My latest piece for DIPLOMAT explores how Optimists, Pessimists and Cynics view options for helping a grotty dictatorship (say the dismal state of Sibya) move to something rather better.

Back in the mists of 2016, I shared with Diplomat readers my thoughts on bad leaders:

“Yes, we were wicked. But hey, look at the sheer scale of our wickedness. Be honest. Don’t you find that just a little bit …impressive?”

This appalling thought skews the psychology of whole populations. People who survive may quietly rejoice when the Bad Leader finally dies. But insofar as the Bad Leader left them a legacy of anything positive (new roads, factories and universities, perhaps a huge army with efficient weapons) it’s steeped in the blood of their own colleagues, friends and family members.

How do they look back on the Bad Leader’s reign of terror? Could they have done more to stop it, or at least reduce the harm? Did they turn away from the horror happening down the street, or down the corridor? Were they all, when it came to it, cowards who sold their souls to stay alive?

These grim existential questions emerge once the Bad Leader is dead, and has been Bad right to the end. What if well before that point the Bad Leader ponders the situation and starts to see advantage in being a Not-Quite-So-Bad Leader? And what if the rest of the world rather likes that idea and decides to help?

This brings us to one of the hardest thematic issues in diplomacy, the politics of ‘decompression’: helping a repressive regime make reforms towards something notably more pluralistic.

It turns out that there are three broad camps of international opinion:


Those prepared to push for ‘change’: the Gadflai clan must leave power so that Sibyans themselves at last have the chance to make a fresh democratic start.


Those who favour ‘stability’: Sibyans aren’t ready for democracy and never will be, plus rapid change can easily lead to conflict. Some Pessimists may have something to lose in Sibya (eg a strategic naval base or access to oil reserves), and so will push hard for the outcome that suits themselves.


Those (the great majority) who don’t care a jot about Sibya or Sibyans, but who do not want any new precedents for ‘humanitarian intervention’ or ‘regime change.’

Gadflai and his cronies are shrewd about all this. To head off any awkward UN votes against themselves, they’ll play the Optimists against the Pessimists and doff their caps to the Cynics.

What to do?

…  The problem with Gaddafi, sigh the Optimists, was that he just couldn’t let go. He shouted at us for betraying him when we politely hinted that he might think about stepping down! Bad Leaders really do seem to believe in their own eternal glory. Even if a Bad Leader can be persuaded to go, and a friendly country is willing to host them into their old age, is it an honourable use of taxpayers’ money quietly to bribe them and their odious elite to step down? They’ve stolen billions already!

Plus, sigh the Optimists even more sadly, can we credibly support Sibya moderates when there’s no justice on the programme? In a best-case scenario the villains who’ve brutalised them for decades stroll from their crimes and get re-legitimised by gushy Western op-eds praising those villains’ wisdom and dignity? Really?

The Pessimists and Cynics smirk at the Optimists grappling with these dilemmas. Why make life harder than it is already? Let’s be honest. There are no good options, or even principled options. Any so-called intervention will just make everything worse. Why not just work in good enough faith with Gadflai, and take things nice and slowly? Better the devil we all know. This is diplomacy.

And so to contrasting how Washington is treating North Korea and Iran:

President Trump is offering Kim Jong Un himself a superb deal based on trust: “If you work with us, be nice, loosen up and get rich, you can expect to stay in power for a loooong time. Why not win a Nobel Peace Prize along the way? Not bad!”

To Iran’s Supreme Leader Ali Khamenei he’s saying the exact opposite, based on distrust: “You’ve had your chance. You’ve blown it. Time to go. This time the US will not pussyfoot around. We’ll be there helping your internal enemies trample you into the dust. Sad!”

Optimists, Pessimists and Cynics alike are watching these rival approaches with more than keen interest.

As is the international business community where Iran is concerned – busily voting with its feet and its wallet?