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. **
The United States today is undeniably far less impressive than it was 40 years ago.
Back in 1983, when I was in college, a political science class focused specifically on the US government’s successful decision-making during the 1962 Cuban Missile Crisis. Harvard professor Graham Allison, later renowned for his theory of Thucydides Trap - The Rise of Great Powers, published a detailed article analyzing how the US managed to resolve this severe crisis so swiftly.
In 1962, at the height of the US-Soviet Cold War, the Soviets planned to deploy ballistic missiles in Cuba, right next to the US, in response to America’s missile deployments in Italy and Turkey. Then-President John F. Kennedy boldly imposed a naval blockade on Cuba, showing extraordinary courage and resolve. His actions ultimately forced the Soviets to withdraw their nuclear missiles. Allison praised the US decision-making in that episode as a model of democracy combined with high efficiency.
Those were truly America’s golden years. Kennedy became president at 43, successfully defused the Cuban Missile Crisis, but was assassinated just a year later at the age of 45. The prevailing US view then was that socialist regimes produced only aging leadership and could never match the youthful energy and efficiency of the capitalist system.
Time has marched on. The country once led by young leaders is now locked in the hands of elders. President Donald Trump is 79, older than Soviet leader Leonid Brezhnev when he died at 75—someone the US once criticized fiercely. Trump’s decision to launch a war against Iran is widely judged by scholars at home and abroad as a costly misstep.
Bloomberg reported on April 8 that Trump’s military action against the Iranian regime proved "a serious strategic failure." Rather than weakening rivals, it bolstered China and Russia, eroded America’s advantages, and ultimately positioned Iran as the strategic winner. The Islamic Revolutionary Guard Corps remains intact, Iran keeps control over the Strait of Hormuz, and the US "failed to achieve any military objectives."
The New York Times published a detailed feature on April 7 titled "How Trump Pulled the US Into a War With Iran." The report uncovers the inner workings of the decision and shows how, amid internal disagreements and repeated warnings, Trump ultimately chose war based largely on intuition. White House reporters Jonathan Swan and Maggie Haberman tracked this process closely. They highlight a pivotal moment on February 11, when Israeli Prime Minister Netanyahu visited the White House and aggressively pitched the plan to attack Iran in the White House Situation Room.
During a one-hour briefing, Netanyahu and Mossad chief David Barnea pressed Trump hard. They argued Iran was vulnerable to regime change and that a combined US-Israeli strike could topple the Islamic Republic. Netanyahu outlined what they saw as near-certain conditions for victory, including:
1. Destroying Iran’s ballistic missile program within weeks;
2. Weakening the Iranian regime enough to prevent it from blockading the Strait of Hormuz;
Third, the chance of Iran hitting US interests through neighboring countries was judged extremely low;
Fourth, street protests within Iran would flare again, and with Israeli intelligence agencies stirring things up, intense bombing could create an opening for Iranian opposition forces to topple the regime;
Fifth, Israel also suggested that Iranian Kurdish armed groups might cross from Iraq into Iran to open a ground front.
Trump responded at the time, saying, "Sounds good."
The day after the meeting—February 12—a briefing was held in the White House Situation Room with only US officials attending, who divided Netanyahu's proposals into four parts:
First, a decapitation strike—the assassination of Iran's Supreme Leader Khamenei;
Second, to weaken Iran's missile projection capabilities and its threats to neighboring countries;
Third, to spark large-scale protests among the Iranian people;
Fourth, regime change, with a secular leader taking control of Iran.
US officials judged that the first two objectives could be achieved through American intelligence and military power. However, the third and fourth goals promoted by Netanyahu—mass protests and regime change—are divorced from reality.
CIA Director Ratcliffe called the "fantasy of regime change" absurd and laughable. Secretary of State Rubio bluntly dismissed it as "complete nonsense." The top military leader, Joint Chiefs Chairman Caine, told Trump, "In my experience, this is basically Israel’s usual play—they tend to exaggerate, but their plans aren’t always flawless."
However, Trump remained interested in the first two objectives: a decapitation strike and weakening Iran's military strength.
In the days that followed, Joint Chiefs of Staff Chairman Caine presented Trump with a stark military assessment. He warned that a large-scale strike against Iran would severely deplete US weapons stockpiles, including interceptor missiles already strained by support for Israel and Ukraine. Caine also highlighted the risks of Iran blockading the Strait of Hormuz and the enormous challenges the US would face in securing the Gulf region.
Trump dismissed these warnings, convinced the Iranian regime would surrender before such consequences materialized. He was likely influenced by the previous year's US bombing of Iranian nuclear facilities, expecting this war to be just as brief.
Nevertheless, Trump was increasingly resolved to strike Iran. Meanwhile, peace talks between the US and Iran were still underway. The turning point came in late February, when new intelligence from US and Israeli agencies revealed that Iran’s supreme leader Khamenei and other senior officials would soon meet in a ground-level building. This would leave Khamenei fully exposed to an airstrike—an opportunity US and Israeli officials believed was fleeting and unlikely to recur.
On February 26, the White House Situation Room convened for a final discussion. Many expressed doubts about going to war, including Vice President Vance, who told Trump, “You know I think this is a bad idea, but if you want to do it, I’ll support you.” Joint Chiefs Chairman Caine withheld clear endorsement and focused on risk warnings. The strongest advocate was Defense Secretary Esper, who argued if the Iran issue is going to be resolved sooner or later, better to do it now. Ultimately, Trump made the strike decision impulsively, relying on his gut instinct.
The New York Times report exposes critical flaws in decision-making at the highest levels of the United States government. Although most advisors believed striking Iran was unwise, no one dared truly oppose Trump’s imperial-style leadership. Trump behaved like a stubborn, glory-seeking elder focused only on immediate gains—much like a retail investor chasing quick profits in the stock market. His choice dragged the US into a deep quagmire it still struggles to escape. Forty years ago, the US criticized socialist countries for flawed decision-making; today, those same issues have surfaced within America itself.
Lo Wing-hung
