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The youngest of three, Gregor was also the favorite of his father, who named him the Sword of Highhill after he beat his brother in an honor duel when they were both still young men. When Roslyn died, many expected Gregor to contest his brother's claim to the title, but Gregor was the first to kneel and it was Frederik who knighted him. Despite earning the nickname Gregor the Chillhearted for his vicousness in battle, Gregor loved his family, and like his father before him, married a noble Northern woman who bore him two sons. The first died after taking fever as a child, and his wife died in childbirth with the second, named Padraig. A second wife bore him a third son. While the third, Seth, barely survived childhood, Padraig was his pride and joy, a large boy who grew into a powerful specimen of the Steelhart bloodline. When a small fishing village near the Highhill was attacked, Lionel, Gregor's nephew and protege, ran to fight in an effort to impress his father, and Gregor rode after to protect the life of Frederik's heir. Lionel was killed in the thick of battle, and when Gregor carried his corpse home, a great storm had set the food storehouses on fire, and there were Steelhart men fighting Steelhart men at the tower. Injuring himself on a pitchfork after fighting to put out the flames, Gregor was heartbroken to find his brother had slain Padraig, and the Chillhearted succumbed to his wounds. When he woke, Frederik's wife was dead and the family was torn in half. While the Tragedy at Sanctum was exactly that, one House's hardships may be another's blessing, because it was what was needed for the Steelhart brothers to put their differences aside and show the Valardin House they can depend on the Dogs of War.

Sir Gregor's eyes are as cold as his nickname: the Chillhearted. Pale blue and blinking little, a burn scar marks features otherwise best described as plain, with dark black hair that catches some gray every now and then. Stubble can occasionally be found on his cheeks, but Gregor's features hold the fairness of his Northern mother, and he has aged considerably well despite a lifetime of battle. Towering over most men, Gregor doesn't surprise with Steelhart's broad shoulders and barrel chest. A straight nose and a grim line of a mouth complete this Steelhart man's features, and when he walks, he walks with a limp, but stubbornly is never found with a clutch or cane.

That static you feel when a storm is about to brew is not an uncommon feeling others get around Gregor. At rest, he holds a calm sobriety that can cause unease to those around him. When angry, Gregor bellows, but chooses his words carefully, equal parts discipline and rage. Gregor is a knight first and foremost, however, duty, honor, and loyalty is not only what he lives by, but what he expects from everyone in the Peerage.