Little has been written in the Common Tongue about this strange and extraordinary adventurer, Racallio Ryndoon, but in the Free Cities his life has been the subject of two scholarly studies and uncounted numbers of songs, poems, and vulgar romances. In his native city, Tyrosh, his name remains anathema to men and women of good blood to this very day, whilst being revered by thieves, pirates, whores, drunkards, and their ilk.
Surprisingly little is known of his youth, and much of what we believe we know is false or contradictory. He was six-and-a-half feet tall, supposedly, with one shoulder higher than another, giving him a stooped posture and a rolling gait. He spoke a dozen dialects of Valyrian, suggesting that he was highborn, but he was infamously foul-mouthed too, suggesting that he came from the gutters. In the fashion of many Tyroshi, he was wont to dye his hair and beard. Purple was his favorite color (hinting at the possibility of a tie to Braavos), and most accounts of him make mention of long curling purple hair, oft streaked with orange. He liked sweet scents and would bathe in lavender or rosewater.
That he was a man of enormous ambition and enormous appetites seems clear. He was a glutton and a drunkard when at leisure, a demon when in battle. He could wield a sword with either hand, and sometimes fought with two at once. He honored the gods: all gods, everywhere. When battle threatened, he would throw the bones to choose which god to placate with a sacrifice. Though Tyrosh was a slave city, he hated slavery, suggesting that perhaps he himself had come from bondage. When wealthy (he gained and lost several fortures) he would buy any slave girl who caught his eye, kiss her, and set her free. He was open-handed with his men, claiming a share of plunder no greater than the least of them. In Tyrosh, he was known to toss gold coins to beggars. If a man admired something of his, be it a pair of boots, an emerald ring, or a wife, Racallio would press it on him as a gift.
He had a dozen wives and never beat them, but would sometimes command them to beat him. He loved kittens and hated cats. He loved pregnant women, but loathed children. From time to time he would dress in women’s clothes and play the whore, though his height and crooked back and purple beard made him more grotesque than female to the eye. Sometimes he would burst out laughing in the thick of battle. Sometimes he would sing bawdy songs instead.
Racallio Ryndoon was mad. Yet his men loved him, fought for him, died for him. And for a few short years, they made him a king.
In 133 AC, in the Stepstones, “Queen” Racallio was at the height of his power. Alyn Velaryon could perhaps have brought him down, but it would have cost him half his strength, he feared, and he would have need of every man if he were to have any hope of defeating the Red Kraken. He therefore chose talk instead of battle. Detaching his Lady Baela from the fleet, he sailed her into Bloodstone beneath a parley flag, to try to arrange free passage for his ships through Ryndoon’s waters.
Ultimately he succeeded, though Racallio kept him for more than a fortnight in his sprawling wooden fortress on Bloodstone. Whether Lord Alyn was a captive or a guest was never quite clear, even to his lordship himself, for his host was as changeable as the sea. One day he would hail Oakenfist as a friend and brother-in-arms, and urge him to join him in an attack on Tyrosh. The next he would throw the bones to see if he should put his guest to death. He insisted that Lord Alyn wrestle with him in a mud pit behind his fort, whilst hundreds of jeering pirates looked on. When he beheaded one of his own men accused of spying for the Tyroshi, Racallio presented Lord Alyn with the head as a token of their fellowship, but the very next day he accused his lordship of being in the Archon’s hire himself. To prove his innocence, Lord Alyn was forced to kill three Tyroshi prisoners. When he did, the “Queen” was so delighted with him that he sent two of his wives to Oakenfist’s bedchamber that night. “Give them sons,” Racallio commanded. “I want sons as brave and strong as you.” Our sources are at odds as to whether or not Lord Alyn did as he was bid.
In the end Ryndoon allowed that the Velaryon fleet might pass, for a price. He wanted three ships, an alliance writ on sheepskin and signed in blood, and a kiss. Oakenfist gave him the three least seaworthy ships in his fleet, an alliance writ on parchment and signed in maester’s ink, and the promise of a kiss from Lady Baela, should the “Queen” visit them on Driftmark. That proved sufficient. The fleet sailed through the Stepstones.
More trials awaited them, however. The next was Dorne. The Dornishmen were understandably alarmed with the sudden appearance of the large Velaryon fleet in the waters off Sunspear. Lacking any strength at sea themselves, however, they chose to regard Lord Alyn’s coming as a visit rather than an attack. Aliandra Martell, Princess of Dorne, came out to meet with him, accompanied by a dozen of her current favorites and suitors. The “new Nymeria” had just celebrated her eighteenth nameday, and was reportedly much taken with the young, handsome, dashing “Hero of the Stepstones,” the bold admiral who had humbled the Braavosi. Lord Alyn required fresh water and provisions for his ships, whilst Princess Aliandra required services of a more intimate nature. Bastard Born would have us believe that he provided them, Hard as Oak that he did not. We do know that the attentions the flirtatious Dornish princess lavished upon him much displeased her own lords, and angered her younger siblings, Qyle and Coryanne. Nonetheless, Lord Oakenfist got fresh casks of water, enough food to see them through to Oldtown and the Arbor, and charts showing the deadly whirlpools that lurked along the southern coast of Dorne.
Even so, it was in Dornish waters that Lord Velaryon suffered his first losses. A sudden storm blew up as the fleet was making its way past the drylands west of Salt Shore, scattering the ships and sinking two. Farther west, near the mouth of the Brimstone River, a damaged galley put in to take aboard fresh water and make certain repairs, and was attacked under the cover of darkness by bandits, who slaughtered her crew and looted her supplies.
Those losses were more than made good when Lord Oakenfist reached Oldtown, however. The great beacon atop the Hightower guided Lady Baela and the fleet up Whispering Sound to the harbor, where Lyonel Hightower himself came forth to meet them and welcome them to his city. The courtesy with which Lord Alyn treated Lady Sam warmed Lord Lyonel to him immediately, and the two youths struck up a fast friendship that did much to put all the old enmities between the blacks and greens to rest. Oldtown would provide twenty warships for the fleet, Hightower promised, and his good friend Lord Redwyne of the Arbor would send thirty. In a stroke, Lord Oakenfist’s fleet had become considerably more formidable.

The Velaryon fleet lingered overlong in Whispering Sound, waiting for Lord Redwyne and his promised galleys. Alyn Oakenfist enjoyed the hospitality of the Hightower, explored the ancient wynds and ways of Oldtown, and visited the Citadel, where he spent days poring over ancient charts and studying dusty Valyrian treatises about warship design and tactics for battle at sea. At the Starry Sept, he received the blessing of the High Septon, who traced a seven-pointed star upon his brow in holy oil, and sent him forth to bring down the Warrior’s wroth upon the ironmen and their Drowned God. Lord Velaryon was still at Oldtown when word of Queen Jaehaera’s death reached the city, followed within a few short days by the announcement of the king’s betrothal to Myrielle Peake. By that time, he had become close to Lady Sam as well as to Lord Lyonel, though whether he had any part in the writing of her infamous letter remains a matter of conjecture. It is known, however, that he dispatched letters to his own lady wife on Driftmark whilst at the Hightower. We do not know the contents.
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