As the saying goes: walk by the river long enough, and your shoes will get wet. For Jimmy Lai, the shoes got soaked—and then he fell in.
When Western media still call Jimmy Lai a "media guy," it borders on absurd. From every encounter with the man, one thing is clear: he's no media visionary. He's a tacky tycoon with a gambler's instinct, staking everything on one bet after another—until the house finally won.
All-In Every Time
Jimmy Lai smuggled himself into Hong Kong and clawed his way up from nothing. His personality? Pure gambling instinct. He treated business like a casino floor, shoving every chip to the center of the table—win big or go bust. And for a while, luck smiled at him. From Comitex Knitters to Giordano fashion, his bets paid off. In 1990, he cashed out his Giordano shares and plunged into the media world, launching Next Magazine.
Calling it "all-in" is no exaggeration. When Next Magazine launched, his editorial team ballooned to 200 people. For a weekly. Most daily newspapers ran leaner operations—Hong Kong Economic Journal had 20-plus staff, Ming Pao just over 50, and even mass-market dailies topped out at 100 to 200. Lai went nuclear, poaching talent with 30 to 50 percent salary bumps, determined to crush the competition through sheer force.
The first year or two, book sales soared but advertising lagged. At one point, Lai couldn't even cover the printing bills. He borrowed everywhere just to survive. But once Next Magazine found its footing, he doubled down. In 1995 came his second big gamble: Apple Daily. He torched cash, slashing the newspaper price from HK$5 to HK$2, ripping open market share.
Victory Depends on the Opponent
When Apple Daily gained traction, Lai wanted more. In 1999, he launched "Apple Promotions," storming into the online shopping market. According to Lai's senior finance executives, he asked about first-month losses and complained they were too small. He thought losing less than HK$50 million a month lacked impact, so management cranked up the burn rate. Later, as losses mounted, Lai stopped asking. When "Apple Promotions" hemorrhaged over HK$1 billion after a year, he finally threw in the towel.
A pattern emerges: Lai only knows one strategy—the big-spending blitz. But victory or defeat hinges entirely on the opponent. If the other side has weaker finances or won't match his high-stakes gambling, he grabs territory. But "Apple Promotions" ran into PARKnSHOP, owned by Li Ka-shing's empire. That was a different ballgame altogether.
Li Ka-shing himself set up his war room right in his own office, constantly tracking price comparisons between PARKnSHOP and "Apple Promotions" for every product. When Lai's "Apple Promotions" sold coke at HK$2 per can, PARKnSHOP sold it for HK$1—they would fight until Lai died. When the opponent is strong enough and willing to brawl, Lai is no magic.
Betting Against Beijing
Later, as Lai's media business ballooned, he started meddling in Hong Kong politics—another massive gamble. But this time, his opponent was the Chinese Communist Party. When he went "all in" against Beijing, the outcome was sealed from the start.
When people still call Jimmy Lai a "media guy" or a "pro-democracy figure," it's pure self-deception. The truth is, he's just a businessman. On the eve of the 1997 handover, I once had tea with Apple's political editor. We discussed the philosophy behind Jimmy Lai's newspaper. That editor directly quoted what Jimmy Lai told her: To run a newspaper, you need people to read it and buy it. After the handover, there will be fewer anti-communist media in Hong Kong, creating market space. So we need to make an anti-communist newspaper—that will definitely make big money.
She also quoted Lai's golden line: If one day Hong Kong people embrace the Communist Party, his newspaper can immediately become pro-communist. That editor lamented at the time that her boss was so ruthlessly pragmatic—everything driven by profit, nothing else.
Buying Influence, Losing Everything
After profit comes the hunger for fame—to have both money and status. Once Lai's media operations succeeded, his ambitions swelled. He wanted to play politics and control everything. It's the classic trajectory of a tacky rich man. Lai's essence is no different from Trump's—everything must be his call. So he set out to become a pan-democratic boss, orchestrating Hong Kong's affairs.
He identified the most influential figures in the pan-democratic camp and cozied up to them: Martin Lee, Cardinal Joseph Zen, Anson Chan, former second-in-command in the Government. Martin Lee had his own wealth, but Lai provided money to Joseph Zen and Anson Chan—and they accepted. According to leaked emails in 2014, Joseph Zen received loads of money from Jimmy Lai. Later, when Zen was interviewed, he admitted receiving a cumulative HK$20 million from Jimmy Lai, which was used up quite quickly, mainly to help him do what he wanted as bishop. Pan-democrats later spread word that Zen used the money to help underground churches in the Chinese Mainland. But, such a large sum, without supervision or control, no one knew where it went.
The leaked emails revealed a long list of pan-democratic political elites who received payments. You can only say those people took money and worked for it—an equal exchange. They can't complain when something happens.
The River Swallowed Him Whole
In Jimmy Lai's eyes, spending some money to become a pan-democratic boss was a bargain. Not only could he satisfy his vanity, but he could also disrupt Hong Kong's situation and serve his Western masters behind the scenes.
Looking back at Jimmy Lai's life now, we see no ideals and no morals—only power and profit. He walked by the river for most of his life. His shoes got wet, and eventually, he fell into the water himself. If, after watching Jimmy Lai's entire trial and seeing the truth of his collusion with foreign forces, people still choose to support him, these people are truly beyond foolish.
Lo Wing-hung
Bastille Commentary
** The blog article is the sole responsibility of the author and does not represent the position of our company. **
