Eustace Hightower

In 56 AC, Eustace set sail with his brother Norman Hightower to escort Lady Elissa Farman, who was travelling under the false name Alys Hill in search of new lands. When the Iron Throne ordered her arrest and return to King's Landing in chains, the order reached Lord Donnel Hightower too late — the ships had already left Oldtown.

Twelve days out, the expedition ran into violent storms off the southwestern coast of Westeros. Some of the crew swore a kraken had swallowed Norman's ship, the Autumn Moon, during one of those storms.

Elissa's Sun Chaser guided the Lady Meredith to three uninhabited islets. There the two ships parted ways: Eustace turned back east toward home, while Elissa sailed on west into the unknown.

The journey back was no kinder: a leviathan tore open the Lady Meredith's hull at sea. Eustace tried to reach the Summer Isles but ended up landing in Sothoryos instead.

He spent a full year repairing his ship on that continent while his crew dwindled, some to sickness, others to disappearances no one could explain.

He hired Summer Islander sailors at high wages and sent the Lady Meredith on to Tall Trees Town. Nearly three years after leaving Oldtown, he sailed back into port, his ship sun-scorched but laden with valuable cargo.

In 59 AC, Eustace fell ill with the shivers and survived, but his wife and children did not. The same sickness also claimed his grandfather, Lord Donnel Hightower.

As Donnel's only surviving grandson, Eustace may have inherited the lordship of Oldtown, though the account leaves this as a possibility, not a confirmed fact.