This post contains minor spoilers for The Winds of Winter
“What sort of man was he? Honest and honorable, venal and grasping, proud?”
“Proud, for a certainty. Even arrogant. A faithful friend to Rhaegar, but prickly with others. Robert was his liege, but I’ve heard it said that Connington chafed at serving such a lord.” (TWOW, Arianne I)
Varys and Illyrio’s multiple conspiracies to strengthen the cause of the bright-black dragon was in ashes. The boy and the sellsword company surrounding him were floating west towards the Stormlands, leaving the schemes of Illyrio and Varys behind in Essos. Young Aegon, the “only dragon that the Golden Company needed”, was embarking on a dangerous course to land in Westeros with ten thousand sellswords but no dragons. Fortunately, aboard one of the ships bound for the shores of the Stormlands was an exiled knight and lord who would lead men in the wars to come and who had protected the young prince for many years.
Lord Jon Connington was everything Varys could have wished for: a fierce military commander, Hand of the King during Robert’s Rebellion and perhaps most importantly, a staunch and undying Targaryen loyalist.
The man who returned from exile, however, was a very different man from the one who had left Westeros nearly two decades ago. Defeat and humiliation had changed Connington from a strong lord who operated within the bounds of accepted Westerosi conduct into a man willing to do anything to put the boy onto the throne.
Jon Connington’s history up to Robert’s Rebellion reads like standard Westerosi fare. Ambitious and self-assured, Jon Connington was a squire alongside of Rhaegar Targaryen before possibly squiring for the Crown Prince himself. (Arianne believes that Connington was Rhaegar’s squire while Barristan lists Myles Mooton and Richard Lonmouth as Rhaegar’s squires) When his father died a few years before the start of Robert’s Rebellion, Jon became the Lord of Griffin’s Roost, one of the most powerful bannermen of his liege lord, Robert Baratheon. Connington’s upward mobility accelerated further when Robert’s Rebellion broke out.