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King Nanda Bayin's Siege of Ayutthaya, 1586–1587
In late 1586 King Nanda Bayin personally led a huge army to besiege Ayutthaya, hoping to crush the breakaway capital in a single campaign. Yet after a siege of about five months he still could not take it. This war gave rise to the story, famous among Thais, of the "sword in the teeth" assault on the Burmese camp, and it was when the Chandra Kasem Palace served as a command post.
The ≈ sign marks an approximate location. Borders on the map are modern and shown for orientation only. Campaign routes are approximate lines drawn from the chronicles and modern studies, not the exact path taken. Dashed lines are enemy armies.
The great army from Hanthawaddy
Accounts based on the Burmese chronicles say King Nanda Bayin set out on 19 October 1586 with two armies totalling about 25,000 men, 1,200 horses and 220 elephants. The Thai chronicles put the number of troops at around 250,000.
Both armies forced their way through the defences and reached Ayutthaya around December. Throughout this time the Crown Prince Mingyi Swa stayed behind to guard Hanthawaddy and did not join the campaign.
Defending the capital
The Thai side chose to hold out behind the walls of the capital, which was ringed by rivers. The Hanthawaddy army set up its siege camps to the north and east. The Chandra Kasem Palace (Wang Na, the Front Palace), Naresuan's residence, stood at the north-eastern corner of the city island, so it became the command post on the side where the enemy pressed hardest.
Camp raids and the sword in the teeth
Rather than risk a decisive battle in the open, Naresuan repeatedly led small bands of soldiers out to raid the enemy camps. On one occasion he killed Lak Wai Thammu, a Burmese commander who had come out to ambush him, with a thrust of his lance.
The chronicles also tell how he chased the enemy right up to King Nanda Bayin's royal camp, gripped his sword in his teeth and climbed the stockade. He was speared and fell back down, but still led his men back into the city. That sword became known as Phra Saeng Dap Khap Khai, "the sword held in the teeth to scale the camp". The original was lost when Ayutthaya fell in 1767, so King Rama I had a new one made.
The besiegers starve and retreat
The Burmese themselves record that the besieging army was not prepared for a long campaign. By February 1587 large numbers of soldiers had died from hunger and exposure to sun and rain, and in March supplies were still slipping into the city through gaps in the siege lines.
On 20 April 1587 the Hanthawaddy army began to withdraw. The Thais harried it the whole way, and only a small part of it made it back to Burmese territory. The Thai chronicles record the retreat in 1587.
Why this campaign matters
In this campaign King Nanda Bayin came in person to lead the siege of Ayutthaya; after it, he sent the Crown Prince to command in his place. The failure cost Hanthawaddy a great many men and made Naresuan's name feared.
Reading the route on the map
The line on the map shows only the general direction of the Hanthawaddy army's march from Hanthawaddy to Ayutthaya, because the sources used say only that it came in two armies, without naming the passes it took through the mountains. The position of King Nanda Bayin's royal camp, north of the city island, is also approximate.
Waypoints along the route
| Waypoint | Coordinates | Notes |
|---|---|---|
| 1. Hanthawaddy (Pegu) | 17.337, 96.480 | |
| 2. Ayutthaya | 14.348, 100.561 |
Where historians still disagree
- Army size: the Thai chronicles say about 250,000 men, while accounts based on the Burmese chronicles say about 25,000 — a tenfold difference.
- When the sword-in-the-teeth episode happened: most sources link it to the war of 1586–1587, but some articles describe it only broadly as happening during the wars after the declaration of independence, without giving a year.
- Where the enemy camps were: the sources used say only that the siege camps lay north and east of the capital, so marking a camp on a modern map is still an estimate.
Frequently asked questions
How long did King Nanda Bayin besiege Ayutthaya?
About five months, from around December 1586 until the retreat began on 20 April 1587, which corresponds to late BE 2129 into BE 2130 in the Thai calendar.
Where does the name of the 'sword in the teeth' come from?
The chronicles say that during the siege Naresuan gripped his sword in his teeth and climbed the stockade of King Nanda Bayin's royal camp. Even though he was speared and fell, he still led his men back, and the sword was named after the feat.
- Burmese–Siamese War (1584–1593) - Wikipedia
- Mingyi Swa - Wikipedia
- Learning Materials on the Life of King Naresuan the Great – Naresuan University (in Thai)
- Biography of King Naresuan the Great – TruePlookpanya (in Thai)
- The Phra Mala Biang Helmet and the Phra Saeng Dap Khap Khai Sword: From the Fall of Ayutthaya to the Rattanakosin Coronation – MGR Online (in Thai)
- “Phra Saeng Dap Khap Khai”: King Naresuan's Feat in the War against Nanda Bayin, 1586–1587 – Silpa Wattanatham (in Thai)
Last updated 10 November 2026