Do you think former British Prime Minister Tony Blair is embarrassed at the news footage now being regularly replayed on television around the world of him embracing Colonel Gaddafi during his visit to Tripoli in 2004?

Fleetingly, I think is the answer.

I suspect that Tony Blair is sufficiently certain in his world view not to suffer from too much self-recrimination or regret. And Donald Rumsfeld never seemed too distraught about the photographs of him shaking hands with Saddam Hussein.

But it does highlight the perils of doing deals – diplomatic and commercial – with autocracy. The Libyan strategy that Blair pursued was always high risk but with risk comes the opportunity for glory. Libya was a known sponsor of international terrorism, potentially a key energy supplier and situated bang on Europe’s doorstep.

Given its oil wealth and small population it was possible to foresee a post-Gaddafi Libya as a much more prosperous and stable Mediterranean neighbour. Blair’s ambition was to move Libya from pariah to partner through trade-backed diplomacy rather than military enforced regime change.

This required a policy of engagement and inducements rather than hostility and isolation. And for a while it looked quite good. Gaddafi renounced weapons of mass destruction, seemingly stopped backing other people’s terrorists and western companies won contracts. Meanwhile his son was being delicately wooed by the Euro-elite as a much more appealing eventual alternative to his father. But such a strategy requires some uncomfortable moments: prime ministerial visits, the Lockerbie deal and doing business with a regime intolerant of any internal dissent.

Now that Gaddafi’s rule has been challenged and he has unleashed such savage reprisals on his own people, this strategy of inducement is left exposed. It seems, at best, naïve and, at worst, as the hijacking of diplomacy by short-term commercial interests dazzled by Libya’s hydro-carbon riches.

But it might have worked. Had Saif al-Islam succeeded his father and lived up to the hopes that his now-sheepish friends in Europe and the US had for him, and if Libya had started the process of building the infrastructure of a civil society, then this policy would have been hailed a success.

Viewed then through a long lens, the moral hazards of doing business with the old Libya would have been regarded in the same way as those early discreet overtures to the IRA, as a practical if unsavoury necessity. Instead of being branded as venal opportunists, the commercial and diplomatic dealmakers would be hailed as pragmatic realists who had succeeded in bringing an old enemy in from the cold. And in immeasurably improving the living standards and prospects of the Libyan people.

Such distinctions rest on the fine edge of geopolitical unpredictability. Any policy of engagement with autocracy is always going to carry a mixture of motives, noble and otherwise. But as an alternative to war, coaxing reluctant dictators to exit stage left has much to recommend it.

The commercial deals that flow in the wake of these strategies – and flow they will in Burma, Sudan, Zimbabwe, maybe even Iran and North Korea one day – carry the attendant political risk of the strategy unravelling prematurely -as in Libya, with little warning and violently. The lesson of Libya is that these risks are never far from the surface, however stable things seem, and however much business seems to be in lockstep with broader political realignments.