By Katie Hunt
Business reporter, BBC News
Stanley Ho made his fortune from Macau's lucrative casino trade but the billionaire has struggled to adapt to the tiny territory's changing fortunes.
Mr Ho had a monopoly on gambling in Macau until 2002
Mr Ho's firm, Sociedade de Jogos de Macau (SJM), which had a monopoly on gambling for four decades until 2002, has lost out to slicker, foreign rivals who are attempting to transform Macau into Asia's Las Vegas.
SJM's share of gambling revenue in the former Portuguese territory, which surpassed the Las Vegas strip in 2006, declined to 40% in 2007 from 75% in 2005, a year after the first foreign company set up shop.
Mr Ho's famous old casino, the Lisboa, which is closely associated with Macau's seedy past of gangster gunfights, has proved less popular with punters than the glitzy casinos operated by US firms Las Vegas Sands, MGM Mirage and Wynn Resorts.
However, Mr Ho is fighting back. His firm plans to use the $494m (£247m) it raised from a stock exchange listing in neighbouring Hong Kong this month to give the Lisboa a long-awaited facelift and re-develop several other casinos in the territory.
Macau's gambling revenue has overtaken the Las Vegas strip's
The cramped, gaudy Lisboa, where women clad in revealing clothes vie to attract male customers, is in stark contrast to the slicker new venues that are trying to turn Macau into a family-friendly entertainment destination.
Whether investors like his plans will be clearer on Wednesday when SJM shares begin trading.
The listing and ambitious expansion plans marks a big push by Mr Ho, who turns 87 this year, to claw back the market share lost to his competitors - and to secure his legacy.
"Stanley Ho is swinging for the changes. He recognises his own mortality," said David Green, gaming practise director for Pricewaterhouse Coopers in Macau.
But the road to market has been dogged by controversies.
The company's shares were slated to begin trading last week but were delayed by a last-minute court challenge by Mr Ho's estranged sister Winnie, who questioned the legality of the share sale.
Some investors returned the shares they had bought because of the legal challenge, which was later quashed.
Ms Ho, who holds a stake in SJM's parent company, has filed more than 30 lawsuits against her brother in recent years.
The flotation has also been scaled back amid a weak stock market and delayed by queries from Hong Kong's stock market regulator about the shareholding structure of SJM's parent firm STDM - also controlled by Mr Ho.
The listing has also shed rare light on the workings of a secretive Chinese family empire, publicly revealing the 44 shareholders of SJM's parent company for the first time.
They include Mr Ho's third and fourth wives, three sisters in addition to Winnie Ho, and one of his 17 children - many of whom are also involved in Macau's gambling industry.
"It'll have to become more transparent because of continuous disclosure to the stock exchange," says Mr Green.
"They've already been lining up executives from overseas and there will be a different discipline in what they do."
Mr Ho has also been dogged by media reports of alleged associations with organised crime, repeatedly denied, that frustrated attempts to expand his empire in Canada and Australia.
His playboy life-style and the antics of his socialite children, that include film starlet Josie Ho, are mainstays of Hong Kong tabloids.
Some analysts say that the odds are stacked against Mr Ho and SJM, even though the stock market listing should enable the firm to compete better in the new Macau.
The industry faces a number of challenges.
One in five people in Macau work in a casino
Breakneck development in the territory has led to severe labour shortages.
The opening of five major new casinos in 2009 means that an additional 20,000 workers will be needed to staff them, says Gabriel Chan, an gaming industry analyst in Hong Kong with investment house Credit Suisse.
"Even a high-school dropout can get a job as a card dealer," says Mr Chan.
The credit crunch too has hit Macau, with plunging global stock markets hurting high-stakes gamblers.
What's more, Mr Chan says, many high-rollers come to Macau on trips organised by "junket operators". They offer credit to finance gambling but the cost and scarcity of credit is limiting the amount they can give.
New visa restrictions could also limit the number of mainland Chinese punters, who made up half of Macau's 27 million visitors in 2007.
The rules of the game have changed since Mr Ho's hey day, when the territory's dark, smoke-filled gambling dens were part of his cosy monopoly.
But the octogenarian is betting that the listing of his firm on the stock exchange will signal a turnaround in his fortunes.