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Timeline: Year 2 of the Third Age (mostly)
Isildur returned to Gondor after Sauron was defeated in the War of the Last Alliance. As the heir of Elendil, Isildur was crowned as King of Arnor, becoming the lord of all the Dúnedain in the North and in the South. He stayed in Gondor for a year, restoring its order, but most of his army returned to Eriador.
Finally, Isildur felt that he could leave, and he was in haste, wanting to visit Imladris first. There were two reasons for this: his wife and youngest child Valandil waited for him there, and he also was in urgent need for the counsel of Elrond.
The route he decided to take was north from Osgiliath, up the Vales of Anduin and then to Imladris through a high pass in the mountains. It was a long way, but the only other possible route (west and then north) would have been even longer. In earlier days, the latter route would have been safer, but now that Sauron was defeated and the people of the Vales were his allies, Isildur thought that there was no difference. He also knew the land well.
He left from Osgiliath early in Ivanneth (September), 2 T.A. The journey to Imladris would take 40 days. Isildur’s three eldest sons – Elendur, Aratan and Ciryon – went with him. He had a guard of 200 men, but no horses fit for riding. Before he left, he declared his nephew Meneldil as King of Gondor, and it was said that Meneldil was actually well-pleased by Isildur’s departure.
Elendur was Isildur’s eldest son and his heir and dear to him. Elendur had accompanied his father throughout the war and was in Isildur’s full confidence. He knew that Isildur had the One Ring (he was probably one of the few who knew about it).
The first half of their journey was uneventful. On day 20, when they had come within sight of Greenwood in autumn colours, the rain and wind started and lasted for four days. They turned away from the banks of Anduin because of the resulting flood and went up to the slopes of the eastern side and took the ancient paths of the Silvan Elves that ran there near the forest border.
There’s a note about Woodland Elves in this chapter. Just like Isildur had only recently become King of Arnor after his father had fallen in the war, also Thranduil had about the same time become the King of the Silvan Elves. His army had returned to his woodland kingdom with the remnant of the Silvan army a year before Isildur’s march.
The day 30 of the journey was when the disaster happened. At that point, Isildur and his company were passing the north part of the Gladden Fields, a great marshland that had previously been a lake. Reed, rush and yellow iris as high as man grew there, and there were numerous islets. At the eastern side, there was a grassy path where men could walk, however. On their right, the forest loomed above them at the top of steep slopes, and on their left, there was the marsh and Anduin.
It was a fair day, and in the afternoon, Isildur’s men were in a good mood and singing, for they knew that the day’s march was soon ending, and that would mean that ¾ of their journey was done.
Suddenly, as the sun went into cloud, there was an Orc ambush from the forest. The Dúnedain were perhaps even 10 times outnumbered. This event is told a bit differently in the Silmarillion (in that version, the Orcs came from the Misty Mountains and attacked their camp). The Dúnedain formed a shield wall. Isildur had not expected such an attack and had a sense of foreboding for there was more cunning and design in the attack that should have been possible; it felt like Sauron’s revenge. He spoke to Elendur about this, and about the fact that there was no chance for outside help, for Thranduil’s army was four days away. Elendur reminded him of the priceless objects Isildur had with him. At this point, as the Orcs were drawing near, Isildur gives the shards of Narsil, Elendil’s broken sword, to his esquire Ohtar (meaning: warrior, soldier) and sends him away with a companion to save them.
The first part of the ambush ended in the seeming victory of the Dúnedain, and the rest of the Orcs withdrew to the Forest, and Isildur thought that they might have given up. The night was soon falling, and Isildur gave orders to continue the march towards the flat ground closer to the river.
These Orcs had been placed there by Sauron during the war with a mission to attack any Elven and Men’s forces that went through. They probably didn’t know that the War was over, and Sauron defeated, and they were eager to win Sauron’s praise (perhaps even more because they had let Thranduil’s army pass a year ago as the orcs had been outnumbered then). The Orcs didn’t know about the One Ring, but it was laden with Sauron’s will and called to all his servants for their aid. These were the reasons why the Orcs didn’t give up.
The Dúnedain had gone scarcely a mile when the Orcs attacked again with full force and closed into an unbroken ring around them, still silent and keeping their distance, but moving stealthily inwards in the darkness. Isildur had not more than 20 archers which he would have needed now. There was a pause; the situation looked grim.
At this point, Elendur went to his father who stood alone, lost in thought. Elendur asked Isildur if he could use the One Ring to command the Orcs to obey him, but Isildur told him that he can’t use the Ring because of the pain and because he doesn’t have the strength to bend it to his will. Isildur now knew that he had overestimated his own will against Sauron’s and admitted that “it should go to the Keepers of the Three”.
The main attack of the Orcs followed, and it was a hopeless situation. After some time, Elendur sought Isildur in the battlefield, bringing the grim news that Elendur’s two brothers were either dead or dying. Elendur asked – actually commanded – Isildur to flee with the One Ring and try to take it to the Keepers of the Three Elven Rings.
Isildur asked his son to forgive him, put the One Ring on his finger and vanished. He was wearing Elendilmir, which was a single white gem on his brow, but as Isildur put on the One Ring, the Elendilmir suddenly turned red and blazed like a burning star. Both Men and Orcs gave way in fear.
The battle ended in a horrible defeat, there was only one survivor among the Dúnedain, Elendur’s esquire who was stunned and found under the dead body of Elendur. This esquire was the main witness and the source of information about these events, for he had heard the discussions between Isildur and Elendur.
The text mentions that Elendur, who should have been a king afterwards, was one of the greatest and fairest of his kin and most like to his grandfather Elendil. Much later, Elrond noticed the great likeness to Elendur in Aragorn.
Isildur ran until he was sure that the Orcs didn’t pursue him. At midnight, he came to the banks of Anduin. He was weary and in despair. There he cast off his armour and weapons, and tried to reach the other shore by swimming, but the strong current pulled him downwards, towards the Gladden Fields. He had almost got across the stream when he found himself struggling with rushes and clinging weeds. Then suddenly he noticed the absence of the Ring. It was gone and he had no hope of finding it again. This feeling of loss was followed by an overwhelming desire to give up and stop struggling, but it soon passed, and now it felt like a great burden had gone away. The pain was gone. Isildur got to the other shore and out of the water. But there were Orcs, and they saw him as a terrifying shadow carrying a piercing eye like a star (Elendilmir), and they shot him, and he fell back into the water.
The text continues with naming the sources of the legend: Ohtar and his companion and the only survivor of the battle, Estelmo, being the main ones. There were also Woodmen rescuers who arrived quite soon after the battle. The details of Isildur’s death are pure surmise, but well-founded. We are told that this text is a historical document written only in the Fourth Age, when other evidence was discovered.
Of the new evidence, the most important objects were found in the restoration of Orthanc. Saruman had collected many jewels and heirlooms there, but in addition, they found a secret steel closet (Gimli’s help was needed to open it). In it, there was a small case of gold, attached to a fine chain. It was empty. Most probably, it had been where Isildur had kept the Ring. And beside it, there was Elendilmir: a white crystal upon a fillet of mithril. The question that is left unanswered is that these items must have been upon Isildur’s body, so had Saruman also found the remains of Isildur, and if so, what had he done with them?