The arrest of Hong Kong media mogul Jimmy Lai Chee-ying and the police raid on the newsroom of his tabloid-style Apple Daily have turned the spotlight onto the tycoon’s business empire. Lai – one of the city’s most outspoken critics of Beijing – has reshaped Hong Kong’s media landscape through his company Next Digital, which has also grown influential in neighbouring Taiwan. He has also previously explored potential property investments in Myanmar through another of his companies. Next Digital, founded in Hong Kong in 1990, has faced growing pressure in recent years, bleeding revenue in the midst of a slower economic climate, while battling vocal threats and advertisement boycotts from pro-Beijing figures. Lai, along with his two sons and four Apple Daily staffers, was arrested on Monday over alleged violations of the sweeping national security law imposed by Beijing. The move sparked an outcry in Hong Kong and internationally as an unprecedented blow to press freedoms in the city, but was seen by Beijing as a necessary move against a high-profile figure accused of fomenting dissent. Lai’s media empire first expanded beyond Hong Kong when Next Digital entered the Taiwanese market with a sister publication of its gossipy Next Magazine in 2001, with a sold-out first edition featuring the ex-girlfriend of then-Taiwanese president Chen Shui-bian’s son-in-law. Despite controversy over the sensationalist reporting style, and two violent attacks on the Next offices, Lai launched the Taiwanese version of Apple Daily in 2003. Next Digital publications were soon among the bestselling in Taiwan’s boisterous media scene, shifting the landscape towards a more provocative reporting style and popularising paparazzi-style exposes of public figures. In the face of more organised ad boycotts in Hong Kong, Lai in 2007 said Next Media wanted its Taiwan operations to make up half its revenue in the following financial year, after suffering HK$200 million (US$25.8 million) in losses per year. But the company continued to suffer significant losses in Taiwan as well, including the rejection of a cable TV licence for Next-TV, launched in Taiwan in 2009. Media mogul Jimmy Lai freed on bail as activist calls her arrest ‘political suppression’ To cut his losses, Lai attempted to sell Next Media’s print and television assets in Taiwan for NT$17.5 billion (US$594.5 million) in 2012. But the bid fell through after tens of thousands protested against the sale to a group of investors which included the son of Want Want China Chairman Tsai Eng-meng, who owned the Beijing-leaning China Times . Financial challenges forced the media giant to sell a property in Taiwan to relieve financial burdens in 2018, and Next Magazine ended its operations in Taiwan in February this year. While Lai vowed to not sell his Next Media business in Taiwan in the wake of the failed deal, he has been selling property assets there, reportedly to sustain the media business. He was most recently found to have sold land in Taipei’s Da-An area, of around 31,400 square metres, to Taiwan-listed property developer Chong Hong, for NT$6.1 billion (US$207 million) through Chartwell Holding Ltd and Best Combo Ltd, both affiliated to Lai. My meeting with Paul Wolfowitz not sinister, says Jimmy Lai But Taiwan remains a key market for the media company. According to the company’s report from the 2019 financial year, Taiwan made up the largest audience of readers for Apple Daily with around 12 million monthly unique visitors, followed by 10.3 million in Hong Kong, 10 million in the United States and 285,000 in Canada. Next had 1,047 employees in Taiwan, compared to 1,275 in Hong Kong. As the media environment in Hong Kong has become more difficult in recent years, Next Media has suffered successive losses, with annual revenue dropping from HK$2.3 billion (US$296 million) in 2016 to HK$1.2 billion (US$154 million) in the latest financial year ending in March 2020. Apple Daily head Jimmy Lai donated millions to pan-democrats, leaked files show Lai’s business interests are reported to go beyond media investment. A set of leaked documents sent to major Hong Kong news outlets in July 2014 showed Lai was in talks over two developments in Myanmar’s commercial centre Yangon during multiple trips to the country in the previous year. According to the documents, Lai’s Hong Kong-registered company Best Combo was planning to build two towers in Yangon with local developer Shambhala Group, run by the established businessman Phone Win. The documents also showed Lai paid former US deputy defence secretary Paul Wolfowitz US$75,000 for “compensation for services in regards to Myanmar”. He was seen in photos with Wolfowitz , who was a senior member of the George W. Bush administration, on a visit to Myanmar in 2013 when they met high-level officials including president Thein Sein, armed forces commander-in-chief Senior General Min Aung Hlaing and other high-ranking members of the Tatmadaw, Myanmar’s military.