In a revealing radio interview, the former SNP minister said he was in favour of treating substance misuse as a health issue rather than a criminal one and said the war on drugs was “pointless”.
Mr MacAskill was taking part in Good Cop, Bad Cop, a BBC Radio Scotland programme, alongside former police officers Tom Wood and Peter Ritchie.
Asked his views on illegal drugs, Mr MacAskill said: “I think we should be moving towards dealing with it as a health problem.
“We face a significant problem. Drugs is Scotland is moving from Trainspotting 1 to Trainspotting 2 – it’s moving from cocaine and heroin to so-called legal highs.
“We have a Trainspotting generation who have been taking drugs for 25 years and whose bodies are wracked. It would be better to allow them to take drugs for their own safety rather than buy off the streets with the criminality involved.”
Asked if that was his view while in office, Mr MacAskill said: “Yes, I believed it in office. I’ve always thought the war on drugs is pointless and is harming. My experience in office confirmed it. I can think of senior police officers who thought exactly the same as me.
“What I thought to do was temper the position. I’m bound by party policy and by the wider desires of government. It wasn’t worth the fight – there were bigger fish to fry. As soon as I was out of office, I felt the ability to speak out about it.”
He was also asked about the issue of Police Scotland paying VAT. The national force spends around £20 million a year on the tax and is the only UK police force unable to reclaim it.
Mr MacAskill said he had been aware of the problem during the setting up of the force, but said the situation had been “foisted” on Holyrood by the Treasury.
Asked if he had foreseen the problem, he said: “Yes. Even with VAT being imposed there were still going to be considerable savings moving to a single service.
“But the second thing was there was an opportunity to try and engage with the UK government to try and work out a way, having moved from the local authority [policing model] how we could still find a way to avoid VAT.
“I can boil it down to this: We asked what we needed to do to avoid being liable for VAT; they said, ‘We’re not telling you’. The decision to foist VAT on the Scottish Government was a political decision by the Treasury.”
Mr MacAskill also denied suggestions from the former officers on the show that problems with Police Scotland were “serious and deep rooted” and said much of the criticism had been “shameful” and politically motivated.