Alyn Velaryon’s raid on the Braavosi fleet was a striking naval victory that brought him fame but failed to achieve the strategic objective of securing the Stepstones. Defying the plan to wait at Tarth, he struck while the Braavosi command was gathered on Bloodstone. His ships inflicted heavy losses and returned with prisoners and captured stores, yet Racallio Ryndoon remained in power, and the attack left the Crown exposed to a conflict with Braavos.

Causes and competing plans

The Stepstones were already divided among rival powers when the royal expedition set out. Racallio Ryndoon still held Bloodstone, the largest island, and a few smaller rocks, although most of his ships had been swept from the sea. Pentoshi sellswords controlled the other islands, while Braavosi warships commanded the surrounding waters. The Tyroshi had nearly overwhelmed Racallio, but Lys and Myr made peace and attacked Tyrosh, forcing the Archon to recall his forces. Then the Sealord of Braavos, the Archon of Tyrosh, and Racallio formed a common cause, intending to rule the Stepstones jointly and restrict passage to ships licensed by Braavos or Tyrosh. Pentos, previously one of the powers in the islands, had been excluded from this arrangement.

King’s Hand Unwin Peake recognized that Westeros could not defeat Braavos in a sea war. His declared purpose was narrower: end Racallio’s pirate kingdom and establish a presence on Bloodstone so that the narrow sea could not again be closed. The royal fleet alone was too small for that task, so Peake ordered Alyn to bring the Velaryon ships and place them under Gedmund Peake’s command. Alyn assembled sixty war galleys, thirty longships, and more than a hundred cogs and great cogs to join the royal fleet. When Gedmund later sent Ned Bean to transfer command of the Velaryon squadrons to Alyn, Alyn refused the appointment. The delegation’s failure revealed the tension between the formal command arrangement and Alyn’s view that the fleet was his to lead.

The decision at Tarth

The combined fleet sailed south through the Gullet and was further enlarged off Tarth by a dozen longships commanded by Lord Bryndemere the Evenstar. The news he brought changed the expedition’s circumstances: the rival powers had combined, and passage through the Stepstones would be controlled by their licensing. Gedmund Peake, seasick during the voyage and nicknamed Gedmund Green-Sick by the sailors, chose to inform Peake of the new alliance. Because the Evenstar had already sent a raven to King’s Landing, Gedmund ordered the fleet to remain at Tarth until a reply arrived.

Alyn argued that waiting would cost the fleet its chance to surprise Racallio, but Gedmund would not change his decision. The commanders parted angrily. At dawn the next day, Ned Bean told Gedmund that Alyn and the entire Velaryon fleet had slipped away during the night. Gedmund assumed Alyn had retreated to Driftmark, and Bean called him a frightened boy. Both had misread the direction of the departure: Alyn had taken the fleet south toward the Stepstones, not north toward home.

The attack and naval victory

Three days later, while Gedmund and the royal fleet were still off Tarth awaiting a raven, Alyn’s attack began among the Stepstones’ rocks, sea stacks, and narrow waterways. The Braavosi were caught unprepared. Their grand admiral and forty captains were feasting on Bloodstone with Racallio and the Tyroshi envoys. Half the Braavosi ships were taken, burned, or sunk at anchor or alongside the docks; others were lost as they raised sail and tried to get underway.

The Braavosi dromond Grand Defiance escaped past several smaller Velaryon warships and reached open water, but Alyn himself was waiting there in Queen Rhaenys. The dromond was slow to turn and meet the attack. Queen Rhaenys struck its broadside under oar, and the collision split the Braavosi vessel nearly in two, smashing its oars, breaking through its hull, and bringing down its masts. When Alyn ordered his rowers to back away, water poured through the breach and Grand Defiance sank within moments. The loss of the great ship, which carried four hundred oars, made the defeat a conspicuous blow to the Braavosi fleet as well as a material one.

Spoils, acclaim, and the strategic cost

Alyn’s victory was complete at sea, though not without loss. Three Velaryon ships were lost, including True Heart, captained by Alyn’s cousin Daeron, who died when the ship sank. In return, Alyn sank more than thirty enemy ships and captured six galleys, eleven cogs, eighty-nine hostages, and large stores of food, drink, arms, and coin. Among the prizes was an elephant intended for the Sealord’s menagerie. The expedition brought these spoils back to Westeros, and Alyn acquired the name Oakenfist, which he carried for the rest of his long life.

His return turned the victory into a public spectacle. Sailing Queen Rhaenys up the Blackwater Rush, Alyn entered King’s Landing through the River Gate on the Sealord’s elephant. Tens of thousands lined the streets, cheering and clamoring to see the returning commander. Aegon III appeared to welcome him at the gates of the Red Keep. But the reception in the throne room was different: by the time Alyn arrived, the king had vanished, and Unwin Peake confronted him from the Iron Throne in anger.

Peake’s fury reflected the gap between the raid’s spectacular results and its failure to meet the Crown’s objective. Alyn had not captured Bloodstone or any other Stepstone, because the knights and men-at-arms needed to occupy the islands had remained aboard the royal fleet off Tarth. Racallio’s kingdom had not been destroyed; he appeared to have emerged stronger. The ships and spoils could not substitute for control of the islands, and the raid had given the Hand reason to fear war with Braavos, the richest and most powerful of the Nine Free Cities. The episode therefore leaves Alyn celebrated as a victorious admiral while showing how a bold tactical success could worsen the realm’s larger strategic position.