The building from which Arthur Scargill once controlled the National Union of Mineworkers (NUM) could be pulled down.
The building has been a Sheffield landmark
Plans to replace the office block in the centre of Sheffield with housing go before councillors on Monday.
It was built for the union in the 1980s when Mr Scargill decided to move the its headquarters from London.
But with the decline of mining, the union withdrew to the old Yorkshire NUM headquarters in Barnsley with the Holly Street building remaining unused.
Originally, the modern headquarters also included the historic Water Works Company office fronting onto Division Street.
But this was separated off in the 1990s to become a bar.
Officials at Sheffield City Council are recommending councillors should approve the demolition of the disused building as part of a regeneration scheme for the area near the City Hall.