Kim Jong Nam led a life of loneliness and fear and seclusion, rejected by his father, orphaned by his mother, stuck in a shadowy exile where he had to constantly worry about spies and secret agents and reporters.
And it all came to a pitiful end, with Kim slumped in a chair in a Malaysian airport clinic, his belly protruding from his navy blue polo shirt, then dying in an ambulance en route to the hospital. He had been smeared with VX, a lethal nerve agent that is used as a chemical weapon.
"He's like a country and western song - it's sad, sad stuff," said Michael Madden, editor of the North Korea Leadership Watch website.
Kim Jong Nam's painful demise is a blow for the United States and South Korea, which have lost a potential source of intelligence on the world's most secretive regime.
They have also lost a potential replacement for his half brother Kim Jong Un, the North Korean leader who has again thrown down the gauntlet to the outside world.
"Kim Jong Un is testing nukes and missiles like crazy," said Alexandre Mansourov, a North Korea leadership expert who once studied at Kim Il Sung University in Pyongyang. "Now he feels confident enough to send his goons around the world to assassinate people he doesn't like."
Kim Jong Un feels this emboldened because he keeps challenging the outside world, especially the United States, and it does nothing to stop him, Mansourov said. "It's a sign of supreme confidence that he can get away with anything, that he can literally get away with murder."
The blame for the well-planned attack on Kim Jong Nam in a Kuala Lumpur airport terminal on February 13 is, however, being directed squarely at the leader of North Korea.
Malaysia says that Kim Jong Nam died because of exposure to VX and has implicated eight North Koreans, including a diplomat and a scientist, in the attack.
South Korean intelligence officials have said that Kim Jong Un put out a "standing order" for his older half brother's assassination some years ago, but even so, analysts agree that he would have had to give the green light for this attack.
"The fact that so many North Korean agents were involved shows that the operation was planned well in advance and was done with Kim Jong Un's blessing," said Sue Mi Terry, a former North Korea analyst at the CIA.
It wouldn't be the first time Kim Jong Un has acted in such a ruthless way. The 33-year-old has ordered the purge or execution of several hundred officials during his five years at the helm. These included his uncle, Jang Song Thaek, who had been a mentor to Kim Jong Nam and was accused of amassing too much of his own power.
"This fits into the larger narrative of what Kim Jong Un wants to do," said Ken Gause, a North Korea leadership expert at CNA, a Virginia-based consulting firm. "He's getting rid of potential contenders to the throne."
Kim Jong Nam was the result of a secret relationship between North Korea's second generation leader Kim Jong Il and his consort, an actress named Sung Hye Rim.
He led a lonely childhood in Pyongyang, "without even one friend," Sung's sister wrote in her memoir.
When he was 8, he moved to Moscow with his aunt and grandmother, but hated it. He then moved on to Geneva. There, he seemed to fit in better, although he still lived in a cloud of half-truths.
"He introduced himself as the son of the North Korean ambassador," said Anthony Sahakian, a Swiss businessman who went to school with Kim Jong Nam, whom he knew as "Lee."
"North Korea, South Korea, we were 13 years old, we didn't know the difference."
But some things did make Kim Jong Nam different - he had, for instance, a driver's license that said he was older than he was.
"That was strange because he showed up in a Mercedes 600, driving it himself," Sahakian said, referring to the huge sedan that was a favourite among dictators. "At the time, all we wanted to do was drive, so we were very jealous. We'd skip class and go somewhere else during the day to drink coffee."
Kim Jong Nam was multilingual as a result of his international childhood. He spoke fluent English and French, and Sahakian said they conversed in Russian.
In 1988, when he was almost 18, Kim Jong Nam went back to Pyongyang and to a life of cloistered misery, the polar opposite from his freewheeling youth in Europe. To boot, he found that the affection his father had once showered upon him was now directed at a new family, which included a young boy called Jong Un.
Kim Jong Nam had talked about "life in the palace" being oppressive. "He had everything he could possibly desire, but he was in a black depression there," said a school friend who asked not to be named while discussing sensitive details.
So Kim Jong Il struck a deal with his son: If he got married and had a child, he could leave, the friend said.
Kim Jong Nam married and had a son in 1995, although it's not known exactly when he left North Korea.
Certainly, a turning point came in 2001, when the family was caught entering Japan on false Dominican Republic passports. Kim Jong Nam, whose passport name was Chinese for "Fat Bear," told the authorities that they wanted to go to Tokyo Disneyland.
After that, the family moved to Macau, where they were under Chinese protection and could live relatively freely, with Kim indulging his passion for gambling. He travelled to Beijing, where he was thought to have another family, and around southeast Asia, popping up in Jakarta, Indonesia, and Singapore.
He also travelled to Europe regularly, sometimes to see his oldest son, who had been studying in France, and sometimes on business, apparently buying wine or property for wealthy Asian clients.
He always kept his wits about him, said Sahakian, who had seen his old friend several times in Geneva in recent years. "He wasn't paranoid but he was worried," he said. "When he was out, he was careful and he avoided talking to Asians because he was worried they were spies. He was on his guard but it wouldn't stop him."
Although he had been mentioned as a potential leader in dynastic North Korea, friends say he did not have any interest in the prospect.
But he appears to have antagonised his younger brother just enough. In 2010, the day before Kim Jong Un was to make his first appearance as heir apparent in North Korea, Kim Jong Nam gave an interview to Japan's TV Asahi in which he said the choice was his father's and that there appeared to be internal reasons for hurrying the process along.
"Personally speaking, I am opposed to the third-generation succession," he said, a statement that might be considered anodyne elsewhere but was tantamount to treason in North Korea.
Madden, of North Korea Leadership Watch, said that there was always a chance of Kim Jong Nam's being thrust into the leadership. "Jong Nam still had a power base and there was always a remote possibility that he would take power," he said.
Terry, the former CIA analyst, agreed. "However improbable, there are always rumours that Kim Jong Nam could replace Kim Jong Un as the head of the regime at the behest of China or the US" she said.
There have been reports in South Korea that Kim Jong Nam had acted as a middleman between South Korean President Park Geun-hye and officials in North Korea. Just a couple of days before his death, a South Korean newspaper reported that Kim Jong Nam tried to defect to South Korea several years ago.
This would have given the regime ample reason to get rid of him, said Cheong Seong-chang, senior fellow at the Sejong Institute, a South Korean think tank.
Indeed, Kim Jong Nam's defection would have been much more catastrophic for the regime than that of Thae Yong-ho, the deputy North Korean ambassador in London who fled to South Korea last year, said one former official in the regime.
"Imagine how detrimental the impact would have been if Kim Jong Un's half brother were to speak out against Kim Jong Un," said the former official, asking not to be identified for his safety. "It would have a much bigger impact than Thae Yong-ho is having now in South Korea."
Thae has become an outspoken critic of the regime, calling for a flood of information into North Korea to encourage people there to flee or rise up.
The downside for the United States and South Korea is that they have lost the opportunity to recruit someone in the family to provide information. They have also lost someone who could be installed as a slightly friendlier leader in North Korea, while still maintaining the Kim family bloodline - an important factor in Korean culture.
"They wanted him alive, not dead," said Mansourov. "The only party interested in his premature departure was Pyongyang."