Editor’s note: This story was based on conversations with more than 30 sources, including candidates, campaign staff, Cooper administration officials and Metro observers. 

Freddie O’Connell stepped to the podium before a raucous crowd at the Hutton Hotel that felt more like a concert scene than the victory party of a bespectacled transit nerd.

“This race was about all of us declaring what we want, say it with me: more ’Ville, less Vegas,” he said. The crowd erupted in the chant.

O’Connell had tapped into a sentiment lingering in the city for a couple of years now, that a place that once puffed out its chest as “It City” had gone too far in becoming a playground for outsiders instead of focusing on the livability of its residents. O’Connell finished in first place with 27 percent of the vote.

Across town at Coco’s, Alice Rolli’s supporters were no less engaged with her critique of Nashville’s future. 

“Do we want more of the same?” she asked. “Do we believe that letting the city council run the city is a good idea?”

“NO!” the crowd replied.

The former GOP operative and Haslam administration official had followed the 2015 playbook of her treasurer David Fox to a T, rallying Republicans to finish second with 20 percent of the vote and qualify for the runoff.

When Nashville returns to the ballot box in September, they will choose between the most progressive and most conservative candidates in the field, a fitting race in a nation that finds its politics similarly polarized. 

The race ultimately looks nothing like the one O’Connell entered 15 months ago. Back then, he believed it would be a referendum on Mayor John Cooper. But Cooper’s departure set off a chain of events that led to a wild scramble for money, staff and ultimately votes. Here’s how it all happened.

Mayor John Cooper announces he will not run for re-election. Credit: Tennessee Lookout/Special to the Banner

A little after 9 a.m. on Jan. 31, a notice went out to reporters for a 10 a.m. press conference in the media room at the Historic Metro Courthouse. Short-notice announcements were common during the pandemic, but not so much in 2023 — and this was different. A reporter texted T.J. Ducklo, Cooper’s press secretary, to ask if they needed to be there. “Yeah,” he responded, but wouldn’t confirm what it was about.

By the time Cooper reached the podium, the news had leaked that he would not be seeking a second term. For months, there had been no indication that this was a possibility. In January, Cooper’s team started preparing for a launch announcement and began lining up endorsements. From out of nowhere on Jan. 23, the police and fire unions announced they were backing Cooper. Scripts were written for ads and campaign hires were being made. Cyrus Shick, who wound up running Heidi Campbell’s campaign, had already been contracted for field work. Ron Owens, Michigan Gov. Gretchen Whitmer’s former political director, was being courted as campaign manager.

But first Cooper’s team needed him to shoot a video and pick an announcement day. A few days before he bowed out, one staffer said, Cooper couldn’t be pinned down on a date, and the people around him started to entertain the possibility the mayor would not run. 

At the press conference, Cooper took a victory lap for fixing some of the city’s financial issues, but also hinted that he was a little bruised from three tough years. 

“In many respects, 2020 was itself a full term in office,” Cooper said, echoing the sentiment of big city mayors across the U.S. who had been on the front lines of the COVID pandemic. It was a bruising time as local officials balanced public health and economic livelihood with terrible consequences everywhere. 

Cooper’s personal favorability numbers were in the low 50s, which is decent, but not high for the mayor of a boomtown that seemingly had escaped the pandemic without lasting economic damage. Plaguing him was a problem somewhat outside his control: A majority of Nashvillians thought the city was on the wrong track. For some voters, it was the issue of affordability, for others a fear of violent crime. At some point, the mood of an electorate can turn on an incumbent when right-track/wrong-track numbers are upside-down. Just ask his predecessor, David Briley.

O’Connell, former MDHA exec Matt Wiltshire and At-Large councilmember Sharon Hurt had already entered the race. It was rare for an incumbent Nashville mayor to face three strong candidates. Outside the press conference, a trio of Cooper’s staff — Ducklo, Ben Eagles and Sam Wilcox — were defiant that Cooper would have won reelection. But that referendum on John Cooper’s administration, his accomplishments and his 34 percent property tax increase never happened.

Across town, Marjorie Pomeroy-Wallace was watching all of this unfold on her phone. 

O’Connell’s campaign manager had a rough few days, with her campaign finance person giving birth three days before disclosures were due. Pomeroy-Wallace had to hand-enter 7,000 entries before the disclosure could be filed with the Davidson County Election Commission. On top of it all, she had a medical appointment she couldn’t miss.

While Pomeroy-Wallace was sitting in the doctor’s office, O’Connell called to ask if she had heard about the press conference and the rumors that Cooper was out. Pomeroy-Wallace said no and flipped on a stream of the press conference. As she watched the past eight months of work unravel before her eyes — the budget, planning, fundraising and messaging would all be different without an incumbent opponent — her doctor took her blood pressure. It was through the roof.

They started at square one and devised a new plan. Without Cooper to run against, O’Connell needed to own the progressives and build grassroots support around people who liked his encyclopedic knowledge of all things Metro. 

Wiltshire, meanwhile, was piling up cash. Between a $350,000 loan and some aggressive fundraising in the business community, he had amassed a $1 million war chest by the time of the Jan. 31 disclosure. Like O’Connell, his reason for entering had been predicated on unhappiness with Cooper. Unlike O’Connell, his support came from a broad swath in the middle, including business leaders who found Cooper prickly to deal with and slow to move. 

Without Cooper as a foil, it was more important than ever to increase Wiltshire’s name ID with voters. O’Connell had been using his platform on the Metro Council for months with great success opposing the plan to build a new stadium for the Titans. Without a natural way to make news, Wiltshire needed to get on television, and his team reserved time around the Feb. 12 Super Bowl to roll out his first ad. 

Where did all of this leave Hurt? Although she joined the race in December, she didn’t really start building a campaign until late January, six months after O’Connell and Wiltshire. Elected twice countywide to the Metro Council, Hurt was banking on strong ties to Bellevue and North Nashville to give her a base of both support and fundraising. Now just days after hiring a campaign manager for one race, they needed to formulate a completely different strategy.

A week after Cooper’s exit, retired AllianceBernstein COO Jim Gingrich entered the race. He spent much of 2022 conducting a listening tour of business and civic leaders (and even a few journalists) trying to decide whether to run against Cooper. He conducted his own poll. His entry sparked a combination of bemusement and derision that someone who moved to Nashville just five years before could now run the city. But where some saw hubris, Gingrich supporters saw an experienced executive who was a breath of fresh air. Over the next two months, he raised money at a rate higher than anyone except Wiltshire, despite the fact that some of his personal network in the financial services industry was limited in what they could give him because of Securities and Exchange Commission rules. 

Soon, a number of people were exploring the race: Bob Freeman, state legislator and son of 2015 candidate Bill Freeman; Councilmember At-Large Bob Mendes; Stand Up Nashville founder Odessa Kelly, who ran for the 7th Congressional District seat the year before against Mark Green; and Tara Scarlett, president of the Scarlett Family Foundation and daughter of retired Tractor Supply executive Joe Scarlett. All of them looked at the race and passed.

But four more serious candidates entered: state Sen. Jeff Yarbro, Alice Rolli, state Sen. Heidi Campbell and Vivian Wilhoite.

Yarbro was first, quitting his law firm job at Bass, Berry and Sims and announcing on Feb. 17. Then came Rolli, a former Haslam administration official, on March 3. A month later, Campbell got in, announcing her bid on the steps of the courthouse beside Freeman and fellow Davidson County delegation members Rep. Bo Mitchell and Rep. John Ray Clemmons. The last to enter was Assessor of Property Wilhoite.

Why did they all get in? By entering the race so late — Wilhoite didn’t even formally announce until May 1, less than three weeks before the deadline — there now was a mad scramble for voters and cash. None of them could self-fund the same as Gingrich, who pledged $2 million to his campaign right out of the gate.

Yarbro had stepped down from his minority leadership position in the Senate in December and relished the opportunity to do something other than be part of a superminority that constantly lost on core Democratic issues like gun control and abortion rights. Rolli saw the same lane to a runoff her campaign treasurer David Fox had in 2015 — a Republican in a field of Democrats — and thought Cooper’s property tax increase and a perception of rising crime gave her an opening. 

Campbell was another matter. A former mayor of Oak Hill, she was fresh off a loss to Andy Ogles in the 5th Congressional District race a few months before. It gave her a tremendous advantage in name ID, something borne out in an early poll that had her with 20 percent of the vote. She said in her announcement that she looked at the field — which included her Senate colleague Yarbro — and didn’t see the next mayor. The two of them butted heads in a December meeting of the Senate Democratic Caucus that elected Raumesh Akbari of Memphis as the new minority leader and London Lamar as the new caucus chair. Multiple people recounted Campbell as still being furious over the outcome of the caucus and saying that Campbell told them, “I can’t just let Jeff win.”

Wilhoite filed a treasurer form with the election commission in early April, but waited a month to formalize her entry. What she and Campbell both found by waiting so late was that much of the available staff and campaign leadership in the city had been snapped up already. Campbell hired Shick to run her campaign, while Wilhoite hired Kevin Teets, a veteran of the Freeman campaign in 2015. A two-term councilmember from the Antioch area, Wilhoite was no stranger to outworking her opponents. Hurt, realizing that having two high-profile Black candidates on the ballot might split the vote, reached out to Wilhoite several times to ask her not to enter, but staffers say Wilhoite never called her.

Alice Rolli speaks to supporters on Thursday night, Aug. 3 at Coco’s Event Center. Credit: Eric England/Nashville Scene/Special to the Banner

May and June saw the mayoral candidates settle into a rhythm. By day, almost all of them were doing some kind of call time, talking with political influencers and donors trying to raise support and dollars. By morning and by night, most of the eight main candidates participated in an endless string of mayoral forums.

The forums are an odd byproduct of Nashville’s political culture and a hollowed-out media that doesn’t have the capacity to cover these races as they did in previous decades. Day-to-day coverage, particularly on TV, was sparse and hard to find outside of sponsored “debates,” as most broadcast outlets feared not giving candidates equal time.

By late spring, every civic organization or interest group with more than 20 supporters seemed to be hosting a forum. In many cases, they were black holes of information, with no media partner to share them and no one at the organization recording and posting it on the internet. Candidates were spending two or three hours — plus preparation time — for each event to convince a handful of voters.

At one point, several of the campaign managers got together to try and impose standards on the events: Each one needed a media partner to publish either the entire event or coverage of it; the events needed to be open to the public; the forum should be well-publicized. The cartel even attempted to recruit former Mayor Bill Purcell as a kind of forum czar, but he declined. But the effort fell apart when Gingrich’s campaign hesitated — the first-time candidate felt uncomfortable telling minority organizations what to do. A few weeks later, he regretted the decision as new forums kept being added.

Experienced campaign managers will say it takes 60 to 90 days to organize and build out a campaign apparatus. O’Connell and Wiltshire’s six-month head start allowed them to actively recruit support during this time. By late February, O’Connell’s team had begun knocking on doors regularly while Wiltshire raised record money to prepare for a summer of ads and a big push in the field.

It was a fast-moving process for Gingrich, who opened his checkbook wide. By April, the campaign had already shot a series of ads and began saturating broadcast TV with them. Campaign manager Emily Cupples, a former state Democratic party staffer, built a comparatively large field operation to complement the air war they began waging. The campaign introduced Gingrich to the city with a series of fast-moving spots that emphasized voters’ frustrations with a changing Nashville. “I’m fed up, but my friends call me Jim,” he said in one.

For others, though, building a strategy meant choosing what not to do. Campaigns think of direct voter contact in terms of four general buckets: field work, direct mail, TV and digital. All of them have drawbacks. Field operations are vital for reaching voters face to face, but can be expensive without a big volunteer base to help or a long lead time. Direct mail is a crapshoot because it’s guaranteed to reach a voter, but it has high odds of being thrown in the trash. Traditional broadcast ads are expensive to produce and get to air, but they pick up a lot of older voters who still watch local programming. Digital has many dimensions, from email to social media to web-based ads, and is one of the most cost-effective, though there are demographic risks because a lot of older voters are not big digital consumers.

Hurt raised $114,000 in the first quarter and was ahead of only minor candidates Natisha Brooks, Fran Bush, Stephanie Johnson and Bernie Cox in cash on hand, putting an immediate damper on her possibilities. Her strategy had to be based on shoe leather and personality.

The two state senators represented completely different approaches to the race. With higher recognition than anyone else in the field, Campbell and Yarbro had a built-in advantage. A poll for a charter advocacy group introduced the first jolt to the campaign. It showed Campbell leading the race with almost 22 percent of the vote and Yarbro close behind with 17 percent. Early polls generally are tests of name ID, and Campbell’s recent congressional run let her outpace the field easily. Fundraising, though, was going to be a challenge, and neither could afford the full campaigns that Gingrich and Wiltshire were running.

Yarbro moved $141,000 over from his state Senate account and loaned himself another $50,000. He was banking that he could ride his high favorables until July so he could raise money, build a lean organization and then unleash an ad blitz that would push him over the top. Campbell’s team chose a ground path and hired a big staff to run a field operation that let them build on Davidson County residents who had voted for her twice in the past three years. She wouldn’t have the money to stay on air, but if she turned out her people to the polls, the TV wouldn’t matter. 

Gingrich’s team was riding high on the strength of an internal poll in May that showed the retired executive slowly rising. The ads that saturated every local newscast and streaming device were starting to make a difference. It was proof of concept: If Gingrich could continue a slow, steady rise, he would be well positioned by August to have a shot at the runoff. In addition to the commercials, Gingrich had added a large staff of field personnel that knocked on thousands of doors and got positive feedback from both Republicans and Democrats.

An early July poll, though, knocked Gingrich back to earth and upended the entire race.

District 35 CM Dave Rosenberg was impatient. One of O’Connell’s main backers on the Metro Council, his day job is running the political consulting firm Harpeth Strategies. He decided to run a poll July 5-6 himself to see if all of O’Connell’s field work was paying off. The survey itself was not perfect. Parts of it matched the demographic profile of Davidson County, but not perfectly. It went heavy on college-educated voters. But parts of it did match up enough to be useful enough to show direction. And what it showed was that O’Connell had slingshot into the lead:

  • O’Connell: 20 percent
  • Wiltshire: 15
  • Rolli: 13
  • Campbell: 7
  • Yarbro: 6
  • Gingrich: 4
  • Hurt: 3
  • Wilhoite: 3

As the poll began getting passed around the campaigns, NewsChannel 5 got a copy and ran a story about it. In some campaigns, the poll smelled like a plant. Yarbro’s campaign staff was sure O’Connell was trying to cement a narrative right as their first ad, a piece on gun safety, had begun running. O’Connell, meanwhile, had hit the airwaves with a spot pitting him against “billionaires and bachelorettes.”

Gingrich, who had been hoping for a continued rise, had to know if the numbers were true. His pollster came back 10 days after the Music City Research poll landed with substantially the same results: O’Connell was in first with 18 percent and he was sitting at 5 percent. His early rise had stalled with $2 million sunk into the effort. Early voting began three days before on July 14. Should he stay in? Should he get out? He pulled the plug, angering some voters who had already cast their ballots. Ultimately, he reasoned, it was more honest for him to get out than to stop spending money and coast into Aug. 3.

The Rosenberg poll kicked off a furious round of surveys with five different polls coming back in eight days between July 13 and 21. Whatever the deficiencies the Music City Research poll might have had, it had uncovered the same trend everyone else did: O’Connell was leading the pack, Wiltshire and Rolli were duking it out for the second spot, Yarbro was alive, Campbell was stuck in single digits and Hurt and Wilhoite were afterthoughts. 

Music City Research7/13 Poll7/17 Poll7/20 Poll7/20 Poll7/21 Poll7/25 Poll
Freddie O’Connell20141821162119
Matt Wiltshire15141412141015
Alice Rolli1381413131314
Heidi Campbell7898789
Jeff Yarbro68111091213
Jim Gingrich48535
Sharon Hurt346564
Vivian Wilhoite337544

Attendees at Jeff Yarbro’s party at Elliston Place Soda Shop look at early returns showing Yarbro in 4th place on Thursday, Aug 3. 2023. Credit: Nashville Scene/Hamilton Matthew Masters/Special to the Banner

Yarbro’s closing ad, titled “Naysayers,” is the last image many Nashville voters had of the senator before entering a voting booth. In some ways, it was the ideal version of him: A propulsive beat and inspiring words were wrapped around images of a man of action. Television commercials, when they work, are about leaving a positive impression. But local races are rarely about just TV and are mostly won on the ground, door to door, one voter at a time.

In the last week of July, as temperatures climbed into the mid-90s and the heat index reached triple digits, campaigns hit the sidewalks armed with data as they homed in on their voters. Campaigns sift through reams of available public information and combine it with proprietary data — usually compiled by the two main political parties — and overlay their own voter contact to develop an available universe of voters. Then, volunteers and paid staff walk the streets, knocking doors and leaving campaign material for targeted prospective voters. 

Makayla McCree, 25, was the face of the Yarbro campaign in Charlotte Park the weekend before the election. Parking at Charlotte Park Elementary, she worked her way through this changing neighborhood, past tall-and-skinny new construction elbowed in between 1950s and ’60s ranch homes. In an hour, she’ll get to 13 houses, starting each conversation the same way. “We know that you’re a faithful voter.”

Sometimes the data is spot on: There’s a union sticker on one truck as she walks up the driveway. Other times, McCree sees an opposing yard sign and knows she’s fighting an uphill battle, like the Rolli supporter she encountered just two houses later. More than half of her targets were not home. In all, she counted a couple of possibilities and one firm yes — at her last stop.

“I needed a win before I stopped,” she said, sweat pouring off of her forehead.

The problem for Yarbro, though, is that by the time McCree and her compatriots are finished, they will have knocked on only 5,000 doors. The campaign simply didn’t have the capacity to reach more homes, which is why Yarbro made a pitch to Gingrich for his field staff the day after he dropped out. They ended up going to O’Connell.

A little south in Belle Meade, Clifton Wright is working his way up Greeley Drive on behalf of Alice Rolli. A retired veteran, he’s on friendly turf here as he knocks on one door.

“She’s the low-tax lady, right?” said a homeowner. “She’s the police, fire department, EMT retention,” Wright responds. “Also the infrastructure of the city.”

Rolli’s messaging has been deliberate. Although she was against Cooper’s tax increase, she’s got no plans to roll it back, a move that would keep her from hiring more cops. Her campaign has been operating alongside a friendly PAC called Save Nashville — launched by members of the nearby Belle Meade Country Club — that has been hammering Fox News-style images at voters to drive up Republican turnout. 

Wright got to 15 houses in an hour, but with only three people answering their doors. Two answered and seemed open to Rolli, but weren’t definitive. That’s the way canvassing goes sometimes. One said he had already voted early, but didn’t tell who he was supporting. In 2015, David Fox followed the same playbook into a runoff, knocking on a ton of doors and letting an outside group spend on his behalf. Rolli’s campaign had knocked on 27,521 doors, the second-most of any candidate, trying to find their voters by Election Day.

Meanwhile, Sydney Carroll was making her way through Sylvan Park for Heidi Campbell. Armed with extra water bottles for the heat and the Barbie soundtrack on her car stereo for motivation, she was one of a number of young volunteers for Campbell. 

There’s a feeling of community for Carroll in working for Campbell again. Young, progressive and politically active, Carroll and her volunteers have a group chat where they send funny quotes from texts or phone calls with voters. Most of them joined Students for Campbell in the fall, and Caroll said they’re “living in Heidi-land everyday.”

Campbell wants to build “a Nashville to live in, not visit,” Carroll told voters. It’s been a theme throughout her campaign (and, well, many candidates’ campaigns to be fair) and one that they had to emphasize on a retail basis because Campbell never had the funds to make a sustained run on TV. Her staff forecasted this to donors and media in June, saying that they would emphasize a ground strategy and attempt to overperform in her 20th Senate District, which wraps around the outside of the county. It explains why Campbell’s staff costs relative to her fundraising were so high — 41 percent — when she made her first finance disclosure. Most campaigns like to keep that number under 30 percent to free up more money for other direct voter contact. 

Her strategy had a drawback, though. The lack of TV functionally meant a lack of marketing to donors late in the campaign. In the first three weeks of July, Campbell brought in  just $38,746, less than a third of what Wiltshire and O’Connell raised and fifth among the major candidates. With no money of her own to add, she entered the final weeks with only $40,000 in cash on hand.

In the southeast part of the county, the brother/sister duo of Raymond and Rhea Kinnard worked their way through Antioch for Matt Wiltshire. Rhea said she doesn’t know a mayor that won without winning the area, a high-growth mixture of immigrants, African Americans and blue-collar residents. Many have flocked toward the southeast in search of affordable housing, the one thing both Kinnards emphasize when talking to voters. Wiltshire has made most of his closing message about housing, emphasizing his time at MDHA as giving him the skills to bring more affordable units to the county.

“If we’re not canvassing, we’re making calls, just whatever we have to do and need to do,” Rhea said. The campaign reached 15,000 doors and made another 150,000 calls on behalf of Wiltshire. Combined with the TV blitz, he raised more money and spent more than anyone but Gingrich. Some of the Kinnards’ pitch — heavy on experience, lighter on policy — was made not just to people with a documented voting history, but to those who hadn’t voted before. 

Wiltshire tried to find a middle path and actively sought both Democratic and Republican voters. It drew the wrath of progressives online, particularly when he was endorsed by the Fraternal Order of Police. But polling showed he was finding support with the African American community and some traditional Republicans, with most of the MAGA crowd either voting for Rolli or staying home. 

Being in the middle made him a target the week of the election, as text campaigns from a group called Americans for Hope and Prosperity hit him from both the right and the left. A set of runoff scenarios run by political operative Ward Baker might have revealed the texts’ motive, if not their identity.

“We tested four separate runoff scenarios.

• O’Connell 49% – Rolli 23% – Undecided 28%

• O’Connell 33% – Wiltshire 37% – Undecided 30%

• O’Connell 36% – Yarbro 37% – Undecided 26%

• Wiltshire 33% – Yarbro 38% – Undecided 29%”

O’Connell would benefit from Rolli making the second stage. Yarbro, who trailed Wiltshire in most polls, would have liked his chances against O’Connell if he could just leapfrog into second. But that could also be overthinking the situation, one campaign staffer observed, as Rolli needed to pick up every available Republican in order to make the runoff herself. There are lots of suspects for who sent the texts, but almost no way of finding out.

Canvassing in the middle of the Napier Homes for O’Connell, Nicole Valentine wasn’t concerned with the 3D chess of attack ads. She’s an elementary school teacher who lives in the neighborhood, and she saw one of her students with their friends during the canvas. Scott Dietz, O’Connell’s field director, said they try to send canvassers to their own neighborhoods whenever they can, because it’s a lot more effective to say, “Hey, I live one street over and here’s why I like Freddie.”

One of those neighbors is known simply as “Miss Gloria” to Valentine. An elderly African American woman who’s lived in Nashville her entire life, she represents the exact voter O’Connell — the darling of young white progressives — has had some trouble reaching. Miss Gloria talks about seeing the city change and how she feels people like herself are being left behind and forced out. Valentine talked with her and left behind a card, pointing out one line from O’Connell in particular in large type: “I want you to stay.”

That line was the byproduct of an impromptu speech O’Connell gave at a meet-and-greet early in the campaign. The slogan has resonance in a city whose residents, polls say, are weary of the pace of change and soaring cost of living. In all, O’Connell’s campaign clocked 30,000 doors since February on the strength of more than 250 volunteers, the most of any candidate. 

Freddie O’Connell speaks to supporters at Analog at the Hutton Hotel on Thursday night, Aug. 3. Credit: Angelina Castillo/Nashville Scene/Special to the Banner

In the end, 2023’s mayoral election played out almost exactly the same way as 2015. The most progressive candidate got in the race first — Megan Barry instead of O’Connell — raised money slowly and steadily, built a volunteer army and knocked on the most doors. The most conservative candidate — Fox instead of Rolli — found enough voters on the right disenchanted with the city’s political establishment, got the help of an independent expenditure and knocked on the second-most number of doors to stake out a place in the runoff. 

Meanwhile, the well-funded political center ate itself again as Wiltshire and Yarbro robbed the votes from each other necessary to make the second round. In 2015, Bill Freeman and Charles Robert Bone did much of the same, spending millions to finish third and fifth.

For months, the O’Connell and Rolli camps have been quietly hoping for this matchup, with both viewing a race against the other as their best chance for winning.

“Our city is too great to allow it to follow the recipe book that has failed too many other big cities, of higher taxes, higher crime and failing schools,” Rolli told her supporters Thursday night.

“Nashville’s next steps are born out of hope, not fear,” O’Connell told his.

In six weeks, the city will choose one of their visions for the future.

Additional reporting by Connor Daryani, Addison Wright and Braden Simmons.

Steve is a three-decade veteran of newspapers, working around the country at places like the Washington Post and Chicago Tribune before returning home to Nashville in 2011 to edit The City Paper and Nashville...