Part 5: Tokugawa's Final Visit, 1941 – Prelude to invasion

TL;DR – Tokugawa’s Final Visit to Johor (and What It Reveals)

In early December 1941, Marquis Yoshichika Tokugawa returned to Malaya—this time in military uniform, as a key adviser to the Japanese 25th Army. Though not a soldier, he was viewed as the Emperor’s trusted emissary. His close friendship with Sultan Ibrahim of Johor proved critical: Johor became the launchpad for Japan’s final push into Singapore.

As Japanese generals moved into Istana Bukit Serene—converting its tower into a command post—Tokugawa walked a fine line between diplomacy, loyalty, and personal conviction. Meanwhile, the Sultan, declining evacuation, gambled his life on that friendship.

The rest is well-documented history: Singapore fell, the Sultan survived, and Tokugawa escaped trial—shielded, perhaps, by his imperial proximity. But who was Tokugawa really? A monarchist imperialist? A humanist scholar? A spy, a reformer, or both?

His story in the Fall of Singapore is largely unknown. But what hidden role did he also play in Tyersall's darkest hour. The events cast a long shadow over the story of Tyersall and Istana Woodneuk to this day. 

This final post in the Marquis Tokugawa series explores the contradictions, complexities, and quiet aftermath of a man who stood at the centre of Southeast Asia’s darkest chapter—and walked away.

Read on to uncover the full story.

Arrival

Tokugawa dressed in military uniform holding a traditional ceremonial sword

When the Japanese 25th Army launched its invasion of Malaya on 8 December 1941, General Tomoyuki Yamashita led the charge. At his side, though not in the chain of command, stood Marquis Yoshichika Tokugawa. As a scion of Japan’s most illustrious noble family, Tokugawa operated in a different sphere—one that placed him above most military and political machinations, and unsettlingly close to the emperor himself.

Tokugawa's official title was Adviser to the Japan Military Administration in Malai and Syonan—Malaya and Singapore. He also held a similar advisory role in the Philippines. It’s likely many in Yamashita’s senior command viewed him as the emperor’s representative—his eyes and ears on the ground.

His longstanding friendship with Sultan Ibrahim of Johor made him even more valuable. Johor was the strategic launchpad for Japan’s final assault on Singapore. What better advantage than a host who not only ruled the territory from which the attack would be staged, but who knew Singapore like the back of his hand and enjoyed the loyalty of the local Malay population?

For Sultan Ibrahim, the friendship was a lifeline. His concern would have been whether Tokugawa could keep the more hawkish Japanese officers at bay—men who might see the Sultan’s British connections as a liability. Known for his charm and shrewd political instincts, Sultan Ibrahim would have needed every iota of those qualities to survive the Japanese occupation.

When offered evacuation by the British, the Sultan declined. “Why should I run away from my home?” he asked—a courageous gamble explored in depth in Palace of Ghosts. This time, his instincts served him well.

Read the full story here

1942: Istana Bukit Serene, Johor Bahru

When Yamashita and his generals arrived in Johor Bahru, it was Tokugawa who escorted them to the gates of Istana Bukit Serene. Sultan Ibrahim greeted them with grace and warmth. After six weeks of brutal jungle warfare, the gleaming white Istana—completed just nine years earlier—must have been a alluring sight for the battle-weary soldiers. 

 

The Sultan, whose memory of his royal reception in Tokyo and an audience with the emperor was still fresh in his mind, was eager to return the honour. He hosted a grand reception for Tokugawa, Yamashita, and their officers, drawing on his reputation as one of the region’s most gracious hosts.

Istana Bukit Serene showing the palace tower later used as an observation post by Yamashita.

Istana Bukit Serene was a masterpiece of luxury and refinement, set atop a hill and surrounded by a large park it offered splendid views across the Straits of Johor to Singapore. Its five-story, 35-meter tower offered the best vantage point in the region—an ideal spot for Yamashita to oversee his final attack plans. Tokugawa, a previous visitor, would certainly have known this.

The Japanese generals were impressed. They decided to make the Istana their headquarters. The Sultan ceded the palace without protest—and continued to reside in it. For weeks, he lived side by side with the architects of Singapore’s invasion. His strategy of survival seemed to be working: he remained both alive and free.

The Fate of Tyersall

What followed—the swift invasion and harsh occupation of Singapore—is well documented. Less known is what became of Sultan Ibrahim and his Tyersall estate during the Japanese occupation. 

The conversations between Tokugawa and Sultan Ibrahim, or between him and General Yamashita, under the arched ceilings of Istana Bukit Serene may never be known? Nor the links between these and the events that led to the tradegy that befell Tyersal, changing it forever.  What we do know is what happened to the Tyersall estate: Chapter 11 of Palace of Ghosts, “Seven Hundred Ghosts,” reveals the shocking and untold story of the Tyersall estate's darkest days.

Learn more about Tyerasall and Istana Woodneuk during the war years

Tokugawa remained in Singapore throughout much of the occupation, but left before Japan’s surrender. While General Yamashita was later tried and executed for war crimes, Tokugawa was merely interrogated and never charged. His close relationship with the emperor may have spared him that fate. He died peacefully in 1976 at the age of 89.

Understanding Tokugawa

Despite their 20-year friendship, Sultan Ibrahim never fully understood Tokugawa—and he wasn’t alone. The Marquis defied simple categorization. He was a man of contradictions.

One narrative casts him as a privileged monarchist and imperial ideologue, collecting intelligence across Asia and enabling Japan’s expansionist agenda. In the 1930s, he was part of a network that undermined Japan’s fragile democracy, aligning himself with right-wing militarists. He was involved in two military coups (both of which failed) in 1931 and 1936.

A 1943 photograph Tokugawa seated in the centre of the front row of Japanese officials outside the Singapore Museum (from the collection of the National Museum of Singapore)

Yet another version of Tokugawa is that of a humanist: a patron of the arts, natural sciences, and education (for example founding the Tokugawa Art Museum); a philanthropist who donated much of his wealth to progressive causes; an important figure in the establishment of the Japan Socialist Party; and even an early conservationist. He evolved from a hunter of exotic animals to a member of Japan’s Society for the Protection of Birds and Animals.

E.J.H. Corner, Assistant Director of the Singapore Botanic Gardens during the occupation, worked under Tokugawa and later wrote The Marquis: A Tale of Syonan-to (1981). He described Tokugawa as a man shaped by the wisdom of his ancestor, Tokugawa Ieyasu, founder of the Tokugawa Shogunate. It was a flattering portrait—but one that sits uneasily with the contradictions of his life.

Indeed, Tokugawa’s journey—from a disinterested student to an academic, from ultranationalist to reformer, from imperial adviser to humanitarian—suggests a man continually transformed by his experiences. The Showa Reformation, the Malayan campaign, and Japan’s post-war humiliation may each have altered his worldview. Taken together, they might explain the chasm between his early and later selves.

The Marquis and The Sultan: A Fateful Friendship

What cannot be doubted is the closeness between Marquis Tokugawa and Sultan Ibrahim, or Tokugawa’s role as go-between for the Sultan and the Japanese military. In any communication chain, the messenger shapes the message. Both men were key links in a chain that connected all concerned. For some, given what followed, that chain might now seem ominous.

Sultan Ibrahim, 20 October 1945, from the Colonial Office archives

In the end, both men survived. Tokugawa resumed a quiet life in Japan. Sultan Ibrahim, investigated but cleared of collaboration, emerged to take part in the Japanese surrender ceremonies. He drove through the streets of Singapore with the Union Jack flying from his Rolls-Royce—along the very roads the Japanese had marched down just three years earlier.

The Marquis Tokugawa later in life. He passed away peacefully in 1976, aged 89. 

Singapore's Untold History

The story of Marquis Yoshichika Tokugawa is just one thread in a much larger, often-overlooked tapestry. Palace of Ghosts—subtitled Singapore’s Untold History—aims to shine a light on the hidden palaces and forgotten characters who shaped the destiny of the region. In doing so, it offers a deeper understanding of the past—and the complex, flawed, and fascinating individuals who lived it.

Find our more: read the book Palace of Ghosts