The point was not lost on his media-savvy Hong Kong audience, who know that Mr Lai is not short of enemies who would be more than happy to shoot real arrows at him. But to others he is a hero, one of the few of the colony's mega-rich businessmen who is not afraid to say what he thinks of the incoming Chinese administration and has a Midas touch in identifying popular trends.
Before becoming a publisher he launched Giordano, one of Asia's most successful clothing chain stores. Like many of the businessmen who have made good in Hong Kong he arrived in the colony as a penniless illegal immigrant from China and got ahead by working day and night to scrape together enough money to start his own business.
He had the option of sitting tight and relishing in his fortune but when the tanks rolled into Tiananmen Square in 1989 to crush the Chinese democracy movement he was caught up in the mood of fear mingled with resistance which swept the colony. His shops were enrolled in the cause, dispensing pro-democracy T-shirts.
For most people in Hong Kong the outburst of emotion in 1989 was a passing phase, for Mr Lai it marked the start of his career as a publisher. He felt that Hong Kong's freedom was under threat, particularly the freedom of speech. The following year he launched a brash weekly news magazine called Next, mixing soft porn with hard politics and a lot more in between. Next was an instant success, not least because it was written in a style of vernacular Cantonese which this Cantonese-speaking population had never seen in print before.
Next is also a success because, like its owner, it seems not to be afraid of anything. The level of fear was put to the test two years ago when the magazine published a expose of the workings of one of the colony's most powerful triad gangs. Jimmy Lai's house was attacked and his magazine's offices ransacked. Other articles about triad gangs followed.
The following year Jimmy Lai came into confrontation with the Chinese government by publishing a column in which he described the Chinese Prime Minister, Li Peng, as a "turtle egg with a zero IQ". Mr Li is seen by many in Hong Kong, including Mr Lai, as primarily responsible for the Tiananmen massacre. Jimmy Lai now says he probably went too far, but characteristically said nothing of the kind when China reacted and his Giordano store in Peking was summarily closed down and a sequence of events set in motion obliging him to resign the chairmanship of the clothing company.
By then, however, his attention was elsewhere, focusing on a project for establishing the Apple Daily. Media specialists were rolled out to pronounce the project as "mad". But when the new paper was launched last year it astounded its critics by becoming another instant hit. Within months of publication Mr Lai was claiming to have secured market leadership, an astonishing feat.
The Chinese government, which has a very long and vindictive memory, banned Apple staff from receiving accreditation to cover official events. Then, Hong Kong's most vicious newspaper war broke out late last year. It was sparked by the Oriental Press Group, which has claimed market leadership for the past two decades. The prices of its papers were slashed, with other publishers reluctantly following suit.
It still rages without a truce in sight. Other publishers appear to be getting frantic. As for Jimmy Lai, he's off for a holiday in Brazil. This man is very cool. The television advert with the arrows says it all; they hit the spot but never draw blood.