In 2022, Raphael Wong and Figo Chan visited Jimmy Lai, a media mogul, at Hong Kong's Stanley prison, where he was being held pending trial on national security charges, two years after his arrest.

The three men had been involved in the mass demonstrations that swept Hong Kong in 2019, with hundreds of thousands of people marching to demand greater democratic freedoms and autonomy from China.

Outside of politics, they would frequently socialize over meals, sharing stories and jokes as they enjoyed a range of dishes, from traditional dim sum to Western-style pizza and claypot rice.

According to Chan, Jimmy Lai developed a taste for simple prison fare, including rice with pickled ginger, a preference that would have been hard to predict for a man known for his lavish lifestyle.

The reunion at the maximum-security prison was a stark contrast to their previous meetings, taking place amidst a backdrop of suppressed protests, jailed activists, and a transformed Hong Kong, where the once-boisterous streets were now subdued, and Jimmy Lai, formerly known as "Fatty Lai," had undergone a significant physical transformation, having lost a substantial amount of weight.

Despite their age difference, with Lai in his 70s and Wong and Chan roughly 40 years his junior, the three shared a vision for a alternative Hong Kong. As a prominent figure in the protests, Lai utilized his influential newspaper, Apple Daily, to advocate for a liberal democratic Hong Kong.

However, this endeavor became increasingly perilous following the implementation of a national security law by China's Communist Party in 2020, which imposed significant restrictions on the city.

Lai expressed a deep sense of gratitude towards Hong Kong, stating that he felt indebted to the city, despite holding UK citizenship, and chose not to leave.

In an interview with the BBC just hours before his arrest in 2020, Lai emotionally reflected on his connection to the city, saying, "I owe everything I have to this place… this is my way of giving back," as he struggled to hold back tears.

Lai's primary motivation was to preserve the freedoms that Hong Kong had afforded him, driving his unwavering support for the city's pro-democracy movement and his unrelenting criticism of the Communist Party, ultimately resulting in the loss of his own liberty.

The High Court's December ruling stated that Lai held a deep-seated animosity towards the Chinese Communist Party, driven by a desire to adopt Western values. This conviction was handed down after the court considered the evidence presented.

According to the court, Lai's goal was to see the party's leadership dismantled, with Xi Jinping's removal being a key objective. This was the underlying motivation behind his actions, as determined by the court.

Lai was found guilty on all charges, including sedition, which was brought under a colonial-era law. The charge of colluding with foreign forces carries a maximum penalty of life imprisonment, the most severe sentence among the charges he faced.

On 9 February, the court imposed a 20-year prison sentence on Lai in a hearing that lasted under 30 minutes. This sentence is the longest handed down to date under the NSL, with rights groups describing it as equivalent to a life sentence given Lai's age.

During his testimony, Lai denied the charge of collusion, stating that his actions were driven by a desire to uphold Hong Kong's core values, which he listed as the rule of law, freedom, democracy, freedom of speech, religion, and assembly.

Following his conviction in December, Hong Kong's chief executive, John Lee, expressed approval, stating that Lai had utilized his newspaper to instigate social unrest and promote violent behavior. Lee emphasized that the law does not permit anyone to compromise national interests under the pretense of advocating for human rights, democracy, and freedom.

In 2022, prior to Wong and Chan's release from prison, Lai requested that they join him in prayer, a gesture that caught Wong off guard.

During his time in solitary confinement, which was reportedly self-requested, Lai's Catholic faith became more profound. He devoted six hours daily to prayer and created drawings of Christ, sending them to friends through the mail. According to Wong, despite his hardships, Lai remained composed and fearless, exuding a sense of peace.

Throughout much of his life, Jimmy Lai had not sought a peaceful path. From fleeing China at the age of 12 to navigating the demanding factory environment and eventually building a media empire that challenged Beijing, Lai's journey was marked by perseverance and determination.

To Lai, Hong Kong represented a stark contrast to China – a hub of capitalism, opportunity, and freedom. After arriving in the then-British colony in 1959, he achieved success and subsequently found a platform to express his views, leveraging his media presence to shape public discourse.

Following its launch in 1995, Apple Daily quickly gained popularity and became a top-selling newspaper. Inspired by USA Today, the publication introduced a new approach to newspaper design and sparked a competitive pricing environment in the market.

The newspaper's content was diverse, featuring a range of topics from a guide to the "adult section" to in-depth investigative reports and columns written by economists and novelists. According to Francis Lee, a journalism professor at the Chinese University of Hong Kong, this broad approach was designed to cater to a wide audience.

Former staff members recall that Jimmy Lai encouraged them to take risks, adopting a "if you dared to do it, he would dare to let you do it" approach. However, they also mention that he had a temper and would often use strong language.

Lai is described by his former colleagues as an unconventional thinker and a forward-looking individual who was willing to experiment with new ideas. One editor noted that even before the iPhone's release, Lai predicted the importance of mobile phones, and his enthusiasm for innovation was relentless, with a constant stream of new ideas and proposals.

This willingness to challenge conventional practices was also evident during Lai's time in the clothing industry, according to Herbert Chow, a former marketing director at a competing brand. Chow observed that Lai was unafraid to disrupt the status quo and was willing to confront criticism and opposition in pursuit of his goals.

According to Chow, Jimmy Lai's circumstances were a direct result of his own actions, which ultimately led to the creation of Apple Daily, as well as his current situation.

A notable television advertisement for Apple Daily, which aired when Lai was 48, depicted him taking a bite of the forbidden fruit, surrounded by dozens of arrows targeting him.

This image would prove to be prophetic, as events unfolded in a manner that mirrored the scenario presented in the commercial.

Lai's introduction to chocolate as a child sparked his interest in Hong Kong, marking the beginning of a lifelong connection to the region.

As recounted in the 2007 documentary, The Call of the Entrepreneur, Lai's first experience with chocolate occurred when a passenger, after having their luggage carried at a Chinese railway station, gifted him a bar of chocolate and a tip, saying they were from Hong Kong, which Lai then idealized as a haven due to the unprecedented taste.

China under Mao Zedong's leadership was marked by a series of repressive initiatives, including rapid industrialization and the persecution of those deemed "class enemies". The Lai family, who had previously been engaged in business, found themselves targeted and blacklisted. Lai's father escaped to Hong Kong, while his mother was sentenced to a labor camp, leaving the family to face significant challenges.

In his later writings, Lai recalled the traumatic experiences of his childhood, including being forced to witness his mother's public humiliation. On one such occasion, he and his sisters were made to watch as their mother was subjected to taunts and physical abuse, an ordeal that left him feeling terrified and humiliated. Lai described the emotional toll of this event, stating that he was unable to move or speak, overwhelmed by shame and fear.

Despite the hardships they faced, Lai's grandmother remained a source of inspiration and encouragement. She would often conclude her stories with a message of resilience and determination, urging Lai to pursue a career in business, no matter how humble the venture might seem. Her words of wisdom had a lasting impact on Lai, shaping his aspirations and motivating him to succeed.

At the age of 12, Lai joined the millions of people who fled mainland China to escape the hardships and repression of Mao's rule. He made his way to Hong Kong, a journey that marked the beginning of a new chapter in his life. Like many others, Lai was driven by the hope of finding better opportunities and building a more secure future.

Upon his arrival in Hong Kong, Lai was hired by a factory that produced mittens, where he worked long hours but found a sense of purpose and belonging. It was during this period that he began to learn English, with the help of a coworker. This newfound skill would later serve him well, enabling him to communicate effectively in interviews and even testify in court with confidence and fluency.

At the age of 27, he had already gained significant experience in the textile industry, having managed a factory and invested successfully in the stock market, which enabled him to establish his own company, Comitex Knitters.

During his frequent business trips to New York, Lai was introduced to a book that would profoundly influence his perspective: The Road to Serfdom, written by Nobel laureate Friedrich Hayek, a prominent advocate of free-market capitalism. Lai took away the idea that the free exchange of information and spontaneous human reactions can lead to optimal outcomes, a concept he believed was embodied by Hong Kong.

This book sparked a lifelong passion for reading in Lai, who would often revisit the same texts multiple times and explore the entire oeuvre of authors he admired. As he explained in a 2009 interview, his goal was to thoroughly internalize the ideas he encountered, stating, "I want to turn the author's thoughts into my backyard garden. I want to buy a garden, not cut flowers."

After spending a decade in the manufacturing sector, Lai decided to pursue a new venture and founded the clothing chain Giordano in 1981, a company that would go on to become a pioneer in the fast-fashion industry. Giordano's success was so notable that Tadashi Yanai, the founder of Uniqlo, sought Lai's advice when expanding his Japanese label into new markets.

Lai expanded his business into China, which was undergoing significant changes following the death of Mao. As he noted in a 2007 documentary, he was enthusiastic about the prospects of China's transformation, stating that the country was poised to undergo a significant shift, similar to that of Western nations.

The 1989 crackdown on pro-democracy protests in Beijing's Tiananmen Square served as a stark reminder for Lai and the people of Hong Kong, which was slated to revert to Chinese control in 1997 pursuant to an agreement between China and the UK.

In a show of support, Giordano displayed pro-democracy banners in its Hong Kong stores and sold t-shirts featuring images of Tiananmen protest leaders, as well as anti-Beijing slogans.

In a display of solidarity with the student protesters in Beijing, approximately one million people took to the streets of Hong Kong, and until 2020, the city hosted the largest annual vigil to commemorate the Tiananmen Square massacre.

According to Lai, the events of 1989 marked a turning point for him, as he had previously been indifferent to China; however, the incident stirred something within him, evoking a sense of primal connection, much like a maternal call in the dead of night.

In the aftermath, Lai went on to launch a magazine called Next in the following year, and in 1994, he published a scathing open letter addressed to Li Peng, a key figure in the Tiananmen crackdown, referring to him as "the Butcher of Beijing" and making a disparaging remark about his intelligence.

A significant backlash ensued in Beijing. As a result, between 1994 and 1996, Giordano's main store in Beijing and 11 franchise locations in Shanghai ceased operations. Lai subsequently relinquished his shares and resigned from his position as chairman.

In a 2007 documentary, Lai expressed his motivations, stating, "Accumulating wealth alone holds little significance for me. However, by venturing into the media industry, I can provide people with information, which translates to choices and, ultimately, freedom."

According to Lee Wing Tat, a former Democratic Party lawmaker, Lai emerged as a key figure in Hong Kong's pro-democracy movement, engaging in strategic discussions with prominent leaders and demonstrating his active involvement.

Lai openly criticized the Chinese Communist Party, penning an essay in 1994 that read, "I am wholly opposed to the Communist Party due to its restriction of personal freedoms." Additionally, he began to express concerns about the impending transfer of Hong Kong's sovereignty from the United Kingdom to China, slated for 1997.

In his writings, Lai posed a poignant question, "As Hong Kongers prepares to return to the motherland after over a century of colonial rule, we take pride in this reunification. Yet, the question remains: should our loyalty to the motherland be unwavering, even if it comes at the cost of freedom?"

At the time of the handover, China's leader Jiang Zemin made a commitment that Hong Kong would be governed by its own people and would maintain a significant level of autonomy for a period of 50 years.

A pivotal moment for Lai came in 2014 with the outbreak of the Umbrella Movement, which was triggered by Beijing's decision not to permit fully democratic elections in Hong Kong.

For 79 days, protesters took over the city's central business areas, with Lai attending the site daily from 9am to 5pm, despite being targeted with animal entrails by an individual. According to former lawmaker Lee, Lai was present when the police began using tear gas, alongside a person known as Fatty.

The movement drew to a close after a court ruling led to the clearance of protest sites, but the government remained unmoved. It was not until five years later, in 2019, that Hong Kong was again plunged into turmoil, this time due to a proposed extradition bill that would have allowed suspects to be sent to mainland China.

Initial peaceful demonstrations in 2019 gradually escalated into violence, engulfing the city for six months. Protesters, clad in black, resorted to using bricks, Molotov cocktails, and other tactics, including storming the legislature and setting fires, while law enforcement responded with tear gas, rubber bullets, water cannons, and live ammunition.

Lai's involvement in the protests was notable, as he spent 20 months in custody for his participation in four unauthorized gatherings. A fellow protester expressed surprise at Lai's presence, describing him as a busy entrepreneur who nonetheless made an appearance.

The Apple Daily newspaper provided extensive coverage of the protests, which some critics viewed as a platform for anti-government sentiment.

According to government adviser Ronny Tong, Lai played a significant role in the protests by allowing Apple Daily to promote a slogan that Tong considered "completely false" – opposition to extradition to China – which resonated with individuals seeking to disrupt order in Hong Kong.

The question of whether Apple Daily contributed to sedition, and the extent of Lai's influence over the newspaper's stance, was a central issue in his 156-day national security trial.

Cheung Kim-hung, the former CEO of Next Digital, Apple Daily's parent company, and a witness who initially faced charges before cooperating with the prosecution, testified that Lai had directed the editorial team to encourage public demonstrations. Following the implementation of the National Security Law, the newspaper faced two raids and ultimately ceased operations in 2021.

Amidst the peak of the protests, Lai traveled to the United States, where he held a meeting with then-Vice President Mike Pence to discuss the developments in Hong Kong. Prior to the implementation of the National Security Law, Lai initiated a contentious campaign, despite facing internal opposition, which encouraged readers of Apple Daily to send letters to then-US President Donald Trump, appealing for his assistance in the Hong Kong situation.

The court ultimately determined that these actions constituted a public call for foreign intervention in Hong Kong's domestic affairs.

According to Tong, any notion that Hong Kong can undergo political reform without implicit approval from Beijing is unrealistic. Tong described the protests that took place in 2014 and 2019 as being contrary to logical reasoning.

The Chinese government asserts that Hong Kong has transitioned from a state of turmoil to one of governance and increased prosperity, thanks to the national security law and the establishment of a parliament comprised only of patriots. However, critics, including the hundreds of thousands of Hong Kong residents who have relocated, argue that dissent has been suppressed and the city's freedoms have been significantly restricted.

Lawmaker Lee is among those who have left, stating, "After arriving in the UK, I experienced nightmares and felt a deep sense of guilt. I couldn't help but wonder why I was able to live freely in another country, while many of my friends back home were imprisoned."

For years, Lai's family has been advocating for his freedom, expressing worries about his well-being due to his diabetes, but so far, these appeals have been unsuccessful. According to Lai's legal team in Hong Kong and the government, his medical requirements are being addressed.

Carmen Tsang, who is Lai's daughter-in-law and resides in Hong Kong with her family, mentioned that her children fondly remember their grandfather and the regular family gatherings he used to host every fortnight. Although his boisterous voice initially intimidated her daughter, the children enjoyed visiting him, perceiving him as an amusing person.

Carmen Tsang is uncertain whether Hong Kong, as it stands today, has a place for someone like Lai.

Lai made a remark, saying, "If there's a speck of dust in your eye, you just get rid of it, right?"