When Brian Jennings purchased Number One Fifth Avenue in 2019, he did so to preserve the historic Hillcrest gay bar for future generations. Shortly thereafter, he was confronted with a major decision.

A development firm had purchased a neighboring property — an eyesore that had been vacant since 1985 — and was planning to build apartments. The firm approached Jennings and his business partner asking if they were interested in selling.

Despite the opportunity to earn a quick profit on their investment, Jennings said they weren’t interested. He supports more housing coming to Hillcrest, but not at the expense of its history and culture.

“There has been a pattern where these neighborhoods that are being built up by the LGBTQ community become much higher quality than how they started,” Jennings said. “When the gentrification happens, a lot of these institutional bars are not in a position to be able to withstand the influx of new residences.”

While another loss of one of San Diego’s gay bars was averted, the threat of displacement remains. That’s why city planning officials and Hillcrest activists are working to establish an LGBTQ+ cultural district that they hope can balance the need for more housing with protections for the neighborhood’s nightlife.

The cultural district is one element of the Hillcrest Focused Plan Amendment, a long-term growth plan that is expected to go before the City Council this summer. The latest draft of the plan was released last month. Public comment on the plan is open until April 29.

The cultural district calls for public art honoring the LGBTQ+ community’s history in Hillcrest. Landlords of new developments would be required to disclose to their tenants that they’re opting into a historically LGBTQ+ neighborhood that can get noisy on nights and weekends. And legacy businesses would get first dibs on new commercial spaces if their property gets redeveloped.

The push for the cultural district began in 2022, after the City Planning Department had proposed an LGBTQ+ historic district. Businesses and nonprofits argued a historic district would stifle new development in Hillcrest while failing to protect the things that really matter.

“The historic designation is much more about brick-and-mortar buildings, and the cultural district is much more about people and a culture that has been created here over the years,” said Susan Jester, a longtime lesbian activist and fixture of Hillcrest who has been advising city planners.

The Hillcrest plan still includes a historic district, but city officials agreed to ease some of the restrictions on new development in the neighborhood’s core.

Jester said Hillcrest’s bars and nightclubs are more than just places to go drinking. They have been refuges for LGBTQ+ people, who, even today, can face violence for living their lives in public.

“I couldn’t go down to the Gaslamp Quarter or anywhere else in town to dance with my partner in 1980, but I could come here,” Jester said. “Same thing with mourning a lost friend or organizing our community … It’s sacred ground to us. And we want to keep it, not just for us and for the history, but going forward so that young gay people, LGBT people, come here and continue to feel that this is a safe and protected spot for them.”

The most controversial changes the city is proposing for Hillcrest are new allowances for high-rise buildings — though such developments would have to include new public gathering spaces, such as mini parks and plazas. Parts of the neighborhood would continue to be restricted to single-family homes and duplexes.

Still, the proposed zoning changes are too extreme in the eyes of some residents in and around Hillcrest. Residents in neighboring Mission Hills have threatened to sue the city over the plan, though previous lawsuits to block denser housing in the area have mostly failed.

City planning officials say Hillcrest’s walkability and proximity to public transit and major employers like Scripps Mercy Hospital and UC San Diego Medical Center make it a prime location for high-density housing.

Jon Anderson, a renter in Hillcrest who has been advocating around the Hillcrest growth plans, said more housing, paired with the planned improvements to bike, pedestrian and public transit infrastructure, will make it easier for new residents to live without a car — like he does.

“If you build these high rises and you have the transportation network as it’s being proposed in the plan, people will move here and they won’t bring a car, or they might only bring one car,” Anderson said. “That’s going to be what allows the neighborhood to retain the charm that it has now, I think, while still bringing more people into the neighborhood to be able to afford to live here.”

Anderson said most of the new apartments in Hillcrest are out of his price range, but that they can still ease the demand for the neighborhood’s older homes that are more affordable. He lives in a one-bedroom apartment built in the 1940s.

“When I went to renew (my lease), there were enough other vacant units in my building that they tried to raise my rent, and I was able to ask them not to, and they didn’t,” Anderson said.

The new apartments next to Number One Fifth Avenue range in price from $2,450 per month for a studio to $4,889 per month for a large two-bedroom apartment. The developer is offering up to six weeks of free rent — the type of incentive that is increasingly common as the housing market floods with new supply.

Sixteen balconies in the new complex open up directly onto the bar’s back patio, which frequently hosts late night karaoke, dance parties and drag shows.

In an effort to get ahead of potential conflicts with neighbors, Jennings said he is spending several hundred thousand dollars to enclose the patio and contain its noise.

“It’s one of the largest investments that this bar has ever seen in history,” Jennings said. “We’re taking a big risk, but we believe that we can make it work.”