× Expand The election to succeed Mayor Dwight C. Jones is a year from now. Is it too soon to start speculating on who might replace him? Of course not. (Illustration by Victoria Borges)

Some time ago, I met a young politico for coffee at Lamplighter in Scott’s Addition, a once-forlorn industrial wasteland turned large-scale urban renewal project. That we were convening there to discuss next year’s mayoral race was a testament to the neighborhood’s — and city’s — trajectory.

The city is younger and more vibrant than ever, he reasoned; shouldn’t its leadership reflect the demographic changes that are contributing to its new sense of self?

“Richmond is looking for its Cory Booker,” he said before we parted, referring to the former mayor of Newark, New Jersey, who went on to the U.S. Senate.

Next November, the city will choose its third popularly elected mayor since the charter change of 2004. The first two contests landed L. Douglas Wilder and Dwight C. Jones on the second floor of City Hall, the former for four years of brashness, the latter for seven years of aloofness.

If the past year is any indication of which way things are trending, Jones’ successor will take office at a time when public confidence in City Hall is cratering thanks to inefficiency, poor management and a seeming inability to carry out basic tasks of governance. And there’s no transformative leader in sight. As depressing as that may be, it adds intrigue to what could shape up to be a competitive, and crowded, 2016 election.

At this stage of the game, with only two candidates declared as of this magazine’s deadline in mid-October and the rest of the field still shaping up, the current and former elected officials, City Hall insiders — including the young politico — and political observers interviewed for this story would only talk on background. But they’ve been busy scanning the political landscape, seeing who makes what move first, and their observations offer insight on how the hopefuls may fare.

Among the early favorites are Levar Stoney, the 34-year-old secretary of the commonwealth who has never held elected office; Michelle Mosby, the first African-American woman to be City Council president, whose rapid political ascent has not been without its hiccups; and Jon Baliles, the first-term councilman who may have a tough time appealing to constituents beyond his West End base.

The jockeying, which likely won’t begin in earnest until after this month’s state elections wrap up, gives rise to several questions: Whom will the business community throw its weight — and wallet — behind? Will the influence of Richmond’s churches on the race’s outcome be diminished in a younger, less African-American city? Which candidate can raise enough funds to rise above the presidential election chatter and connect with voters? Who is capable both of being an effective leader and a strong manager? Who has the chops and the connections across racial lines to carry five of the city’s nine districts?

What does the city need in a mayor?

The answer to that question is not what it was in 2008 or 2004. The city has undergone a resurgence in the last decade, one that is buoyed by a sense of good feeling long foreign to this place. Among longtime Richmonders, a true sense of surprise, bewilderment almost, is audible when they talk of what their city has become, or, as they say, how far it has come. September’s 2015 UCI Road World Championships showcased Richmond on the world stage — and it looked good. Twenty years ago, we wouldn’t have even qualified for an audition.

Crime is down. The city’s population, once depleted by white and middle-class flight, has surged since the millennium, as neighborhoods adjacent to downtown have gentrified. Developers have reimagined abandoned warehouses as apartments and condos in Shockoe Bottom, Manchester and Scott’s Addition. The city’s dining scene is eating up national accolades faster than you can say “Just the check, please.”

Virginia Commonwealth University’s ceaseless construction has breathed life into Broad Street west of Belvidere. East of there, a blossoming Arts District bustles on beautiful days. In two years, should all go as planned, the stretch will have a $54 million Bus Rapid Transit line connecting Willow Lawn to Rocketts Landing. Officials expect it to fuel more development, even if everyone isn’t sold on the idea.

But beneath that sparkling surface lie some serious foundational challenges.

Twenty-six percent of Richmond’s population lives below the poverty line, including 40 percent of its children. The city faces seemingly insurmountable odds in addressing this, though Jones, to his credit, has laid the groundwork for his successor to do so. Much of the city’s poverty is concentrated in monolithic public housing complexes in the East End. The city has come up with plans to redevelop some of those communities, a massive undertaking still in the early stages.

City schools, the subject of much budget wrangling in the last year, remain among the lowest performing in the state. Superintendent Dana Bedden has enjoyed great public support in his first two years on the job and seems to be moving things in the right direction despite not getting all the operational funding he wanted last year — City Council holds the school system’s purse strings — and hundreds of millions more in maintenance needed for the district’s school buildings. Bedden repeatedly has said that investing in schools is the answer to the city’s generational ills — whether next year’s field takes heed of his message may be key in the outcome.

“We really need to have someone who says, ‘This is the moment for education in Richmond,’ ” says the Rev. Benjamin Campbell, author of Richmond’s Unhealed History and a perennial watcher of city politics.

And then there’s City Hall.

City Council and the mayor’s administration seem to be on different planets at times. The finance department is a disaster, with several senior officials and an outside auditor jumping ship this calendar year. In early October, Richmond became the last locality in the state to submit its comprehensive annual financial report for 2014. It was 309 days late. City officials were warning that the 2015 report, due by year’s end, likely wouldn’t be completed on time, either.

Jones may leave office before we have the answers to some of the defining questions of his tenure: How will the city develop the coveted North Boulevard site? What will it do to acknowledge Shockoe Bottom’s slave-trading history? Where will the Flying Squirrels end up? Will Richmond ever have a freestanding children’s hospital? True regional public transportation? High-speed rail service?

The momentum is in the city’s favor, but who has what it takes to guide it, to build the bridge between the Richmond of murals, breweries, festivals and food, and the Richmond that languishes and is demanding equal access to opportunity?

Possible Contenders