- Eyebrows were raised when the state-run People's Daily revealed that he is a member of the Communist Party -- something Ma has never fully commented on.
BEIJING: Jack Ma, the ebullient and unconventional billionaire founder of tech giant Alibaba and the totem of China's entrepreneurial brilliance, now finds himself up against a Communist leadership seemingly intent on hacking back his empire and issuing a lesson that no one is bigger than the party.
Ma, the most recognisable face in Asian business with a fortune estimated at around $58 billion, has already faced the ignominy of having the world's biggest-ever IPO spiked by Chinese regulators days before its launch.
The November share sale was set to see his wealth bulge to more than $70 billion in a record-breaking listing of the group's Ant Group financial arm in Hong Kong and Shanghai.
But Chinese regulators abruptly pulled the deal, over what initially appeared to be concerns about the company's reach into the finances of hundreds of millions of Chinese people.
It was a brutal public rebuke to Ma, who was then called in for dressing down by regulators and has since evaporated from the spotlight he normally so ably commands.
Now China's poster boy for enterprise finds himself again caught in the glare of the Communist-run state, with Thursday's announcement of an anti-monopoly probe into Alibaba, the tech giant he founded, and the summoning of Ant Group by regulators.
It is another public relations catastrophe for Ma, a Communist Party member, whose rags-to-riches backstory has come to embody a self-confident generation of Chinese entrepreneurs ready to shake up the world.
Charismatic, diminutive and fast-talking, Ma was cash-strapped and working as an English teacher when someone showed him the internet on a 1990s trip to the United States -- and he was hooked.
He toyed with several internet-related projects, before convincing a group of friends to give him $60,000 to start a new business in 1999 in China, then still emerging as an economic giant.
Alibaba was the result, an e-commerce empire founded from his bedroom in Hangzhou and which started an online shopping revolution and grew into a fintech titan.
The company changed the shopping habits of hundreds of millions of Chinese people, and catapulted Ma into the global limelight.
"The first time I used the internet, I touched on the keyboard and I find 'well, this is something I believe, it is something that is going to change the world and change China'," Ma once told CNN.
In 2014, Alibaba listed in New York in a world-record $25 billion offering.
Ant Group, in which Ma is the largest shareholder, is now the world-largest digital payments platform, claiming 731 million monthly users on the Alipay app.
But there are fears it reaches too deeply into the pockets of ordinary Chinese with its micro-loans, investment and insurance products.
Crossed the line?
Ma long enjoyed an image as the benevolent and unconventional billionaire. Sometimes referred to in China as "Father Ma", he is praised for his self-deprecation -- he recounts being rejected by Harvard "10 times" -- and a knack for lighting up company events with song-and-dance appearances as Lady Gaga, Snow White and Michael Jackson.
As his fortune grew, Ma rebranded as a philanthropist -- in 2019 retiring from the business to focus on giving.
But even his charitable work betrays an idiosyncratic touch.
After footage of a little boy in a village in central China who looked like Ma went viral, the businessman promised to pay for him to go through university.
But that reputation may be in the balance with the regulatory slap-down playing into a growing sense shared on China's Twitter-like Weibo that he has leaned into hubris by criticising fintech regulators.
He has faced his share of travails over the years in a country where getting rich risks catching the attention of the powerful.
Eyebrows were raised when the state-run People's Daily revealed that he is a member of the Communist Party -- something Ma has never fully commented on.
He had previously indicated that he preferred to keep the state at arm's length, telling the World Economic Forum in 2007: "My philosophy is to be in love with the government, but never marry them."
But perhaps the biggest challenges remain ahead, as the size and scale of his business mean that relationship may need to be renegotiated.