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- "Stannis Baratheon is my king. Not to mention my friend. I do what he says and what he says alone."
- ―Ser Glendon to Grayson Mercer.
Ser Glendon Estermont is a major character in the fifth, sixth, seventh, and eighth seasons, and was previously a recurring character in the second and third seasons. He was a close friend of Stannis Baratheon and served as the captain of his personal guard, as well as one of his chief generals during the War of the Five Kings. Aside from his combat prowess, Glendon was known for being a skilled diplomat, and Stannis planned to name him Master of Laws on his Small Council once he claimed the Iron Throne.
Follwing Stannis' defeat at the Battle of the Blackwater, he sends Glendon to the Stormlands to rally the men sworn to the houses that had declared for Stannis to hold Storm's End in his name (as he was the rightful Lord of Storm's End following the death of his brother Renly.) This would lead him into conflict with Victarion Greyjoy, who was attempting to conquer the Stormlands in the name of his brother, Balon Greyjoy.
The conflict against Victarion's forces lead Glendon to try and secretly gain support from some of the lords of the Ashlands without Trevyr Blackgard's knowledge (as Trevyr had refused to support Stannis on several occasions.) Though this seemingly nearly came to fruition, Glendon was recalled by Stannis back the North as part of the march on Winterfell.
Glendon was one of Stannis' few generals that didn't desert him after he sacrificed his daughter Shireen to the Lord of Light. He seemingly perished during the Battle of Winterfell when Stannis' greatly depleted forces were routed by those of House Bolton, but he survived, badly wounded, and wandered the Wolfswood, half-delirious from his injuries, until he stumbled into Jon Snow's war camp, months after Stannis' defeat. His injuries were treated, and as repayment, he, like Davos Seaworth, decided to fight alongside Jon.
Sansa Stark, on the recommendation of Lord Petyr Baelish, places Ser Glendon in charge of a small force of Knights of the Vale and sends him to the Ashlands to try and shore up an alliance with House Blackgard, promising to support the Blackgards in their conflicts at home while the bulk of their army fought for Daenerys Targaryen, with the hopes that the Blackgards would do the same for them. This alliance never came to fruition, as the Black Day would occur before Glendon arrived at Ebonheart. Glendon would meet up with Sofina Blackgard and her loyalists and pledged to aid them in the war against King Althurin, promising to gain them support from House Stark.