"... His killing in an air strike is militarily insignificant but diplomatically disastrous"

"... But his killing in an air strike is a grievous strategic error - militarily insignificant but diplomatically disastrous. The propaganda value of such unintended deaths is potentially severe”
Assassination of a head of state is illegal under international law, and forbidden by various US presidential orders. On the other hand, the targeted killing of those woven into the enemy chain of command is shrouded in legal ambiguity. Given the personalistic nature of the regime, and the "all means necessary" clause in UN Resolution 1973, it might be argued that killing Col Muammar Gaddafi and certain members of his family - such as his son Khamis, commander of an elite military brigade - would be permissible, even if it posed a risk to those non-combatants around the regime. Legality, though, indicates neither legitimacy nor prudence. This strike, and the death of Saif al-Arab, have produced little military result at the greatest diplomatic and symbolic cost to Nato...
In the 1991 Gulf War, a US stealth bomber directed two bombs at what was claimed to be a command-and-control bunker, but was in fact an Iraqi civilian shelter.
The result was 315 deaths, including 130 children. Col Gaddafi, like Saddam Hussein before him, will take every opportunity to exploit such errors to paint Western powers as indiscriminate aggressors.
Moreover, this is no longer a conventional war in which top-down direction is crucial. Pro-Gaddafi forces in both the besieged western city of Misrata and in the east have adapted to Nato's air power and are using increasingly unorthodox tactics.They need not rely on a stream of detailed orders from Tripoli, and can cause considerable harm to civilians without this guidance.
There is no doubt that, along with the military aim of disrupting command-and-control hubs, Nato sought a psychological effect, conscious of the possibility of "accidental assassination". The problem is that the direction of this effect is unclear. The dramatic visual impact of this air strike, and the death of those disconnected from political and military leadership, will harden the diplomatic opposition to the war, from Russia and China amongst others. more consequentially, it will anger the alliance's warier members, like Germany and Turkey, and inflame parts of Arab and African public opinion..."