Since the popularity of high-rise living began to wane in the 1970s, the housing scheme has been allowed to decay.
Although it has become one of Scotland's most culturally diverse areas in recent years, it cannot be denied Sighthill has long been in dire need of major investment.
Only five of the high- rises in Pinkston remain standing, with the five in the Fountainwell side of Sighthill having been pulled down in 2008 and 2009.
Three of the five blocks in Pinkston were marked for demolition soon after, but a campaign by residents convinced Glasgow Housing Association to save Pinkston Heights and Crawfurd Heights.
If the £250m transformation is approved at next week's meeting of Glasgow City Council's executive committee, these two will also come down.
Council leader Gordon Matheson said: "Let's not kid ourselves. This is an area that has been going downhill for many years.
"It deserves a lot better and that is exactly what will be provided now.
"This is the right thing to do. It's a generational opportunity and anyone in my position who had the option of £250m of investment for Sighthill would do exactly what I am doing – welcoming it with open arms."
The idea to completely transform Sighthill was first mooted in 2006 when a 20-year plan was announced.
Thousands of newsletters were distributed to residents, informing them of proposals to flatten the 10 high-rise blocks that existed at the time and replace them with 1200 private homes and 800 houses for rent.
A new street design was included in the plans, along with shops, business space, an improved Sighthill Park and possibly a hotel.
But the plans announced today, as part of the 2018 Youth Olympic Games bid, bring these changes forward by about 20 years.
Like most of the high-rise communities built in the UK during the 1960s, Sighthill was considered a desirable place to live and benefited from its proximity to the city centre.
But as high-rise living went out of fashion, the area was soon tarred with a stigma that meant fewer people considered living there.
By the mid-1970s, there was low demand for the flats – many lay empty.
In the late 1990s, Sighthill was chosen – along with the nearby Red Road in Royston – for housing asylum seekers and refugees. This led to some racial tension in the area.
A spate of racially-motivated attacks came to a head in 2001 when Iranian refugee Firsat Dag was stabbed to death at the Rainbow Bridge over the M8, having lived in Sighthill for only two weeks.
Despite those troubles, the people who still live there maintain a strong pride in their community.
Having convinced GHA to save two of Pinkston's high-rise towers, locals will today learn that their flats will be demolished after all.
Mr Matheson said: "The original plans were always that the regeneration of Sighthill required all the high rises to be demolished.
"That was reversed, but the circumstances have changed completely now.
"At that time we were looking at being able to invest in Sighthill in 10 or 20 years, but then the opportunity of the Youth Olympic Games bid came along.
"What was on offer is completely different to what is being offered now.
"It's real, it's happening, the money's there.
"I'm sensitive to the fact change is difficult, but this is change that is demonstrably for the good."
The land on which Sighthill was built in 1964 used to be farmland, with a railway line passing through it between Buchanan St Railway Station to St Rollox Works and the site of Pinkston Power Station at Port Dundas, which provided power for the city's tram network.
The building work on the new homes was completed in 1969.
After it went through its many changes, new landlord Glasgow Housing Association stopped letting flats in Fountainwell in 2005 as it mulled over whether to demolish the flats.
The first demolitions took place in July 13, 2008 when Eagle Heights and Barony Heights were pulled down.
Tennant Heights, Phoenix Heights and St Rollox Heights followed on November 29, 2009.