In 2007, a team of Seattle consultants assessed the historical significance of dozens of buildings in the city’s urban core. Some were deemed meaningful enough that they were nominated as local landmarks. Others weren’t so lucky.

One building in the latter category was the Showbox, a downtown music venue that opened in 1939. Although its walls were virtually dripping with rare memories from nearly every musical genre since the Jazz Age, its physical structure had been altered multiple times. As a result, the consultants deemed that the space wasn’t qualified to be a historic site.

That decision, made in the early days of Seattle’s rapid redevelopment, paved the way for a fierce battle that’s playing out today. The venue’s property has since been upzoned and set to be sold and demolished. That sparked a passionate campaign to save the Showbox, and even prompted the city to take extraordinary measures to protect it in the short term. At stake is the Showbox venue itself, which is set to be replaced by a high-rise apartment building. Also at risk, depending on who you ask, is a key component of the city’s cultural history and the integrity of the city’s management of development. On all sides, it seems the outcome hinges on one question: When is it too late to save a valued institution?

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Last summer, news broke that the owner of the Showbox would be selling the property. The buyer was a British Columbia company that intends to replace the music venue with a 44-story apartment tower. From the start, many residents and music lovers were outraged, arguing that the musical history and memories within the venue’s walls could not be replicated, and therefore need to be protected.

Just steps from the iconic Pike Place Market, the Showbox is one of the last remaining venues from Seattle’s musical heyday. It has featured performances by local breakout stars, such as Macklemore & Ryan Lewis, touring icons like Duke Ellington and the Ramones, and a wide array of hometown bands like Pearl Jam and Mudhoney.

“The venue has a certain magic to it,” said Jay Middleton, whose old band, Before I Die, performed there about a decade ago. “I’ve arrived early for load-ins just to sit in the green room so I can try and feel ghosts. Kind of weird to say, but there is a presence in there.”

Showbox supporters have organized rallies and concerts, and created thousands-strong Facebook groups dedicated to saving the venue. And when Middleton launched an online petition urging the city council to intervene, more than 100,000 people from across the world signed it. Some high-profile musicians have contributed to the efforts, too: During Pearl Jam’s Seattle concert in August, members of the band talked about how important it is to save the venue.

“There’s more great shows that I’ve seen, legendary acts, legendary bands, legendary people, legendary nights in that one venue here in Seattle than brain cells that I have left in my head,” frontman Eddie Vedder said during the show.

But the movement to protect a space and its memories is up against a harsh reality. The Showbox property has been zoned for high-rise redevelopment for more than 20 years. Previous attempts at historic preservation didn’t pan out. And just last year, the city upzoned the property to allow for 44 floors, according to a lawsuit filed by the company that owns the Showbox. Seattle, in the midst of a housing crisis, desperately needs more housing, and the proposed tower would provide more than 400 units for people to live in, plus contributions of about $5 million to a fund for affordable housing.

“If the city wanted to preserve the Showbox or thought that that side of First Avenue was important to preserve—and I personally think it is—then the city shouldn’t have put in place the zoning” that allowed for this type of tower, said Pat Schneider, a land use attorney in Seattle.

Indeed, the city is now signaling that the Showbox is worth preserving. In August, after the sale was announced, the Seattle City Council intervened, temporarily adjusting the boundaries of Pike Place Market Historic District so that it included the Showbox. That meant that for the next 10 months, any changes made to the theater have to go through the Pike Place Market Historic Commission.

Roger Forbes, who has owned the property since 1997, responded by suing the city for $40 million, the amount he claims his company would lose if the sale doesn’t go through. He argues that the boundary change violated state constitutional rights of due process, freedom from uncompensated takings of private property, and freedom of speech, among other claims.

In a hearing last month, a King County judge threw out two of these claims, including one arguing that the city council’s decision constituted an illegal taking of private property. The case is now set to go to trial in August.

No matter what decision is reached there, it’s clear the issue comes down to timing.

The city has the underlying authority to create historic districts and adjust their boundaries. Had that been done years ago, as some had suggested, this situation might have been avoided.

Its leaders also have the authority to adjust zoning in its comprehensive plan. Had they declined to allow high-rise development at the Showbox site, tearing down the building might have been less enticing.

“The city is now trying to say, ‘Oops we made a mistake,’ after people have invested and relied upon the zoning,” Schneider said. “Then this is what you get in response. You get lawsuits.”

The frustrations over the Showbox are emblematic of tensions that happen in such a rapidly changing place. As the fastest-growing city in the U.S., Seattle has added 114,000 residents since 2010—a 15 percent increase. For the past three years, its skyline has had more cranes than any other city in the nation. The glass towers they’re building are often replacing old, treasured buildings.

“In Seattle’s current real estate market, there is too much loss of beloved historic places,” said Naomi West, a moderator for one of the Showbox Facebook groups. “The Showbox’s history and its use as a home for music are just too important to lose, and that’s why so many people came out so quickly to oppose its demolition.”

In this context, the Showbox is an obvious flashpoint. For longtime locals, it’s a powerful source of nostalgia, especially as the area around it has become less familiar over the years. For developers, it’s the definition of prime real estate. And for the city—if it’s truly the cultural icon that many say it is—it could prompt a moment of reflection about what’s worth saving, and how late is too late to make that clear.