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Port Otago chief executive Kevin Winders said the 72-year-old brick Waterfront Industry Commission building had a deteriorating asbestos roof, and the cost of replacing it appeared prohibitive.
The company would not make a final decision until closer to Christmas, at the earliest, but two clubs using it had already been relocated, he said.
"Our view is at the moment that it [the building] will come down," he said.
That concerned Maritime Union of New Zealand Port Chalmers branch president Tim Camp, who said the building "may not be seen as a historic building, but there’s a lot of history in the place".
The building, known as the "bureau", has been the home of large union meetings, public gatherings, community clubs and fundraising efforts for more than 70 years.
It was built in 1946 to provide facilities for waterfront workers as they waited for casual work each day.
Since then, it had been the Port Chalmers epicentre of the 1951 waterfront dispute, and again during waterfront confrontations in 2000-01.
But it had also become a venue for fundraising drives to support the families of waterfront workers killed on the job, and to pay for medical equipment, including a CT scanner, at Dunedin Hospital.
"I think it would be a major loss to the community," he said.
Former union branch president Dave Dick agreed, saying the history on the walls — including that of his own family — was "just way out of the bloody world".
"A lot of things have happened here."
Former Waterfront Workers Union national and branch president Bruce Malcolm said the suggestion of demolition was a "bloody disgrace".
"I couldn’t believe it.
"They should just pull their silly heads in . . . and leave the place alone," he said.
Mr Winders said fresh concerns about asbestos inside the Fryatt St sheds, which were to be removed, had prompted a review of the rest of the company’s property portfolio.
That included three other buildings already known to have asbestos issues, including the WIC building, he said.
A workshop with asbestos could be rectified, but the WIC building and a second building on the Port Chalmers wharf — known as the "elephant house" — were more problematic, he said.
Both would probably have to be demolished, as the $215,000 cost to the Dunedin City Council of removing the nearby Sims building’s asbestos roof showed what was required to save them, he said.
The company needed to balance community and heritage interests with the operational requirements of the port, which was "always a difficult one", he said.
"I can understand it’s been a large part of the union movement in that area. Hopefully we can work our way through that and relocate the union ... to some alternative premises.
"We’ve got some lovely buildings in Port. There’s still plenty of heritage buildings there."