It’s well-known that Key West’s geography and character are considered unique for residents. Those calling it home know its politics are unique, too — as is first-term mayor, Teri Johnston. 

Johnston is running for reelection this year. Florida’s primary election is Aug. 18. With more than 50% of the vote, she’ll win outright. If not, the top two vote-getters will face off in November.  

The nonpartisan election has drawn two candidates running against Johnston, who is in the second year of a two-year term. 

Her opponents are Mark Rossi, a Republican business owner and former city commissioner; and Rick Haskins, a vacation rentals broker and also a Republican.  

Nonpartisan or not, it’s no secret that Johnston is a Democrat and Key West’s first lesbian mayor. She’s also only the second woman to ever hold the post. 

Early years 

Johnston, 69, was born and raised far from South Florida — in Conrad, Iowa. She describes the upbringing as “solid middle class.”  

Her father was an alfalfa plant manager.  

“He did that for many years until he retired and bought the only bar in Conrad,” Johnston said.  

Her mother died young at 43. Johnston is the second oldest of three sisters. 

She said being gay in Conrad wasn’t as suffocating as one might imagine. 

“For a tiny little town of 900 it was really progressive,” she said, “I don’t know why.” 

Even though Johnston dated in college, she said she didn’t really come out until a couple of years after graduation. 

“Although everybody that I hung around with were females,” she said chuckling. “At that point I think I was the last to tell my family; they all knew; it was like, duh.” 

Johnston said she had a very supportive family who would also embrace her eventual partner, Dar Castillo. Castillo was raising two daughters when they met. The couple now has grandchildren. 

Johnston earned a degree in physical education and a minor in political science from the former John F. Kennedy College in Wahoo, Nebraska, before moving around and eventually landing in Illinois for almost two decades.  

“I went [to JFK] because it was one of the first programs [to give] women’s athletics scholarships,” she said. 

Johnston was a three-time All-American softball player. 

Business, politics 

Like many have before her, she eventually spent a few winters in Key West and would permanently relocate in 2001. 

Johnston’s a longtime co-owner of a home design and construction company with Castillo. She previously worked for Hollister Inc. — a downtown Chicago-based health care equipment manufacturer — doing human resources, sales and management. 

Before running for mayor, Johnston spent eight years on the Key West City Commission — two four-year terms. She’s held several Monroe County board positions (planning, workforce housing) and has done nonprofit work, too.  

On the left of the political spectrum, she said it was interesting to work with colleagues in Republican-leaning Monroe. 

“But when you cross the county bridge which comes into Key West, it is very different,” Johnston said. 

Through the pandemic, Johnston has been in favor of buttoning down to make Key West safe and healthy. She said her opponents have been on the “other side of that coin.” 

Johnston was a force behind a strong mask ordinance and an early informational checkpoint for motorists coming into Key West. It was set up so that only those doing business in the lower keys would be let through, not day-trippers. 

“We were putting protective measures in place, getting staff trained and getting [personal protective equipment] to open back up slowly,” she said. 

Johnston said there was heat from the Republican side of the fence to open back up. Key West did that on June 1. She thinks it was too soon. 

“We had 41 [COVID-19] cases as of June 1, and two months later it was 540,” she said. “We’d like to get our positivity rate way under 10%.” (At press time it was hovering around 13% to 14%.) 

While there have been fewer than 10 deaths (as of press time), it’s worth noting that Key West is a city of about 26,000 year-round residents. 

“It’s not all tourists. It’s also within our community. Most of our spike can trace back to the Fourth of July — we didn’t have fireworks and closed the beaches but people had large picnics and family events. We saw a marked spike,” she said. 


Teri Johnston (center) during an unveiling of new public health signage. Photo courtesy of Teri Johnston.

A look ahead 

The campaign trail this time around has been different, with mostly virtual outreach to voters. 

And even though in Key West a mayor’s sexuality isn’t a huge focus for the average person, Johnston said being the first lesbian in the position is a nice milestone. 

“I’m very proud of it. We do have a different environment. But it is changing — the one human family is getting frayed around the edges because of the political environment. We’ve had a couple hate crimes in Key West,” she said. 

The city, which holds about $11 billion in property values, is also facing issues like sea-level rise. 

But even during the intensely divisive politics of the country and the massive pressures of the pandemic, Johnston is optimistic. 

“I’ve got three things to focus on: get our community healthy; reboot our economy; and put all of our people back to work,” she said. 

Johnston said that COVID-19 will transform tourist destinations like Key West. 

“We’re going to create an economy based on what we’ve been given, but I don’t look at it quite so negatively. We’ve got some smart, creative people here making adjustments. I think we’ll see smaller, more intimate groups and develop areas of Key West that we haven’t been able to. We’ve got incredible things in Key West and we’ll shine a light on those and allow other types of businesses,” she said. 

At press time, Johnston was preparing to soon take part in Key West’s three- and five-year strategic planning sessions.  

“I ran against 12 people last time,” Johnston said. “I hope I’ve done a good enough job, because this isn’t any time to have a novice.”