Trump was once a commanding figure in Atlantic City, the casino hub in America’s northeast, where his casinos accounted for nearly a third of gambling revenues in the early 1990s, according to The New York Times.

At the peak of his casino investment, Trump had four properties. But the real estate mogul ended up losing control of the casinos after a series of bankruptcies, the latest in 2009.

Last year he won a protracted legal tussle against a small company in Macau over the Trump trademark, with a local court authorising him to use his trademarks in hospitality, restaurants and similar businesses.

The timing of the latest move may add significance, given the potential for big changes in Macau’s casino industry in just a few years. The licences of Macau’s six casino operators begin to expire on March 31, 2020. It is still unclear whether the six will be allowed to continue operating in the city, and if new bidders will be allowed into the market.

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The revelation of his latest moves on his trademark sparks questions over Trump’s eventual intention of trying to grab a slice of the pie.

“It is a possibility, albeit remote,” gaming analyst Ben Lee, a managing partner at IGamiX Management and Consulting, said.

“His children constantly scout the globe looking for new businesses and to expand the Trump brand.

“Given that this trademark application comes a few years before the concession renewal between 2020 and 2022, one has to consider the possibility that he may look at applying for a new concession.”

Glenn McCartney, associate professor in international integrated resort management at the University of Macau, said the liberalisation of the city’s casino monopoly soon after the former Portugese enclave’s return to China had led to a bidding war.

In 2001, 21 investors from Macau, Hong Kong, the US, Malaysia, Australia, the UK, Taiwan and other places bid for three gaming concessions.

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The big winners after the liberalisation in February 2002 were casino tycoon Stanley Ho Hung-sun’s Sociedade de Jogos de Macau, a subsidiary of STDM, which had been the long-time holder of the monopoly; Galaxy Casino, owned by Hong Kong magnate Lui Che-woo; and Wynn Resorts, headed by American Steve Wynn.

“Globally everyone was trying to get into Macau,” McCartney said. “The coming renewal might be seen as a window of opportunity for those who couldn’t get it last time.” He said there had been speculation of a potential seventh operator in Macau.

The Wall Street Journal reported last year that Trump had bid for one of the three Macau casino licences in 2001 along with other investors including Macau billionaire Ng Lap-seng, who last month was convicted in the US of bribery and money laundering.

“A Trump partnership is a possibility, but to register trademarks is a common business practice,” McCartney said. “It does not mean that it will necessarily be materialised.” He said it might simply be a “defensive measure”, so no one can use the logo or brand in Macau.

In 2012, the Macau government accepted Trump’s request to register three brands: “Donald Trump”; “Trump Tower”; and “Trump International Hotel and Tower”.

But experts said it was too early to tell how supportive Beijing would be of a gaming project involving the current US president in Macau. “China did approve all his trademarks very quickly,” Lee said, referring to the mainland’s approval of 38 Trump trademarks in March, which included businesses ranging from hotels to golf resorts.