Alyn is the twin brother of Cassana Connington, and the son and heir of Lord Orys Connington. He is next in line to the Lord Paramountcy of the Stormlands after the Conningtons usurped the Lord Paramountcy and Storm's End from House Baratheon during the Ascent of the Lion.
Alyn was born in 492 AC, along with his twin sister Cassana. He was the second of the twins to be born. Alyn's mother, a Tyrell from a cadet branch of the family, died giving birth to her children-- leaving the Connington twins in the sole care of their father, Orys, then Lord of Griffin's Roost.
Orys' heir had a relatively uneventful upbringing by the standards of Westerosi nobility. He spent most of his time with wetnurses, tutors and guardians, and saw his father only sparingly. On those rare occasions when he did see Lord Connington, the boy often found himself the subject of his notorious temper.
As Alyn grew, more and more of his time was spent on martial training and other perceived masculine pursuits such as hunting and riding, largely due to his father's influence. Having inherited his father's natural athletic ability, Alyn became a well versed rider, and his rigorous training regime would see him grow into a skilled warrior in his adolesence.
When Alyn was eight, his life changed forever after his father rebelled against House Baratheon and seized Storm's End, declaring himself Lord Paramount of the Stormlands and pledging his allegiance to the new King, Damon Lannister.
Though Alyn is a handsome and capable young man, many have formed negative opinions of him due to his haughty attitude and air of self-importance. He constantly yearns for his father's approval as the result of a childhood barren of any parental nurturing or attention, and has a view of the world and his position in it that some might refer to as abysmally naive.
The third era saw leave Storm's End and travel across Westeros, from the deserts of Dorne to the Wall. Plans of travel to Essos were abandoned after news of civil unrest there. Alyn returned to Storm's End after Orys Connington was chosen as Master of Coin, where he ruled in his father's stead under the influence of his advisors.
Alyn continued to rule Storm's End as his father served on the Small Council, attempting to fix lordly relationships between House Connington and their vassals.
Orys arranged a marriage between his son and Brynden Frey's sister.
Once Alysanne Rogers got wind of this plan, however, she formed a coalition with several other Storm lords (including Buckler, Penrose, Selmy and Staedmon), and pressured Orys, in the presence of the King and Queen, to get him to betrothe Alyn to Sybelle Swann, Orys' ward.
Alyn accompanied the Connington host that marched on Nightsong to reclaim it from the hands of Houses Ashford and Foote, and stormed the castle alongside his father's forces.
After helping to reclaim Nightsong, Alyn traveled to King's Landing in order to attend Queen Danae's Masquerade Ball.
Following an egregious trip to the capital, where Alyn embarrassed himself and his House before both the King and Queen, he was forcibly sent to Griffin's Roost by his father so that he could learn to become a better heir.
Alyn remained at Griffin's Roost under the watchful eye of Orys' cousin, Arthur Connington. He was made to perform menial tasks such as emptying chamber pots, shovelling horse shit and sharpening swords until Arthur deemed him humbled enough to begin learning the intricacies of lordship.
Alyn attended the Tourney at Blackhaven, where he distinguished himself in combat. His father and Lord Dondarrion discussed joining their houses by marrying Alyn to Corenna Dondarrion, despite his preexisting betrothal to Sybelle Swann.
Alyn advanced to the finals where he faced off against the heir to Blackhaven, Durran Dondarrion. Following the conclusion of the bout, in which Durran bested him, Alyn struck Blackhaven's heir in the back of the head with the pommel of his sword-- putting Durran into a coma which ultimately led to his death.
Fearing retribution from Lord Dondarrion, Orys spirited his son out of Blackhaven immediately and ordered him home to Storm's End. However, Alyn's party was ambushed on the road, and he was taken prisoner by Lord Daven Seaworth.
"Had he been that bold at twenty, or nine and ten, or however old [Alyn] Connington was?" - Thoughts of Damon Lannister
"He was a snivelling, pathetic mess. This was the fruit of his seed? A cowardly, upjumped, entitled, dishonest, pathetic little prick.
He couldn’t even take a punch." - Thoughts of Orys Connington
Orys Connington, Father
unnamed Tyrell, Mother
Cassana Connington, Sister
Alyce Connington, Aunt (deceased)