Shan Rose thwarted the political comeback of Regina Hill and Tom Keen ousted incumbent City Commissioner Jim Gray in Tuesday’s Orlando City Council elections, kicking off the start of what could be a wholesale turnover of city government in the coming years.
Meanwhile, voters in District 3 narrowed the five-person field to two, with Roger Chapin and Mira Tanna advancing to a runoff Dec. 9. The winner of that contest will replace retiring commissioner Robert Stuart.
Rose’s win came in the most tense and closely watched race in Orlando this year. She had won a partial term as interim commissioner last year after Hill was suspended from office following an indictment and arrest on seven felony charges.
Rose, who needed more than 50% of votes to avoid a runoff, took in 51.84% to Hill’s 33%.
“Thank you for giving me the privilege of serving you for four more years,” Rose said “I promise to keep listening, to be transparent, and to work with you every day to deliver results.”
Regina Hill, at left in center of photo, looks at election results during her party at Obsidian Cocktail Lounge in Orlando on Tuesday, Nov. 4, 2025. Hill lost her bid for reelection to the Orlando City Commission. (Stephen M. Dowell/Orlando Sentinel)
At her election night party, Hill told reporters she intended to go to the Orange elections office on Wednesday to review ballots and signatures.
Hill said she thought her criminal case was a factor in the outcome.
“You know, every moment I was being called a criminal, a thief or abuser …. and that wasn’t one news cycle, that was for almost two years, I’ve been identified as the person that harmed people — and it’s called conditioning,” she said. “But I think after the narrative that has been spent about me as abuser, a thief or liar or fraud, I think I did pretty good.”
Tension between the two had spilled over in recent weeks, after Hill accused Rose of being romantically involved with a registered sex offender, Travis Wright, whom she alleged Rose brought to city events attended by children. Rose notarized a request to vacate Wright’s original charge, which involved a pre-teen girl.
Rose wouldn’t say if she was dating Wright, and Hill said she didn’t have proof of the accusation. State records, however, suggest Rose and Wright are in business together.
Ultimately, voters in the district spanning downtown Orlando and neighborhoods west of Interstate 4 backed keeping Rose in office. She pitched her candidacy as a way to move past the drama.
Had Hill prevailed, it’s unclear if she would have been allowed to take office. She’s still facing the felony charges that led to her suspension and so far a trial date hasn’t been set. She’s maintained her innocence, and Gov. Ron DeSantis’ office didn’t respond to questions about her status.
Meanwhile, a major changing of the guard took place in southeast Orlando’s District 1 as Keen toppled Gray, who had led the city’s growth engine since first taking office in 2012.
Keen took in 54% of the vote to Gray’s 31% in a four-way race.
Keen said he was knocking on doors, reminding voters to sign up to vote by mail as soon as he filed. He noted he won the vote-by-mail count.
“The [council] is going to have a big change in the next two years,” he said, noting Dyer’s planned retirement and other commissioners weighing their futures. “People want to know that they’re being heard, and that’s my goal.”
Keen, who briefly served as a state representative last year in an area including the city council district, lined up a slate of influential endorsements from most of the region’s progressives, including U.S. Rep. Maxwell Frost and State Rep. Anna Eskamani, the lone candidate so far for Orlando mayor in 2027. Progressive political committees also backed Keen at $1,000 apiece.
The officially nonpartisan race turned into a partisan clash, which ultimately favored the Democrat Keen over the Republican Gray. The district has about 2,400 more Democrats than Republicans, though the largest share of its voters belong to neither party.
Florida’s Republican Party sent an ad last week to voters urging them to keep Gray in office as Orlando’s last GOP member on the council, where he was “surrounded by liberals.” He was also backed by Mayor Buddy Dyer and Commissioner Tony Ortiz – both Democrats.
The state GOP spent more than $27,000 to back Gray in recent weeks, campaign reports show, including $15,000 in “professional consulting” and $12,628 on mail advertisements.
In the northwest area of Orlando in District 3, Chapin and Tanna, with just 13 votes separating them, head to a runoff off Dec. 9.
In the five-person field, Chapin received 2,477 votes to Tanna’s 2,463, both coming in at about 34%. Chapin, the son of former Orange County Mayor Linda Chapin, was the best-funded candidate in the race and had the endorsement of Dyer and Stuart, both residents of the district with deep roots there.
Chapin, who raised nearly $220,000, said he had been expecting to be in a runoff and was preparing to get back to talking to voters for another month.
“You kind of start over and focus on your messaging and focus on your voters,” he said.
Tanna, who raised about $64,000, thought her transit-focused message resonated.
“People want safe streets where they can walk and bike safely, they want alternatives to where not everybody has to own a car and they want relief from traffic congestion,” she said.
Across the three districts, 15,033 ballots were cast. All results are considered unofficial Tuesday night, until the canvassing board convenes on Friday to certify the results.