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

Alice Rolli is caught between two worlds.

In the world she grew up in, Lamar Alexander was king. The former governor and senator was the epitome of a sensible Republican, the one who could cut a deal to get something done. Like his mentor Howard Baker, Alexander was always a party man, but he prided himself on making government work. 

Rolli spent a fair amount of time in Alexander’s orbit. She joined his campaign team and then his D.C. office in 2002 alongside chief of staff and longtime adviser Tom Ingram. After grad school and a job in Gov. Bill Haslam’s administration, Rolli returned to run Alexander’s 2014 reelection campaign, a disastrous race marked by Joe Carr coming within 9 percentage points of knocking off the senator in the primary. She was dismissed for the general election and returned to the Haslam’s Economic and Community Development office under Bill Hagerty, but she never stopped speaking fondly of her time working for Alexander. 

It’s notable in part because of Alexander’s disdain for Donald Trump. He tolerated and often voted with Trump’s policies during his final four years and even voted against his impeachment, but Alexander was not a Trump Republican. He called for Trump to admit defeat following the 2020 election and was critical of his flurry of legal attempts to overturn the vote. 

But in the world Rolli finds herself in while running for mayor, there are 100,000 residents who voted for Donald Trump in 2020, and Rolli desperately needs them to turn out if she is to pull off an upset against Freddie O’Connell. There’s not a giant, non-Trump Republican voting block out there: Hagerty, who succeeded Alexander as GOP senator, got 106,000 votes in the same election. 

Her message about crime and taxes is tailor-made for the Trump crowd, even if the details are a little squishy. The Metro police she praises, and whose union has endorsed her, have done a good enough job in the last year that crime is actually down in most major categories. She’s on the record saying the property tax increase that she’s so critical of affecting affordability will not be repealed in a Rolli administration. 

And then there’s the matter of Trump himself, a uniquely polarizing figure in U.S. politics.

When the Banner’s Demetria Kalodimos asked whether she voted for Trump or not, Rolli didn’t answer the question, instead lamenting, “You know, when we nationalize City Hall, it doesn’t really help Nashville, right?” Instead, Rolli praised Liz Cheney for beginning the country’s healing process.

Cheney, you’ll remember, was one of the Republicans who served on the January 6th Committee, which produced much of the evidence that prosecutors are now using against Trump in court. 

Kalodimos asked if she was a Liz Cheney Republican.

“Yeah,” Rolli said. “And I don’t think there’s any part of my background that would say otherwise, right?”

It’s a legitimately brave stance for a Republican to take, due to how widely Cheney is reviled within the Republican party right now. It’s also a middle finger to 100,000 Trump voters in Davidson County, many of whom still support the former president. Rolli can’t embrace Trump or the MAGA movement, which Republicans continue to do across the state, because it would likely incite the much larger block of Democratic voters here in Metro. But she needs them to win.

On Friday, O’Connell leaned into this with a piece of direct mail that included a photo of Rolli at Trump’s 2017 inaugural.

“Too much MAGA,” the mailer read. “Rolli said she was ‘Proud to be a witness’ to Trump’s inauguration.” The mailer attacked Rolli for hiring a campaign consultant linked to the Proud Boys. The consulting firm also represents a raft of far-right election deniers.

This is the Trump Tax in Davidson County. 

In the 2022 midterms, House candidates nationally who identified as MAGA underperformed other Republican candidates. Yes, Nashville’s election for mayor is technically a nonpartisan race, but Rolli self-identified as a Republican early to draw enough voters to make the runoff. O’Connell’s attack, whether or not it’s true, is designed to make Rolli pay a tax for being a Republican in Trump’s party. 

In 2015, David Fox didn’t have to pay this tax. When he came within 10 percentage points of beating Megan Barry, he was able to shrug off much of the criticism that he was a Republican because of his time on the nonpartisan school board. He was a known commodity and Donald Trump, as a politician, was not. Rolli is not as fortunate.

In his final years in office, Alexander was caught between the president he didn’t particularly care for and the party that Trump took control of. Rather than fight them, he chose to walk away. In her run for mayor, Rolli is now stuck in a similar dilemma. The question is whether she can do enough to turn out Republicans without the Trump Tax making a victory prohibitive.

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...