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In Isildur's youth, Númenor's King Ar-Pharazôn was corrupted by Sauron, who urged the White Tree to be cut down. Isildur went to the courts of the king in disguise and stole a fruit of Nimloth, though the guards were alerted and he was severely wounded in his escape. He was badly wounded, but his sacrifice was not in vain; Nimloth was cut down and burned shortly afterwards, but the line of the White Tree continued.

The Silmarillion explains that Isildur, together with his father and brother, fled when Númenor was destroyed by Ilúvatar. Isildur and Anárion landed in the south and established the realm of Gondor, and their father landed in the north, founding the realm of Arnor.

Isildur settled on the east bank of the Anduin and established the city of Minas Ithil (which would later be named Minas Morgul), as well as the province of Ithilien and setting his throne alongside his brother Anárion in the city of Osgiliath. However, in 3429 (see the Appendix of The Return of the King, especially the chronology of the Second Age) Sauron captured Minas Ithil and destroyed the White Tree. Isildur and his family escaped down the Anduin by boat, bearing with them a seedling of the tree. They sailed to Lindon, seeking the Elven High King Gil-galad and his father in Arnor. Meanwhile, Anárion bought time for Gondor by defending Osgiliath and driving the Dark Lord back to the mountains, while Elendil and Gil-galad marshalled their forces.

He returned with his father and Gil-galad in the Last Alliance of Elves and Men in 3434. After the Alliance was victorious over Sauron's host at the Battle of Dagorlad, they advanced into Mordor and laid siege to Barad-dûr. With Minas Ithil recaptured, Isildur sent his younger sons Aratan and Ciryon to man that fortress, which would prevent Sauron and his forces from escaping that way. Isildur was accompanied throughout the war by his oldest son Elendur. The campaign in Mordor was long and bitter, and Anárion was slain by a stone from the Dark Tower.

After seven years of besieging the Dark Tower, the enemy was all but defeated and Sauron appeared to challenge the king. During the final battle on the slopes of Mount Doom, Elendil and Gil-galad were both slain in combat with the Dark Lord. Isildur took the hilt-shard of his father's sword Narsil, which had broken beneath Elendil when he fell, and cut the One Ring from Sauron's finger. This destroyed Sauron's physical form, but his malignant spirit later regenerated in his fortress in Mirkwood.

Despite the urging of Elrond and Círdan, Gil-galad's lieutenants, Isildur did not throw the Ring into the fires of Mount Doom; Instead, he claimed it as an heirloom for his House, and as weregild for the deaths of his father and brother.

After the fall of Sauron, the greater part of the army of Arnor returned home while Isildur stayed in Gondor for a year, restoring order and defining its boundaries. He planted the seedling of the White Tree in Minas Anor in memory of Anárion. As his brother's helm had been crushed during his death at Barad-dûr, Isildur left his helm from the overthrow of Sauron as the replacement for Gondor's crown. He placed Anárion's son Meneldil in charge of Gondor, and returned north to Arnor with his three sons. His wife and fourth son Valandil had stayed behind i throughout the War of the Last Alliance and the aftermath, and Isildur also sought further counsel from Elrond.

Isildur departed Minas Anor with a party of around 200 soldiers. His men had to march as they supposedly had around ten horses, mainly as beasts of burden and not for riding. They had two dozen archers who were armed with the deadly Númenórean steel bows but their numbers were too few to be effective.

Fatefully, he chose to travel the route along the Anduin, instead of the safer if longer North-South road. Sauron had deployed an army of Orcs East of the Misty Mountains, however, to attack any stragglers of the Last Alliance. The Orcs did not show themselves when the full armies of the Elves and Men passed by, but they were easily more than a match for a company.

Isildur was assailed at sunset, and though the first Orc sortie were beaten off, they regrouped and surrounded Isildur's party to prevent his escape. When nightfall came, the Orcs assaulted him from all sides.

The Dúnedain were surrounded and outnumbered, with Ciryon slain and Aratan mortally wounded in a failed attempt to rescue Elendur, who urged his father to flee. Isildur put on the Ring, hoping to escape under the cover of invisibility. Fleeing to the Anduin, he cast off his armour and tried to swim to the other side of the river, but the Ring slipped (of its own volition) from his finger. He was quickly overpowered by the Anduin's current, and so the Ring abandoned him. Isildur felt the Ring was missing and was compelled to give in to the river and drown, resigning his life at the loss of the Ring. Despite the darkness, the Elendilmir that he was wearing gave his position away to the Orcs on the far bank who were seeking survivors from the attack, and they killed him with their poisoned arrows. Isildur's squire, Ohtar, saved Narsil from the enemy, fleeing into the valley before the Orcs encircled Isildur's company. Estelmo, Elendur's squire, was found alive under his master's body, stunned by a club.

The Elves from Thranduil's kingdom quickly got word of the attack, although they were too late to save any of the Dúnedain. They organized a counter-attack, destroying the Orcs before they could mutilate the bodies of Isildur's company.

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