Will Denver finally elect a woman mayor?

Mary DeGroot came awfully close to a historic upset.

Flashback: Running for Denver mayor in 1995, DeGroot, a city council member, topped incumbent Mayor Wellington Webb during the May election by just 97 votes.

• But she came up short. Webb handily won the runoff election the next month.

Why it matters: DeGroot is the last candidate to come close to reversing a perplexing truth about Denver: We've never elected a woman as mayor in the city's 164-year history.

What's new: Five women are eyeing the opportunity to be a pioneering mayor in Tuesday's election.

• A few women are top-tier candidates who are vying for at least one of the two spots in the inevitable June runoff.

What they're saying: "I think that there is very much a power structure here that has controlled the political system for a long time, and largely those folks are men," former mayoral candidate Jamie Giellis tells Esteban.

• She believes Denver has a "real shot" at electing a woman this time.

What's happening: At-large Denver City Councilmember Robin Kniech said fundraising can be a challenge for women, especially when the top-dollar donors in the city are men.

• Kniech, who has served three terms, said it was challenging to "crack" into donors with deeper pockets, who were often men. “I think those barriers still exist for women trying to succeed,” she says.

Between the lines: Kniech said it's a stereotype that women are caretakers — but it's one she said is rooted in the factual, disproportionate burden women face to be one.

• Kniech said it's something some women candidates consider. "I think any woman who is living in our world understands that caretaking is not yet 50-50," she adds.

Zoom out: Colorado has also never elected a woman governor or U.S. senator. "For some reason, women have had trouble getting elected to executive positions in Colorado," DeGroot tells us.

Of note: The first woman to run for mayor in Denver was Antoinette Hawley in 1901, according to Denver Special Collections librarian Alejandro Hernández.

• She was part of an all-woman, pro-Prohibition ticket. Hawley finished fourth.

Go deeper: Six Colorado women who shaped the state's history