decades of Riley’s tenure, King Street was populated primarily by local businesses, boutiques, and antique stores; today smaller, local enterprises struggle to afford the high rents. Many unique-to-King Street draws, like Bob Ellis Shoes and Worthwhile, have either closed or relocated, while national retail brands proliferate, diminishing the shopping district’s Charleston-specific flavor. “King Street is the heartbeat of Charleston. It serves as both the bellwether and economic powerhouse driving nearly $2 billion annually to the city and state,” says Rhett Outten, principal and marketing director of Croghan’s Jewel Box, a King Street stalwart for more than a century. “Mayor Cogswell’s efforts to elevate the King Street experience are not just revitalizing a street but uplifting our whole community.”

Charleston’s Waterfront

The aforementioned Waterfront Park, a “Central Park-like” component of what Cogswell calls Riley’s “forward-thinking” urban vision, offers yet another mirror in which the Charleston of 1975 reflects that of 2025. Soon after taking office, Riley began imagining how the Cooper River waterfront north of the Battery could become something more than a “hardscrabble, 12-acre patch that was little more than free parking for Broad Street lawyers,” says Capers Barr, Riley’s longtime friend, adviser, and former law partner. The site was an eyesore, plagued with environmental problems, according to the City’s 1974 Historic Preservation Plan. “Derelict piers, rotted pilings, and weed-grown fill mar the appearance of an otherwise beautiful river,” the plan noted. Riley envisioned something greater, and in 1979 announced his plans for a park of “almost national significance.”

With signature tenacity, Riley prevailed against a developer who had proposed a high-density development that would in effect block out the water’s edge, denying the public access and view of the river. Since its completion in 1990, the Joseph P. Riley Waterfront Park, with its iconic Pineapple Fountain, shady oaks, and crushed-stone paths (the details of which the mayor was particularly attuned to, sampling a dozen mock-ups of gravel mixes for the perfect grade) has earned that national significance and recognition.

Today, the waterfront parallel for Mayor Cogswell relates to Union Pier, a 70-acre tract adjacent to Waterfront Park and owned by the State Ports Authority, which intends to sell the land to local businessman Ben Navarro after a failed first agreement with Los Angeles-based real estate developer Lowe. Lowe’s proposed designs, which the city rejected in 2023, included a high-density mix of high-rise condominiums, office space, and retail shops with a few green spaces. Intense backlash from the public and conservation groups argued that these plans fell short on opening the waterfront back to the public and instead prioritized profit over community enhancement.

In response to this extensive feedback, the City of Charleston and South Carolina Ports agreed in June 2023 to extend the planning timeline for Union Pier and to engage the Joseph P. Riley Jr. Center for Livable Communities at the College of Charleston to facilitate a community-engaged process. Here again, the then/now echoes of Riley are apparent, as Cogswell also notes. “We have an incredible opportunity with Union Pier to create a space like Waterfront Park, like White Point Gardens and Governors Park on Daniel Island—some of our other incredible public waterfront places. But this could be one of the best, if not the best,” he says. “My hope and plan is that [Union Pier development] will include modern resiliency and innovative initiatives that will help stormwater flooding on the whole eastern side of the peninsula. It could be an extension of the Battery. You know, really give it a major jump-start coming up the eastern side of downtown.”

(Left) Mayor Riley at his desk overlooking Washington Square in 2014; (Right) At a press conference with the Army Corps of Engineers, Cogswell discusses the completion of a portion of the Battery upgrades and reinforcement. 

Physical & Spiritual

In Cogswell’s view, the Charleston of 2025 must address two primary issues, both of which could be considered what many have dubbed “existential” challenges—those that are integral to “sustaining who and what we are, to preserving our character, which is what people love about Charleston,” Cogswell says. “I truly believe we are a very unique place.” But to stay that way, addressing these two is imperative. The first challenge is physical, he asserts, and one that is well known to everyone: flooding.

Charleston’s flooding problems are far from new, and in fact may date back to early colonial times, as creeks and marshes began to be filled as the city grew. In more recent years, measures to address flooding, protect the low-lying peninsula in the face of climate change and sea-level rise, and to improve Charleston’s resiliency were top priorities throughout former mayor Tecklenburg’s two terms, during which the Army Corps of Engineers proposed building a seawall as one protective measure. Numerous other drainage improvement projects have been ongoing. Meanwhile, the serious impacts of flooding, even on sunny days, have risen even higher than the water, with Charleston experiencing a 400-percent increase in days of flooding in 2020 as compared to 2000. “We need to look at how to protect the city, but do it in a way that’s a marriage of form and function,” says Cogswell. This echoes the recommendations from the Dutch Dialogues, and those of Dale Morris, Charleston’s former chief resilience officer, who oversaw flooding strategy before his resignation this past June. His departure caused many to express concern.

Currently, the city is moving forward with the Army Corps’ perimeter protection plan, though Cogswell, who was critical of the idea during his campaign, is careful about verbiage. “It’s not a seawall,” he insists. “It’s an extension of the Battery, which is infrastructure dating back to the mid-19th century for the purpose of keeping storm surge at bay.” Cogswell’s administration recently signed a memorandum of understanding with the Army Corps to explore design options before any work officially begins. An engineering firm has been hired to do preliminary work, beginning on the west side of the peninsula.

The city’s second fundamental challenge is more spiritual, in that it “goes to the heart of who and what we are,” Cogswell says of Charleston’s affordability crisis. “It’s wonderful to have so many people moving here. I’m a big believer in welcoming people, businesses, artists, and entrepreneurs—that’s who we’ve always been as a hospitable city. I don’t want to close the gates,” he adds, “but we need to make sure Charleston’s character is protected, not diluted. Much of that character is at risk due to affordability issues.” The Mayor intends to purchase two empty lots on Morrison Drive from Charleston County, where he plans on adding 500 units to the city’s affordable housing stock as one of several ongoing initiatives. “We also need to address affordability as a regional issue, working with our neighboring municipalities,” he says. “This isn’t just a Charleston issue.”

Nor, like flooding, is it a new one. Joe Riley tackled affordability 50 years ago, bringing his ever-keen eye toward creating a more beautiful city as he problem solved. Instead of building standard, bland, and poorly constructed public housing concentrated in relatively undesirable areas, Riley introduced the concept of scattered-site affordable housing, mixed within neighborhoods. “A few apartments here, a few there; each building designed to blend in with the neighborhood so that you wouldn’t know which building is public housing and which isn’t. Think what we can do,” he told his Housing Authority chief. “The child of public housing would walk out the front door and see across the street a business owner, or next door a medical student, or around the corner the neighborhood minister, and in the next block the retired school principal. The retired school principal would have a new child in the neighborhood that she could keep an eye on, perhaps babysit every now and then, maybe read a few books to him along with the thousands of invisible beams of affection and support that are possible.”

Then and now, Charleston’s leaders have embraced challenges and opportunities with creativity and a commitment to improving the city’s livability for all. Riley, one of the nation’s most revered civic leaders, earned that acclaim thanks to 40 years of experience, trial and error, and an unwavering belief in the power of the public realm. “Every citizen in their town or city has access to and owns the public realm, and every time it is made more beautiful, each person’s citizenship has been enhanced—a beautiful, healthy, restored city is a treasure for every citizen,” he writes. Cogswell is entering only his second year in office, but does so grounded in a strong sense of his mentor’s wisdom and an optimism about the changing of the guard not only in the City of Charleston, but in Summerville and North Charleston, both of which also have new mayors, as well as new faces on Charleston County Council.

“Bringing in new perspectives can be exciting,” he says. “It’s an opportunity to think through how you operate and who you are.” Charleston has changed a lot over the last 50 years, he notes, but what hasn’t changed is the desire “to celebrate our culture and our character. And I’m not talking about doing that just for visitors, but for the people that live here,” Cogswell adds. “To remind people of how wonderful a place this is, and that we’re all in this together.”