For years, Adrian Cheng had all the trappings of a third-generation scion preparing to lead one of Hong Kong’s wealthiest clans into a new era. He infused his property projects with art, burnished Tsim Sha Tsui’s waterfront as a cultural district and invested in digital tokens.

This month, his heir-apparent status at the $26 billion family empire was thrown into doubt after his father Henry Cheng said the conglomerate is still looking for a successor.