Orwyle

The Conclave of Oldtown named Orwyle Grand Maester in 127 AC, after Mellos's death. Under his care, King Viserys I Targaryen recovered some of the health he had been losing for years.

When Viserys I died, Orwyle argued — by his own account, though other chronicles credit the stance to Lyman Beesbury — that the crown should go to Rhaenyra Targaryen. Beesbury's murder made him switch sides and swear loyalty to Aegon II.

He later travelled to Dragonstone himself, escorted by Ser Arryk Cargyll and Ser Gwayne Hightower, to negotiate with Rhaenyra on the king's behalf. She refused his terms, stripped him of his maester's chain — which passed to Gerardys — and had him thrown off the island.

When Prince Aemond Targaryen took command of the armies against Daemon Targaryen at Harrenhal, Orwyle urged him to seek aid from Storm's End; Aemond ignored him, as he ignored every other call for caution.

When Rhaenyra took King's Landing, the dowager queen Alicent Hightower ordered him to send ravens for help, but gold cloaks seized him before he could and locked him in the black cells. There, not knowing if he would live, he wrote his own account of the war.

Freed by Ser Perkin, Orwyle accompanied Queen Alicent and Lord Larys Strong to parley with Lord Borros Baratheon's army when it reached the waters of Blackwater Bay. With Aegon II restored to the throne, he remained Grand Maester until the king's death.

During the Hour of the Wolf, Lord Cregan Stark had him arrested for his part in that death: under torture he confessed to supplying the poison Larys Strong had used, though he insisted he had not known its purpose.

Sentenced to die, he followed Ser Perkin's example and asked to take the black; but before boarding ship for the Wall he bribed a guard and fled disguised as a beggar. He shaved his head and beard, took the name "Old Wyl," and went to work in a brothel on the Street of Silk, where he even taught some of the girls to read. One of them gave him away without meaning to, showing off her new skill to a City Watch sergeant.

The small council sentenced him to death, but the blind Lord Tyland Lannister, Hand of the King, argued he could not carry out the execution while the office of King's Justice stood vacant, and had him confined instead in a large, comfortable tower cell, with ink and parchment to keep writing.

He spent two years there, until the winter fever of 133 AC killed many of the city's maesters and Orwyle, by then an old man, was brought out to treat the sick.

When the fever took Lord Tyland too, the young King Aegon III ordered him to summon Lord Thaddeus Rowan to Goldengrove as the new Hand; Orwyle obeyed, perhaps hoping for a pardon that never came, and Lord Unwin Peake's men captured him and sent him back to his cell. Once a new King's Justice was finally named, he was executed as a traitor and deserter; for his age, birth, and long service, he was granted the mercy of dying by the sword.