BACK in the days before e-mail, Victor Li, the heir to Asia's largest family fortune, used to sleep with a fax machine by his bed, ready for his famously restless father, Li Ka-shing, to send through instructions at any time of night.

And on several occasions at meetings, before the elder Li walked into the room, young Victor asked - only half in jest - for the gathered executives to beg his dad to go easy on him, say sources who have worked with the Li family over many years.

The elder son of Li Ka-shing, a rags-to-riches property tycoon known as "Superman" in his adoptive Hong Kong, has always had big shoes to fill - and some members of the city's business and political elite now wonder if they will ever really fit.

Li Ka-shing, 84, anointed Victor, 48, as his successor at a shareholder meeting in May. Then in July, the elder son took up a two-thirds stake in the family trust, giving Victor control of a business empire valued by Forbes magazine at US$25.5 billion.

The group's assets span property, ports, power, water, supermarkets, drug stores and telecoms, and it has such a pervasive presence in Hong Kong that most of the city's 7 million people do business with it virtually every day. The group, led by flagship property developer Cheung Kong (Holdings) Ltd, spans 52 nations and employs 270,000 people.

Though an octogenarian, the elder Li is an active man outside of work, known to still play golf several times a week. He is active inside the Cheung Kong office tower as well. He is still the name and face of the company and continues to make the key business decisions, according to sources familiar with the group's inner workings.

Focused on the bottom line

But the day will come when Victor Li will be in charge.

For some, Victor is a numbers-focused manager, a master of detail who has a track record of running assets well - and a man who has had to deal with some immense personal challenges, including being kidnapped for ransom in his early 30s.

For others, he is too focused on the bottom line, lacking some of the people skills of his more outgoing and charismatic father, raising doubts over whether the next leader of the Li empire will be as adept at the wheeling and dealing that characterized his father's reign.

And for a few, he is a more complex character altogether, someone who, according to people who have worked with him, struggles to trust those around him - a trait not surprising for a man whose status as heir has made him a target for envy and greed from a very early age.

"He is a chip off the block - his father has passed to him everything that he knows about the business," said Simon Murray, chairman of commodities trading powerhouse Glencore International Plc, who has worked with the man he calls "K.S." as well as both sons.

"However, there is something else that his father has that Victor has to develop, the character of his father, which includes characteristics like humility, the ability to trust," adds Murray, who was formerly managing director of Li's ports-to-telecoms conglomerate, Hutchison Whampoa, and still sits on Cheung Kong's board.

Li Ka-shing and Victor both declined interview requests for this article, which is based on conversations with more than 20 people who have dealt with them.

A reserved and devoted family man who enjoys wind surfing, Victor Li has taken his children on hiking trips in Bavaria, Germany and peppers his conversation with comments about their progress, according to sources who know him.

"Victor is a very intelligent man," said Aron Harilela, son of the founder of Hong Kong's best-known Indian-owned business, Hotel Holdings. "He delegates a lot more than his father would, and the depth of information is a lot greater."

Harilela and Victor Li know each other from the Hong Kong General Chamber of Commerce, where Harilela recalls a discussion they once shared over landfills in Hong Kong. Victor Li rattled off data on trash disposal in the city. "He always has information that a lot of people don't have," Harilela said.

Victor, still in his early days as the family's controlling shareholder, was thrust into the spotlight on October 1 when a pleasure cruise for staff of one of the conglomerate's subsidiaries turned to disaster. It collided with a ferry and sank, killing 39 people, all from the company boat. Li Ka-shing and Victor rushed to the hospital where victims were sent, both men immediately pledging money to support the families that were struck by the tragedy.

Within the worlds of Hong Kong business and politics, however, a different portrait of Victor Li emerges.

One senior government source echoed comments made by some business sources who said he was too focused on the details and not enough on nurturing relationships. They draw a sharp contrast between father and son, who could hardly have been brought up in more different circumstances.

Survived kidnapping by gangster

Li Ka-shing was born in Chaozhou on the Chinese mainland and moved to Hong Kong when he was 12, quitting school when his family relocated. His father died three years later. Li Ka-shing went from a factory worker to launching a plastics business, the first step in his path to creating a business empire.

Victor grew up destined to be a billionaire, a Stanford University graduate groomed for decades as heir apparent. He is rarely seen in public without bodyguards, a legacy of his 1996 kidnapping by a Chinese gangster, Cheung Tze-keung, also known as "Big Spender."

According to media reports, he was seized at gunpoint between his office and home, handcuffed, blindfolded, held overnight and then released upon payment of a ransom. Li Ka-shing negotiated Victor's release face-to-face with Cheung, who wrapped himself in explosives as a threat to kill both of them, in case the billionaire had been followed by police, according to a March 2011 article that ran in the South China Morning Post.

The wife of another of Cheung's kidnap victims, Hong Kong tycoon Walter Kwok, said she understood Li paid a ransom of HK$1 billion (US$129 million) in cash. "Big Spender" was caught and executed in southern China in 1998.

Two decades later, Victor Li keeps his private life away from public view.

Victor's younger brother, Richard, 45, has a more relaxed demeanor than his elder sibling, preferring to wear open-neck shirts in contrast to the conservative suits of by his brother, who has spent 20 years in the family business. In announcing Victor Li as his formal successor in May, Li Ka-shing also pledged to continue to back Richard's ventures - a sign the younger son, who dropped out of Stanford University, has a special place in his father's heart.

Some sources, however, said Victor Li's quiet achievements were too easily overlooked by those outside the family business and that he had championed two of his father's most successful technology deals - large, early-stage investments in Facebook and Skype.

They said Victor Li also had more of a regional focus than his father, a perspective that should serve the group well as it extends beyond its stronghold in Hong Kong and the Chinese mainland and ventures deeper into property markets like Singapore.

"That is very much driven by Victor," said a source close to the family. "I think he is more strategic than his father. He is very risk conscious, about the need to manage risk, the need to mitigate risk."

Some sources say the real test for Victor Li will come when his "Superman" father is gone, especially in Hong Kong where Li Ka-shing's network of relationships may begin to suffer without him. "You find that with K.S., he is very long on memory, particularly those who have helped him. In that sense he is a very, very true friend," said a retired bureaucrat who has worked with the family. "I can't say the same of Victor."