Leary is in his second term as mayor of the city, which has approximately 30,000 residents. He and his wife have 14-year-old triplets, and they own a small manufacturing company and a property management company.
Bonilla was initially considered a long shot when she was elected to the District 5 seat in 2016, raising just over $38,000 in campaign contributions.
Bonilla is also the chair and treasurer of Residents United for Rural Area Longevity (R.U.R.A.L), an Orange County political committee she formed in April 2018.
Bonilla filed for re-election back in October 2018, and already faces one challenger, Anjali Vaya of Winter Park, who filed on Aug. 7 of this year. Leary's filing is dated Aug. 16, and a third challenger, Sonja M. Speadling, filed on Sept. 17.
By the end of last month, Bonilla reported raising $24,425 and spent $10,991 on her re-election so far. Leary raised $98,325 in his 2018 mayoral re-election campaign and $128,645 in his first 2015 mayoral race.
Leary's campaign went on to quote a FloridaPolitics.com ranking of Central Florida’s most powerful politicians, which noted the mayor “has quietly undertaken the transformation of that city from being Orlando’s most venerable suburb to being perhaps Central Florida’s most admired city for its future prospects and has done so in one of the toughest political environments in the region.”
"I'm especially proud of our efforts to increase and improve green space in the City, provide additional and better recreational amenities for residents and guests and responsibly manage growth in Winter Park," said Leary in a statement on Tuesday.
Leary touts his leadership experience among his qualifications, including service on the Florida League of Mayors Executive Board, as chair of the Orange County Council of Mayors, and twice being named a "Home Rule Hero" by the Florida League of Cities, as well as "appointing hundreds of individuals to citizen advisory boards."
"Residents deserve elected officials who are committed to working in an inclusive and collaborative manner with one another, and constituents, to responsibly manage the challenges that come with the region’s explosive growth," said Leary in the statement.