Nashville Mayor-elect Freddie O’Connell addressing supporters on Aug. 3 2023. (Photo: John Partipilo)

It didn’t take long for Nashville mayor-elect Freddie O’Connell to learn that even the best-laid plans can go astray. 

O’Connell, a former chair of Metro Nashville Transit Authority, scored his first electoral victory to the Metro Nashville Council in 2015, thinking he was joining at the perfect time. Nashville had just elected Megan Barry as mayor. She would go on to propose one of the most ambitious public transit plans in the city’s history, only for it to fail spectacularly.

“I assumed I’d have four to eight years with a dynamic mayor who was going to try and do something big and important on transit,” O’Connell said. “I got three [mayors] instead, and the final one turned out to be, apparently, unwilling to invest in transit.”

On Sept. 14 Nashville elected O’Connell as its 10th mayor. He defeated former Republican strategist Alice Rolli by a nearly 2-1 margin. 

O’Connell’s rise – from Montgomery Bell Academy and Brown University graduate to technology entrepreneur and civic organizer, to city councilman and finally, mayor — makes sense on paper. But those who know him say his path wasn’t preordained.

“I don’t think he ever turned in his nominating paperwork for his first term of city council thinking that one day he’d run for mayor,” said O’Connell’s brother Sam. “It’s been a progression. Not with zero planning, but thoughtful deliberation along the way.”

To better understand O’Connell, the Lookout spent the last weeks of the election talking to his family, friends, and political and business associates, and for two mornings followed the man who in two weeks will become Nashville’s next mayor at 46 years old. 

Those who know O’Connell affectionately refer to him as “wonky” or “nerdy,” whose magic strength is maintaining friendships and genuinely enjoying retail politics. They regale stories of him showing up at obscure neighborhood meetings, hosting Thanksgiving bashes that run deep into the night, and a willingness to talk at all hours because it seems like he doesn’t sleep.

For most of the election, O’Connell ran an anti-establishment, neighborhood-centric campaign with a relatively small budget. For the first eight months of his campaign he had only Marjorie Pomeroy-Wallace and Scott Dietz as paid staff members.  It was during the runoff this changed, as the business community’s money united behind him – citing O’Connell’s pragmatism – and he produced a handful of attacks toward Rolli.

On the campaign trail, the race began to pivot in O’Connell’s favor during Nashville’s hectic forum circuit, where his knowledge of city issues and plans to address transit and housing problems separated him from a crowded field.

Transit is by no means the only issue O’Connell cares about, but it certainly animates him, linking much of his organizing and public policy background as a former president of Walk Bike Nashville with his time on the city council and transit authority board.

After graduating from college in 2000, O’Connell spent his first 12 years back in Nashville without a car, traveling the auto-dependent city by foot, bike or bus. If absolutely necessary, he’d use his partner Whitney Boon’s.

But when friends finally talked him into buying a vehicle, he won an eBay auction for Blade Runner actress Daryl Hannah’s 1983 biodiesel-powered Chevrolet El Camino. 

“He fought and fought and fought the idea of owning a car,” said Thomas Conner, a friend of O’Connell who’s known him since he hired the latter in 1997 at a tech startup he co-founded called Telalink. 

“When he finally accepted [the fact] he had to own a car in Nashville, he didn’t buy some boring old Ford Escort,” Conner said. “He bought a car that runs on alternative fuel. To me, it showed that Freddie’s unlikely to sacrifice his values, no matter what he’s doing.”

Who is Freddie O’Connell?

When he announced his intent to run for mayor in April 2022, most political insiders agreed O’Connell was likable and knowledgeable. But they doubted his campaign skills, like whether he could raise enough money and boost his profile enough to overcome single-digit poll numbers. 

What most failed to realize was that O’Connell — a Nashville native, raised in the Richland neighborhood by mom Beatie, who taught at Montgomery Bell Academy, and dad Tim, a government official and musician — had become a fixture in the city’s political scene.

O’Connell also brought a solid understanding of communications and the city’s media landscape, built up from his days on radio and in the technology business. 

Despite representing just a sliver of Nashville in his District 19 council seat, O’Connell had an uncanny ability to be a local reporter’s best quote. Newsrooms would joke he was always available to comment on everything from a simple story about the latest council drama to an investigation into Airbnb’s influence.

O’Connell’s media and technology background dates back decades. At Montgomery Bell, he worked on the first yearbook staff to use a computer for publishing. 

Then, at Brown University — where O’Connell met Boon, with whom he shares two daughters — he worked at the school’s radio station and student paper, majoring in computer science. 

Boon returned to Nashville with O’Connell after college, eventually getting her medical degree from Meharry Medical College. 

She is arguably the most influential person in O’Connell’s life, serving as a behind-the-scenes advisor and coordinator on each of his political campaigns. 

O’Connell described her as the steadying hand critical to his success.

“She is incredibly organized, disciplined and hard-working,” O’Connell said. “I tend to be perfectly comfortable in chaos.”

Part of the reason O’Connell returned to Nashville was to start a career in Nashville’s burgeoning technology startup scene first at Conner’s Telalink. 

“It seemed normal at the time, but in hindsight it was crazy, we just had people showing up because they loved technology and wanted to be around it,” said Tim Moses, another co-founder of Telalink.

“Freddie had such an engineer mindset that you can fix everything and we shouldn’t leave things running inefficiently if there are better ways do it.”

O’Connell didn’t stay at Telalink long, moving around different startups over the years, including a stint as the head of technology at the Nashville Post. But before leaving, he met a key acquaintance: Mary Mancini. She would go on to head the Tennessee Democratic Party and play a significant role in his political career. 

For most of the mid-2000s, Mancini and O’Connell hosted Liberadio, a political show on Vanderbilt University WRVU.

“It raised our profile in the community because we interacted with so many guests in the political, activist and advocacy world,” she said. “It was a good way to get involved in the world of local, state and federal politics.” 

O’Connell shifted toward more community organizations during his years as a radio personality. He moved to Salemtown, where he now lives, joining the neighborhood association and eventually becoming its president.

He then joined Walk Bike Nashville, a fledgling nonprofit dedicated to making the city more friendly to those interested in commuting in ways without a car.

“We were completely ineffective for a long time,” David Kleinfelter, a founder of Walk Bike Nashville, said.

But with Walk Bike — which he also led as president for a period — and eventually his position with the Metro Transit Authority, O’Connell started laying the foundation of a political network, finding he wasn’t the only one fed up with the city’s lack of public transit and limited sidewalks. 

“He has the ability to find things he’s interested in, stay involved and, along with other people, help move things forward,” Kleinfelter said.

Through each step in his organizing career, O’Connell would seemingly hit a wall in what he could accomplish. With Walk Bike, he learned only so much could be achieved from outside government. On the transit authority, there became limits because he didn’t have a say in funding policies. While on the Metro Council, he learned the limited power he held in advancing a large-scale transit project.

Metro Council member Bob Mendes said it’s “difficult” as a council member to accomplish much without the mayor taking the initiative.

“A collaborative team approach will be more successful for the city and able to get more big projects done simultaneously,” Mendes said. “From what I’ve seen about Freddie’s leadership style, working with him as a colleague, I think that that’s something that he excels in.”

But that wasn’t always the case. Before O’Connell’s radio and community organizing days, he made another longshot political bid in 2002, this time for a state House seat held by future Speaker Beth Harwell.

As a 25-year-old, he ran as an independent candidate, believing neither political party fit him at the time.