By all accounts, Tulsa Mayor G.T. Bynum has been a fast-rising political star in Oklahoma.

Part of a political dynasty whose uncle, grandfather and great-grandfather all served as mayor of the state’s second-largest city, the mild-mannered, bespectacled 43-year-old worked as a staffer for former U.S. Sens. Don Nickles and Tom Coburn, both GOP icons in the state.

He defeated a fellow Republican in the nonpartisan mayoral race in 2016 in part by reaching out to the city’s Black community. Many assumed his reelection this year was all but automatic.

But as the election approaches Tuesday, Bynum finds himself under attack from both the left and the right in the city of 420,000, and wounded by mistakes that have presented a possible opening for one of seven challengers hoping to unseat him.

His struggles to keep his balance illustrate some of the strong political crosscurrents being thrown off by the pandemic crisis, along with tensions over racial justice and President Donald Trump’s reelection bid, in urban areas in traditionally conservative places.

Among Bynum’s challengers is a young Black community organizer, Greg Robinson, whose last-minute campaign has generated a buzz in a longtime Republican stronghold that is increasingly seeing Democrats win local races.

Robinson, 30, who grew up on the city’s predominantly Black north side, returned to his hometown to help found a nonprofit after working on President Barack Obama’s reelection campaign in 2012 and for Hillary Clinton’s campaign in 2016.

Once a Bynum supporter, he said he has become convinced that the mayor will never go far enough to make the city as progressive as it should be.

“We have been failed too many times by a mayor who continues to bend to the Fraternal Order of Police or to President Trump as opposed to standing on the side of the people of Tulsa,” Robinson said. “I just felt like in the moment that we were in, not just in the city of Tulsa, but also across the country with people demanding to have their humanity recognized … it was time in Tulsa to give us a choice.”

Bynum said he’s trying to follow the model of his grandfather, Robert LaFortune, who ran the city from 1970 to 1978, and who insisted on listening to arguments from all sides before deciding an issue.

“It has been a very hard four years to navigate that, especially when there are so many opportunities for division out there,” he said.

Bynum has a hefty financial advantage in the race, reporting more than $600,000 in contributions, and the endorsement of many organizations, including the Tulsa World, the local newspaper. But Robinson’s $215,000 is substantial for someone who wasn’t widely known. He has mounted a vigorous direct mail campaign and his signs now sprout in the mid-city neighborhoods where many white professionals live.

Tulsa is among a group of transitioning cities in America’s red states that are separating politically from the deeply conservative rural areas around them. In the 20th century, the city was dubbed the “Oil Capital of the World” and boasted some 400 oil companies, large and small. Tulsa also was home to the state’s wealthiest African-American community, a southwestern Harlem of sorts called “Black Wall Street” where prosperous merchants, doctors and entrepreneurs thrived. In the worst scar on the city’s history, a white mob burned the district in May 1921, killed several hundred residents and left thousands more homeless.

For decades traditional corporate conservatives dominated Tulsa’s government, but Bynum and several local philanthropists have pushed to address the racial legacy and make the city more vibrant and economically diverse. Billionaire oilman George Kaiser funded an acclaimed $465 million public park and other public amenities, and offered cut-rate housing to attract young entrepreneurs. Bynum has recruited foundation money for health and education projects in the city’s Black community and spearheaded a $640 million tax package for community improvements.

But the remarkable mix of bipartisan support Bynum earned for the efforts took a serious hit when Trump chose Tulsa as the kickoff for a new series of campaign rallies in June. Bynum attempted to tack a middle ground, discouraging the rally and refusing to attend, but also refusing to shut it down despite warnings from health officials about spreading the coronavirus. The rally “ likely contributed ” to a surge of positive coronavirus cases in the weeks that followed, the city’s health director later said.

One of Bynum’s top aides, Jack Graham, resigned over his reluctance to require stronger health precautions.

“I don’t believe you can tell the president: ‘No, you can’t do it,’ but what I saw was no one acting with integrity to protect the citizens of Tulsa,” said Graham, who said he still plans to vote for Bynum on Tuesday. “Whether it was disregarding (Centers for Disease Control) guidelines of social distancing and requiring masks to be worn indoors or requiring hand washing stations.”

Bynum’s relationship with the Black community, which is about 16% of the city’s population, became strained when in a national television interview he blamed drug use, not race, for the police shooting of an unarmed Black man, Terence Crutcher, in 2016. He later walked back the comments and apologized. He also hasn’t delivered a new independent review system for police shootings after resistance by the police union.

“He has lost a lot of good will in our community,” said the Rev. Robert Turner, pastor of the African Methodist Episcopal Church in the city’s historic Greenwood District. “He ran a great campaign (in 2016) and touched the hearts of a lot of African Americans, but there have been several missteps.”

At the same time, Bynum’s response to the worsening coronavirus pandemic inflamed conservatives, who expected a fellow Republican to be less proactive. His early order closing businesses and requiring masks brought accusations that he was a political “snake in the grass.”

“I would say G.T. Bynum is the most left-of-center that he could have been in terms of his actions as it relates to the lockdown,” said local businessman and self-described “constitutional conservative” Clay Clark, a plaintiff in a lawsuit filed over the mask mandate.

For a politician who had a remarkably broad coalition for such a polarized time, Bynum’s fall from favor has been stunningly swift, said Democratic political strategist Michael Whelan, who said he considers Bynum a friend.

While many expect Bynum to win reelection, he has been diminished.

“It’s been heartbreaking for a lot of folks that he seemingly forgot who got him there. Without the Democratic coalition, he would not been elected mayor,” Whelan said. Some, he said, “felt tricked that the person we were sold in the last election isn’t really the guy we ended up getting.”