A bloody clipboard and biodiesel car: The story behind Freddie O'Connell's rise to Nashville mayor

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

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

A bloody clipboard and biodiesel car: The story behind Freddie O'Connell's rise to Nashville mayor – Tennessee Lookout

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.

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.

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.”

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.

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.

– Tim Moses, founder, Telalink and former colleague

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.

Metro Councilmember Freddie O'Connell walks down Second Avenue in Nashville, site of a Christmas Day 2020 bombing. (Photo: John Partipilo)

Nashville Mayor-elect Freddie O'Connell embraces former mayoral rivals Vivian Wilhoite, Davidson County property assessor, and businessman Jim Gingrich. Both endorsed O'Connell in the runoff. (Photo: John Partipilo)

Freddie O'Connell during a May 2023 mayoral forum.(Photo: John Partipilo)

O'Connell hugs Councilmember Terry Vo, while former council member Bob Mendes looks on. (Photo: John Partipilo)

On Election Night, Aug. 14, 2023m supporters swarm Mayor-elect Freddie O'Connell for selfies. (Photo: John Partipilo)

Matt Pulle, a former reporter at the Nashville Scene who covered the race and is now an O’Connell supporter, said he obviously stood little chance.

“You know, as a local reporter, during an election, you just interview a lot of people running for office, or who are in office, who are just not smart,” Pulle said. “I remember him as a very thoughtful guy who took kind of an issue-by-issue approach to politics. He didn’t have this ideology that dictated his views.”

In hindsight, there were a few problems with the 2002 O’Connell campaign.

First, on the advice of campaign manager Alan Coverstone, he chose to run as Thomas F. O’Connell, his birth name, to present himself as a more serious candidate.

“I screwed up when I didn’t see the value of the slogan ‘Ready for Freddie,'” Coverstone said.

Additionally, the campaign was on a shoestring budget and had no volunteers, basically run by Coverstone and Boon.

“At the time, he was much more interested in doing it himself,” Coverstone said. “He felt like if he wasn’t knocking on the doors, he was losing out on something.”

O’Connell lost, finishing a distant third to Harwell, but it provided him with lessons on the value of volunteers and the importance of campaign messaging, both defining features of O’Connell’s mayoral campaign success.

I remember him as a very thoughtful guy who took kind of an issue-by-issue approach to politics. He didn't have this ideology that dictated his views.

– Matt Pulle, attorney and former Nashville Scene reporter

The slogans “Ready for Freddie”, “More ‘Ville, Less Vegas,” and “I want you to stay” became minor sensations, allowing O’Connell’s advertisements to distinguish themselves from a crowded field.

Metro Council member Sean Parker said “I want you to stay” came out of a late-night dinner the two had at the M.L. Rose in Capital View after a Metro Council meeting.

Parker had just attended Matt Walsh’s anti-trans rally at the Capitol, where several of the speakers who had just moved to Tennessee were telling people to move if they didn’t like the state’s conservative policies.

“As someone who grew up here, having a recent California transplant shout something like that at me kind of stuck in my craw,” Parker said. “At one point, standing outside the restaurant — which had closed at that point — I came up with ‘I want you to stay.’

“It was a light bulb-type moment. We liked it not so much as a campaign slogan to earn votes but more a message that Nashvillians needed to hear.”

O’Connell would lead his victory speech with the slogan.

It would take 13 years, but O’Connell eventually returned to electoral politics in 2015, contesting an open Metro Council district spanning downtown, Germantown, the Gulch, Salemtown and Napier.

He faced a large field in a low-turnout race due to the nature of the position, where a disciplined voter reach-out strategy is necessary.

Joe Sheeran, who worked on both of O’Connell’s Metro Council races, said each night he would sit down with O’Connell to recap the day, describing what they learned about the community and swapping stories of their door-knocking.

“I remember a dog lunged at him, and he had to fend it off with his clipboard. He came back with it all bloodied,” Sheeran said. (To note, O’Connell said the dog was biting the clipboard hard enough that its gums bled. Gums aside, both parties walked away unscathed.)

“But the thing that sticks out to me the most is his ability to remember people and remember details.”

Ultimately, the 2015 race wasn’t particularly close, with O’Connell snagging 54% of the vote on election day and avoiding a runoff.

While serving on the council, O’Connell slowly built up a reputation for getting into the weeds on issues and knowing precisely who to talk with.

“It’s often said Nashville runs on relationships,” Parker said. “You can go up to Freddie and ask him about an issue, and he’ll start rattling off people in government or in the nonprofit world who can help.”

O’Connell ran unopposed in 2019, winning his final of the two terms allowed for a council member.

Over the next four years, in the shadow of John Cooper’s only term as mayor, O’Connell said he felt the need to run.

He would work with the administration on issues like regulating transpotainment vehicles, transit funds and more money for the homeless impact division.

But he also criticized the administration, like when he offered to take people’s recycling to centers personally, rebuking city officials for allowing the suspension of the pickup service just a few years after they raised property taxes.

You can go up to Freddie and ask him about an issue, and he'll start rattling off people in government or in the nonprofit world who can help.

And then there was the Titans stadium.

O’Connell said the final push for him to run was when Cooper didn’t discuss the new stadium in his 2022 State of Metro speech.

“I thought, wait a minute. We’re not talking about the single biggest thing we are going to put in front of voters and the council,” O’Connell said. “I felt where we had been over the past five years was an era of restoring trust in local government, and that was contributing to a breach of trust.”

Cooper’s decision to push the Titans stadium while bowing out of the race at the last minute are two inflection points that would define the 2023 Nashville mayoral campaign.

As an incumbent mayor, all signs pointed to Cooper running for reelection.

For a while, it seemed like the race would be between Cooper, O’Connell, former Metro official Matt Wiltshire and council member Sharon Hurt.

But Cooper’s change of heart threw a wrench in the race, initially hurting Wiltshire because it led Rolli, a former Republican strategist, Sens. Jeff Yarbo and Heidi Campbell, and businessman Jim Gingrich to enter the race.

Between Campbell, O’Connell, Wiltshire and Yarbro, the race effectively became a Democratic primary, with Rolli on the other side if she could consolidate the Republican vote.

Very few things distinguished the four candidates, except for their views on taxpayer dollars funding $1.26 billion of the $2.2 billion Titans stadium. Yarbro and Campbell both voted for it in the state Senate, and Wiltshire backed the deal.

O’Connell said he was always skeptical of the deal, voicing those concerns early in the process, but his mind was made up after a set of community meetings held by Mendes.

On April 26 — three months before the election — O’Connell voted against the stadium deal, turning it into a campaign advertisement and eventually rocketing him from a district councilmember to the most prized political office among Democrats in Middle Tennessee.

The spotlights and the pressures will be like nothing he’s ever faced.

O’Connell will have to navigate the landmines thrown by Republican leaders, who at any moment could decide to preempt any of the policies he introduces.

At the same time, the city has been besieged by a string of one-term or less mayors who have yet to be able to turn the tide of angst among Nashvillians about rapidly increasing housing prices and concerns over a growing focus on tourism over city services, like police and transit.

And from day one, he’ll likely be labeled the “progressive mayor of Nashville.”

“Does it scare me?” O’Connell asked. Without pausing, he gave a simple answer:

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by Adam Friedman, Tennessee Lookout September 18, 2023