Gaddafi's son Saif al-Arab was well known to German police
Saif al-Arab Gaddafi, who died in a Nato air strike in Libya on Saturday, was often in trouble while studying in Germany
The second youngest of Gaddafi's sons was also the most obscure, but if Saif al-Arab (the name means Sword of the Arabs) was something of an enigma in diplomatic circles he was becomingly increasingly well known to the police in Munich, where he was a student at the city's Technical University from 2006.
Earlier this year, German prosecutors dropped an investigation into allegations of arms smuggling against him. Der Spiegel reported that the police believed they had solid evidence that Saif (not to be confused with his more prominent older brother Saif al-Islam) had organised the transport of a bag containing an assault rifle, a revolver and ammunition from Munich to Paris in 2007.
Police officers told the magazine the prosecution was abandoned for political reasons and because of the fear that the Tripoli regime would retaliate against German businesses and residents. Prosecutors denied the allegation of political interference.
In another incident in 2006, Saif was detained after a fight with a Munich nightclub bouncer. The brawl broke out, according to a press account, after his girlfriend began stripping on the dancefloor.
Saif was reported in Der Spiegel to be under investigation for subsequently ordering an acid attack on the bouncer. The Libyan embassy tried to win him legal immunity by having him accredited as a diplomat but the request was turned down.
In 2008, the police were called to deal with another complaint against Saif when neighbours alleged that his Ferrari exhaust made too much noise. The car was impounded.
When the Libyan revolt broke out, his father called him home, put him charge of a unit of loyalist troops and sent him to the east. It is not clear how much combat he was involved in, nor what his role was in attacks on civilians.
When the UN security council imposed sanctions on the Gaddafi regime in February, Saif was the subject of a travel ban, but not an asset freeze like most of his brothers.
This was not the first time he was reported hit by a western air strike. In 1986, the four year-old Saif was said to have been injured by the US bombing of another of his father's residences. On that occasion the attack was ordered by Ronald Reagan in retaliation for the suspected Libyan role in the bombing of a Berlin discotheque.