POLLYANNA Chu Yuet Wah, 54, the Hong Kong billionaire buying Sincere Watch lock, stock and barrel for an undisclosed sum, must be experiencing some deja vu.

If the deal - which has not been finalised - goes through, it will not be the first time that Mrs Chu has come into ownership of a watch firm.

One of the cornerstones of the empire built by Mrs Chu and her husband, Nicholas Chu, was constructed from the remnants of another watch firm.

Golden Resorts - the Macau hotel and gambling business which Mrs Chu controls - used to make watches as a Hong Kong-listed firm called Medtech Group.

Before 2004, Mrs Chu's links to the watchmaker had been through an indirectly held stake of 0.5 per cent and her brother-in-law, Chu Yuk Kuen, who had also been Medtech's executive director.

Tenuous as those connections were, as the loss-making watch firm looked to diversify into Macau's gambling and hospitality scene in 2004, Mrs Chu and her father, Lee Wai Man, suddenly became A-listers because of the gaming business pedigree that they shared.

Company filings from Golden Resorts state that Mr Lee founded the Macau-based Gold Club gaming syndicate in 1990 and had been a 'casino consultant' for Caesars Palace in Las Vegas during the 1980s. Mrs Chu, the filings said, had also been involved in the development of her father's gaming business in Macau.

By early 2005, Mrs Chu had brokered a deal in which Medtech bought Macau's Grandview Hotel from a firm controlled by casino mogul Stanley Ho for HK$500 million (S$80.6 million). As part of the bargain, Medtech's chairman, Jenkin Cheung, who then owned 42.3 per cent of the firm, gave 1.2 billion shares in Medtech to a firm controlled by Mrs Chu as 'a gift'.

By the time the deal was sealed, Mrs Chu would come to own more than 11 per cent of the company before exercising the warrants that had been part of the deal, and Mr Cheung's share had been whittled down to almost 26 per cent.

From then on, the watchmaker's metamorphosis into a gaming and hospitality business grew as rapidly as Mrs Chu's involvement in the business itself. By April 2005, Mrs Chu became Medtech's managing director while her father was installed as a non-executive director.

Two weeks later, Medtech was renamed Golden Resorts Group and the following year, Medtech sold off its watch-related manufacturing business and trading business for a gain of about HK$6 million.

The same year, Mrs Chu's husband replaced Mr Cheung - who cited 'personal reasons' for his resignation - as chairman of Golden Resorts.

The couple would go on to forge the gaming half of their empire with their existing half - Kingston Capital Asia - whose businesses specialise in securities underwriting and placement services. In 2011, Kingston was injected into Golden Resorts and made the latter's subsidiary.

Based on numbers from June 30, 2010, the combination of the two firms drove Golden Resorts' net assets from HK$3.75 billion to HK$10.97 billion. By April 2011, Medtech would fade further from memory, as Golden Resorts officially became known as Kingston Financial Group on the Hong Kong Exchange.

As the same time, Mrs Chu's own name was pushed to the forefront, for the merger launched her into the Hong Kong Forbes 2012 list as the country's 32nd richest person with a net worth of US$1.23 billion.

From real estate to real money

Mrs Chu's trajectory of wealth finds its origins in an auspicious start in real estate during the go-go years of the 80s when she made her money in commercial property in the United States before returning to Hong Kong.

In Hong Kong, as she and her husband built their securities business, her trajectory had occasionally crossed the regulator's path.

In 1997, she was fined HK$10,000 by the Securities and Futures Commission (SFC) for acting as a commodities dealer's representative of Kingston Futures without being registered under the Commodities Trading Ordinance.

In 2003, Mrs Chu had to surrender her registrations under the ordinance on a 'non-admission basis' after the SFC accused her of accepting orders from two ex-staffers of Merrill Lynch (Asia Pacific) Ltd who were accused of manipulative trading in derivative warrants.

In 2009, Mrs Chu's name surfaced in Richard Li's high-profile bid to take telco firm PCCW private through a scheme that raised allegations of vote-buying.

While she was not named as a defendant in the resulting court proceedings, the SFC said that Mrs Chu, 'contrived a plot whereby employees of Golden Resorts, employees of Kingston ... would be induced to purchase one to three board lots of shares and then to sign proxy forms in favour of the scheme.'

While Mrs Chu denied the allegations, the judgment said that Mrs Chu was found to be among those that 'had engaged in the activity of arbitrageurs as described ... They did so to protect an investment made by them or by a client of them.' The scheme in question, however, was approved by the judge.

In the same year but on the European continent, Mrs Chu drew the attention of the football scene when she was linked to an £81 million (S$161 million) takeover bid of football club Birmingham City by barber-turned-tycoon Carson Yeung.

The Telegraph reported that Mr Yeung had arranged to borrow £57 million from Best China, which is owned by Mrs Chu, in order to close the Birmingham deal.

Even as Mrs Chu stands to come full circle with the selling and buying of a watch firm, Sincere Watch is completing a cycle of its own by going back to Hong Kong where it was once owned by Hong Kong retailer Peace Mark.