When CY Leung parachuted out of his insolvent property business to make his run for Hong Kong's top job, he tried to extract an additional £3 million from Australian firm UGL, emails obtained by Fairfax show.

In return for co-operating on the £77 million sale of DTZ, the real estate advisory empire he'd helped to build, Mr Leung wanted the Australians to not only underwrite £1.5 million in bonuses, and pay £4 million in business wealth that had been wiped out, but also to compensate him for £3 million that he'd sunk in the firm's loss-making franchise in Japan over the previous five years.

Audacious: Hong Kong Chief Executive Leung Chun-ying. Credit:Bloomberg

"It was like 'here's all my losing lottery tickets, could you buy them'," says one party to those negotiations in November 2011.

But it was not the audacity of Mr Leung's claim so much as the manner in which he made it that illuminates his political predicament today, as he battles mass pro-democracy protests across the city and widespread calls for him to resign as the city's Chief Executive.