For the first time in 15 years, Chaska has a new mayor.

Taylor Hubbard took up the gavel in Chaska City Council chambers Monday night after taking the oath of office. Hubbard defeated George Glaros, Jr. in November to replace long-time Mayor Mark Windschitl who opted not to run for re-election last year. In doing so, Hubbard becomes only the second female mayor in Chaska’s history.

“I’m not intimidated by it,” she said. “When I do something, I’m pretty much all in.” 

From concerned citizen to council member

Hubbard grew up in the Chanhassen area and attended Chaska High School, graduating in 2000. She and her husband Martin rented a home in Chaska nearly two decades ago and quickly fell in love with the town.

“We knew we wanted to buy a home in Chaska,” Hubbard said. Eventually, they found a place in a neighborhood northwest of Bavaria and Engler.

It would be that home that would lead Hubbard to get involved with the city as she stood before the council alongside her neighbors to express concern over plans for the baseball fields at Sunset Park.

“Looking back, we feared the worst, but there were a lot of positive outcomes,” she said.

One of those positive outcomes was a council member reaching out to Hubbard to encourage her to get involved with one of the city’s commissions. She did, spending six years on the Chaska Human Rights Commission from 2008 to 2014.

And when former Councilor Greg Boe was elected to serve as a state representative in 2018, leaving an open seat on the Chaska City Council, Hubbard, by then a mother, tossed her hat into the ring.

“I thought it was a really interesting, unique opportunity for me to fill a perspective hole,” she said.

The city held a special election the following May and Hubbard bested Nate Bostrom to represent Chaska’s Ward 2. In her five and a half years as a council member, Hubbard says she learned a lot.

“At first, it was learning the jurisdictional and planning process,” she said. Then, it became a series of lessons in customer service.

“I had to put myself in other people’s shoes,” she said. “I never want to be the person that disregards someone who has a concern. The challenge is balancing those needs with the needs of Chaska as a whole.” 

Finding balance

Hubbard said the Highway 41 reconstruction project in downtown was one of those balancing issues.

“(Highway) 41 is so challenging in the sense that there are obstacles. It’s a state highway running through a historic downtown, buffered by a river,” she said. “It was also economically challenging for our businesses. There was an intense amount of pressure.”

As a small business owner herself (Taylor Hubbard Photography in downtown Waconia), Hubbard empathized with the difficulties the downtown community faced. With the project now in its final stage, Hubbard is optimistic about the opportunities ahead.

“Now, we look forward to the future,” she said. “That is my focus.”

Hubbard said in talking to Chaska residents on the campaign trail, she heard plenty of hopes for downtown.

“They want to shop more, dine more,” she said. “I’m going to champion that. I want to be a partner in that.”

As a photographer by trade, Hubbard sees parallels between her day job and the job of mayor.

“I’ve spent my whole life celebrating people,” she said. “This is just a different way of interacting with people. Now I get to help make a community great.”

Hubbard lauded Chaska’s many notable amenities like its robust trail system and the curling center and highlighted the latest addition of The Loop, a revamped golf course with disability access at the forefront of its design.

“It’s such a unique concept and amenity that met the principle of what Chaska stands for,” she said.

The goal for the future is to keep the standards high in Chaska, whether it’s looking for more unique amenities or making sure city services are maintained.

“I want to see that Chaska stays an amazing community with great services,” she said.

That means supporting future facilities projects that address aging infrastructure including the municipal services building, the library and City Hall. 

“I want to be a good steward of our budget, but not overdo anything,” Hubbard said. “We are almost fully developed so it’s a hard road to walk.”

In the end, Hubbard said she will try to do what’s best for the community, but she hopes that in communicating the “why” behind everything, the community will at least understand the council’s rationale for their decisions.

“It doesn’t always minimize the pain, but if we’re strong in our communication, there’s a transparency that comes with that,” she said.

Hubbard encourages residents to interact with her.

“Come up and say hi,” she said. “I’m always available to have a conversation. I welcome the negative and the positive. If we don’t agree, that’s ok. Let’s talk about it.” 

Making history

Hubbard’s mayoral win means that she becomes only the second female mayor in Chaska’s history. Tracy Swanson was Chaska’s first female mayor, serving from 1979-1984.

“I know I have big shoes to fill,” Hubbard said.

The history making doesn’t end there, though. Hubbard will preside over the five-member council with its first-ever female majority. Newcomer Leah Sheveland (Ward 4) will join veteran council member McKayla Hatfield (Ward 3) on that majority with newly elected Joshua Benesh (Ward 2) and veteran Jon Grau (Ward 1) rounding out the 2025 council.

Hubbard also joins a growing consortium of female mayors in eastern Carver County including Chanhassen’s Elise Ryan, Carver’s Courtney Johnson and Victoria’s Debra McMillan.

“I think it’s fantastic to see women lead each of the communities in Eastern Carver County,” Johnson said. “Representation is important, and I think it’s great to see more women getting involved in local government.”

“In order to best represent the communities we serve, I think it’s important for elected leaders to look like the people in those communities,” Johnson continued. “That includes women and other groups that are traditionally underrepresented.”

“Diversity of thought is what creates a strong democracy and the best policy,” said Victoria Mayor McMillan. “Each person brings a different background, perspectives and experience to their role. That is true of any mayor or leader — regardless of gender.”

Hubbard is proud to represent female voices on the council, though she understands there can be a double-standard when it comes to gender. She said that she has already experienced a few things during her time on the campaign trail that she doesn’t believe a male candidate would have faced.

“I don’t use that as an excuse, though,” she said. “I recognize it, and I ask how do I move past it.”

Hubbard is determined to be a good leader for Chaska. “I hold myself to a really high degree of integrity,” she said.

“Taylor has great experience as a council member that will serve her well as she moves into the mayor’s seat,” McMillan said. “There are hard days as mayor, but it is always, always a great privilege to serve your community.”

Hubbard is ready for the new challenge. “There have been a lot of steps already walked on this literal and figurative journey.”

And to anyone that doubts her abilities, Hubbard says this. “My mom would say I get no greater pleasure than proving people wrong.”