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Commentary
(Editor’s note: An earlier version of this story attributed a quote in the last paragraph to Alice Rolli instead of Freddie.)
There are two ways to foreshadow how things will go down Thursday night when Nashville’s aeonic mayoral election saga finally streams its series finale. Most likely is the conventional wisdom prediction (it’s not called conventional for nothing): progressive, experienced politico running a generally safe, amply funded, mistake-free campaign takes down conservative Republican political amateur, and with plenty of room to spare.
Less conventionally wise is the big honkin’ upset: the conservative persuades a very large number of Davidson County Trump voters who had zero interest in her campaign in the general election five weeks ago to gin up enough interest in her now to show up for a runoff.
If advertising dollars win elections then Freddie O’Connell beats Alice Rolli handily. After the August 3 general election narrowed the field to two, O’Connell went back on TV —broadcast and cable — as well as digital within a couple of weeks and has stayed there with a steady ad spend that will end up totaling right around $300K for the runoff.
Rolli, meanwhile, stayed off digital until late August, and off the airwaves until after Labor Day, when she launched a broadcast ad buy for the final week (including a small bit of radio) that totals around $90K. She has had air cover for weeks from Hedge Fund Guy PAC — the Save Nashville PAC, fronted by Tom Landstreet, a protegee of supply side economist Arthur Laffer — which has spent $88K airing spots that vilify O’Connell as an ominous menace looming over our fair city (or perhaps San Francisco) and anoint Rolli as its savior. The PAC is also throwing $15K into a final-week radio blitz on several local stations, and while radio may not be dead, it isn’t very expensive: $15K over less than a week buys you a heck of a lot of spots.

But ad spending by itself doesn’t win elections. If it did then neither O’Connell nor Rolli would have made the runoff. And while O’Connell has both outraised and outspent Rolli during the runoff period by large margins, when you factor in PAC support her spending deficit compared to O’Connell on paid media, while substantial, isn’t vast. Her message is out there. And late additions to her and the PAC’s media buys in the closing days of the race signal something other than surrender.
All that said, a look at some pretty simple voter math paints a vivid picture of the steep electoral hill Rolli has to climb to pull this out. Let’s make some assumptions about who will vote and model the runoff outcome accordingly. To keep eye-glazing in check I’ll use round numbers here (but my calculations of predicted outcomes are more precise).
Let’s start with a thought experiment that assumes the runoff electorate is the same set of humans who voted August 3. This is not a crazy assumption since in the modern history of contested Nashville mayoral runoffs (2007, 2015, and 2019) the runoff turnout has deviated from the general turnout by more than 6% only once — in 2019 when it actually dropped by almost 11%. This year turnout for runoff early voting was up compared to August but generally in line with the past.
In the August general election O’Connell received 27,500 votes and Rolli 20,400. Let’s assume that every one of those voters turns out for the runoff and casts the same vote. Then take the 2,500 votes for the three candidates in the general who either have endorsed Rolli or lean conservative (Natisha Brooks, Fran Bush, and Stephanie Johnson) and give every one of those votes in the runoff to Rolli.
Now let’s consider the 50,400 votes that went to the other six in the first round (Matt Wiltshire, Sen. Jeff Yarbro, Sen. Heidi Campbell, Sharon Hurt, Vivian Wilhoite and Jim Gingrich), five of whom have explicitly endorsed O’Connell, and ask ourselves: what fraction of these ballot refugees looking for a new home can Rolli snag?
If O’Connell gets three of every four votes that went in the first round to those six — which many would call a lowball estimate — he wallops Rolli 65-35%. If O’Connell gets just half of those votes, which seems implausible, he still beats her by more than four percentage points. Rolli would have to win a majority of the refugees — 54.46% to be exact — to overtake O’Connell with the same voter pool. Steep indeed. More like perpendicular.
Of course, Rolli’s prospects don’t depend just on one fuzzy-headed pundit’s calculus rooted in a thought experiment about an identical voter pool (arithmetically impeccable though it may be). Her campaign finance disclosure for the runoff period revealed she raised more from donors since the general than she had raised in total up to that point, so she has perhaps found some new voters, or in any case some new checkbooks.
The question, then, is how many new GOP voters can Rolli bring to the runoff? The ignis fatuus, or idea, of a conservative takeover of city government has always rested in large part on the imagined activation of the multitudes of Davidson County GOP voters who turn out for fascism (just over 100,000 for Trump in 2020) but seem indifferent to participation in municipal democracy.
Rather than focus on Trump voters in a presidential election, a better way to ponder the universe of Davidson County Republicans who might turn out for Rolli is to look at Nashville turnout for recent contested GOP state races. In 2020, votes in the GOP primary for U.S. Senate (starring Bill Hagerty and Dr. Manny Sethi plus a large cast of extras) totaled a little over 34,000. The 2018 GOP primary for governor (Bill Lee, Diane Black, Randy Boyd, Beth Harwell et al.) saw a total of 43,000 votes cast in the county, a measurable slice of which might have been cross-over Dems trying to give local moderate Harwell a shot.
If we take those two turnout figures and make a Rolli-friendly assumption that there are around 40,000 Republican voters who might be open to her pitch, the challenge still remains more than daunting. In the version of my vote-reallocation math above where O’Connell gets 75% of the so-called refugee votes, Rolli loses by almost 30,000 votes. Yes 40,000 is more than 30,000, but presumably most of these 40,000 are already voting for her. And let’s keep in mind that 75% for O’Connell’s share of the refugees is a floor. Bottom line: Rolli needs tons of new voters in the runoff, and it’s not clear where she finds them.
The bigger question heading into the closing days of the race is why Rolli’s headwinds seem so much stiffer than David Fox’s were when he made the mayoral runoff as the conservative option eight years ago. Here are three quick theories.
Theory one: The county has grown more progressive and less conservative. Metro council elections in the last couple of cycles offer some loose evidence for this theory, and of course the era of Trump, during which so many Republicans have chosen to demonize cities as cradles of civilization collapse, throws turbulence in the flight path of any self-identified conservative seeking an urban leadership post. Sure, right-track-wrong-track polling has Nashville currently under water, and Rolli has tried gamely to position herself as a change candidate, but people live in cities because they like cities. A candidate identifying with and embraced by the party that hates cities has a natural disadvantage that has only grown larger in recent years.
Theory two: The current vortex of political tyranny that is the city’s “relationship” with the state’s GOP supermajority — an issue that polls show voters care about — puts any Republican contender in a difficult bind. Rolli has tried to soft sell this by framing herself as a moderate who speaks their language and can “reset” (her favorite verb) the relationship. Hell, maybe she can.
But the problem is that Rolli has been unwilling to call out the truly offensive parts of state GOP rule — the racism, the bigotry, the hostility to reproductive freedom, health care access, and voting rights — leaving her without grounds for affront when Nashvillians make inferences that as mayor she will accommodate (if not advance) the state Republican party’s agenda. But then again if you do call out the madness, where do you find those tens of thousands of votes you need from people who like the madness?

Theory three: Rolli is a flawed candidate who ran a defective campaign. The unfortunate missteps have been sufficiently documented: her awkward inability to fend off questions about Trumpiness, silly and unnecessary pledges about taxes and school takeovers, skipping too many mayoral forums, and of course ProudBoyGate, which forced a wholesale change in her campaign consultant team late in the game.
But it’s not just the mistakes. While she has improved as a communicator over the months she’s been in the race, Rolli remains a candidate with limited charisma who describes problems adequately but solutions ineffectively (or not at all), and her lack of depth as to how the city works is just as evident at the end of the race as it was at the beginning. Her schtick about being not part of the political crowd is listless and stale, and the attempt to convince voters that her opponent’s public service in city government should disqualify him is foolish.
Rolli does at times frame herself as politically experienced, reminding voters that she worked for the likes of GOP non-crazies Lamar Alexander, Bill Haslam, Randy Boyd, and (no longer non-crazy) Sen. Bill Hagerty. Pointing this out does make some wonder why it is that none of those four have publicly endorsed her candidacy, and only one has made a donation to her campaign — Alexander with a late contribution that showed up in last week’s disclosure. (I would have asked the campaign for a comment on this, but they stopped returning my emails a long time ago.)
So as election day approaches, is there more readiness for Freddieness than Rolli can overcome? Responding to last week’s campaign finance disclosures showing O’Connell outraising her for the runoff by a three-to-one margin, he told the Nashville Banner that “donor energy isn’t exactly the same as voter energy,” adding that “our overall operation is focused on getting voters back out to the polls.” That makes perfect sense for O’Connell, but for Rolli, as the voter math shows all too clearly, merely getting the same voters back out to the polls would risk situating her campaign on the business end of an avalanche. One presumes that both campaigns in the final days are vigorously reminding supporters that avalanche warnings don’t always pan out.
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Bruce Barry