Mesirow aims high with Aspen aspirations |

Mesirow aims high with Aspen aspirations

Councilman Skippy Mesirow, during the election season. Monday was a lighter and lighter-hearted day for the council.
Austin Colbert/The Aspen Times

Aspen City Councilman Skippy Mesirow shows no sign of backing off high idealism, lofty visions, and a big taste for finding new solutions. Not even the onset of a lockdown pandemic soon after joining the council with all its hard, practical lessons could stop that.

“It was really frustrating for me,” Mesirow, 36, said. “It was really hard. We didn’t have a city manager; we had COVID. I didn’t really know what I was doing. And there’s a lot of frustration.”

The shuttered buildings in the core of Aspen and red tape on construction have specifically plagued the city during Mesirow’s first term.

“But in the last year and a half, we have really gotten a lot done for this community. But it’s just the start because in my observation, we have inherited an incredible legacy of leadership with doing the hard things,” he said. “But the architecture on which we know some of the most important things — we need affordable housing, local business, ease of congestion, healthier environment — our current architecture cannot get us there. We need new approaches.”

Currently the youngest member of the City Council, he seeks re-election as his first term ends to become part of the new beginning he envisions.

Lifelong Aspen Connection

His Aspen roots run about as long as he has been alive. His grandparents bought a house here in the 1950s, and he was on skis by 18 months old. Mesirow would visit often from his hometown of Highland Park, Illinois, and moved here in 2004.

After graduating from the University of Colorado, he returned to Chicago as an unpaid intern for the deputy director of the Obama for America presidential campaign in Illinois and four neighboring states. At 23, he was the campaign manager for Jesse White’s successful race for Illinois secretary of state in 2010.

In Illinois, four of the past 10 governors have been incarcerated for committing federal crimes during their time in office, one disillusioning fact among many in politics.

“I was in the middle of the Rod Blagojevich scandal at one point,” Mesirow said. “And all the glitter that initially drove me to get into public life fell off.”

So he left what he considered a promising political career and embarked on a nomadic lifestyle.

“I would say traveling has been my graduate school in so many ways. I have traveled to very unconventional places, such as Russia, North Korea, Vietnam, Iran, the West Bank, tribal territories in rural India, and always with the intention of studying different people, culture, and societal frameworks,” he said.

During this time, he launched two unsuccessful businesses, which he said gave him invaluable experience. His thinking began to change then, and today, a wider world perspective shows up in his campaign platform.

“The most amazing city centers across the world are all walkable,” Mesirow said. He said visiting cities has given him the intellectual flexibility to be open to new and differing systems. “That’s why I’m pushing for this government office of innovation,” among the ideas he would seek to implement early on if re-elected.

“And when I’ve seen what they have done in the city of Vancouver with vacancy tax and how it’s working, it makes me believe we can build three Lumber Yards without investing a single dollar if we use a similar tax structure,” he said.

Mesirow was a co-founder, two term chair, and member of the Aspen Next Generation Advisory Commission from 2013 until last fall, according to his LinkedIn site.

“As I was back here and working in a variety of different ways, I just sort of got dragged back in unexpectedly; someone asked me to go to a city meeting about getting young people involved in politics.” he said. “It was a white-boarding session that turned into the Next Gen Advisory Commission. And we worked on a variety of issues bringing meaningful change in affordable housing and promoting childcare and voter participation.”

One of their projects was passing an election-ballot initiative in 2018 to change the municipal elections from May to March.

“That resulted in the highest number of voter turnout for Aspen (in 2019), an increase of 26%, which was really important to us,” he said. “I just had a variety of experiences that kind of re-ignited my recognition that at the local level, we can really make change.”

The infamous Lift One proposal was on the ballot, as well, in March 2019, and Aspen’s turnout soared to nearly 60%. By the 2021 municipal election, however, turnout had returned to the longstanding trend of around 40%.

In 2021, Mesirow founded the Elected Leaders Collective, a company bringing tools and a community of mental health and well-being to mission-driven, public-sector workers. A life mission is to heal politics, he said.

There’s also his other investment, his full income-bearing job.

“I run a vacation rental company called SkyRun. We just help second-home owners use their homes when they’re not using them,” he said.

Looking Ahead

“We have incredible staff and expertise to call on,” Mesirow said. “The question is, can we be tied to revenue reverential of and connected to the through line to the original Elizabeth Paepcke vision of Aspen? And can we be broadminded and curious enough to seek out new solutions to try to achieve old ends to meet a new moment?”

He said serving a term on the council is the most applicable resume for the position.

“Certainly nothing else can really prepare you,” he said. “I have been intimately involved in policy, politics, and campaigning, and this community my entire life.”

Experience matters, then, but he remains fixed on big, new ideas.

“I am putting out bold policy proposals to move us out of the architecture of the 1980s and in some cases, 1780s, so that we can solve problems for the next generation and things that this council either doesn’t agree with or hasn’t considered. I’m actually putting out new ideas,” he said.

He said he has a record of being for the community first in outlook, even when that may go against personal or professional self interests.

“I demonstrated a willingness to act independently for the broad community benefit. And I’ve done that many times,” he said, “in many ways. So I think I have that proven track record.”

Mesirow lives with his partner Jamie Butemeyer in Aspen. He is out in the city door knocking on weekends and plans a variety of community events and fundraisers. Visit for more information.