One of the real weaknesses of despots and dictators is their methodology for the transition of power. One result of this is they very often die in office. Because their hold on the leadership role is inherently illegitimate, they find themselves throughout the history of their regimes beset on all sides by schemers, usurpers, disloyal advisers and plotting generals. They must spend a great deal of time and effort weakening and purging the threats to their continued power, and when the time comes there is very little in the way of genuinely loyal support for the transition to the despot’s chosen successor. All through history we see the passing of a powerful tyrant as the time when a nation, or indeed an empire, is most at risk, in terms of not only WHO might be pulling the levers of power, but also the very nature of that nation’s governance. A benign dictator can find his carefully selected successor overwhelmed by a brutal general, or a bright young techocrat who would set the country on a better path.

These are, as the imaginary Chinese curse and wholly manufactured proverb put it so well, interesting times. Kim Jong-il is 69 and in poor health. Hosni Mubarak is 82. Fidel Castro is 84. Robert Mugabe is 86. For that matter, Ali Khamenei is 71 and Ali al-Sistani just turned 80. All of these aged men have tremendous power and widespread cults of personality, and the impending end of their lives represents both significant risk and at least some real opportunity.

Egypt is an important, if less well discussed example. Upon the death of the elder Mubarak, it is likely that the nation will begin some reform of it’s political process, some relaxation of the state of emergency (in place since 1981) and movement towards democratization. To a large degree, the population of Egypt is more Islamic and more radicalized than the Mubarak regime has been, and any relaxation of the arbitrary power of the leadership could very likely lead to calls for ending the cooperative relationship with Israel, opening the Rafah crossing into Gaza and much more open and direct support for the Palestinian cause. One doesn’t have to have an especially colorful imagination to suspect that Israel and the United States’ response to this tilt of the axis might be cause for further conflict.

For that matter, Kim’s death has much less in the way of opportunity surrounding it. The “best case”, the collapse of the North Korean regime represents both a humanitarian and economic disaster for the Koreas, China, and to a lesser extent Japan and the US, with refugees streaming across the heavily mined DMZ in the south and the Chinese border in the north, with millions starving across vast swaths of Northeast Asia.. If it happens in mid-winter, the human cost could be immeasurable. Of course, the “worst case” is that, knowing he had only a short time to live, Kim launched an all out war to see his father’s vision of a Korea united under Pyongyang before his death. In between these two extremes are various scenarios of a highly militarized nuclear power careening rudderless as the various factions struggle for power in the vacuum left by Kim’s death and an undefined power transition process.

In Iran, Ayatollah Khameini is the source of Amedinajad’s power base and the enabler of the Revolutionary Guards increasing control over all aspects of Iranian politics and economy. His replacement, whether more in the Khomeini orginalist mold or from a more liberal point of view could bring about major changes and perhaps reignite the opposition movement, reduce the power of the military in the political process and enable the beginnings of real rapprochement with the west. In Zimbabwe, the end of the Mugabe era might well signal the re-opening of the country to international aid and support, with the attendant hopes for her battered economy and agricultural sector. In Cuba, Castro’s passing will likely be more symbolic than anything else, but will likely lead to fairly rapid re-integration with the US, including the end of the embargo and the beginning of some real investment.

In the next few years, the simple passage of time will accomplish what decades of secret wars, covert plots, attempted coups and assorted assassination attempts could not. Of course, when events happen at random, without warning, no one can control the outcome, and the truly important thing is how the rest of the world manages the fallout and controls expectations. Because in every case, we will certainly be surprised by the outcome.