Game of Thrones is a series built around plotting, deception, and mistrust. Devious characters like Varys, Petyr "Littlefinger" Baelish, and Tyrion Lannister constantly make clandestine power plays, manipulate those around them, and maneuver events to their own ends. The bloodiest betrayal is undoubtedly The Red Wedding. It's a seminal, jaw-dropping event that completely upsets the conventional narrative, with the duplicitous Freys slaughtering Robb Stark, his mother Catelyn, his pregnant wife Talisa, and much of his bannermen and army, aided by the ruthless Roose Bolton. Robb and Catelyn's deaths effectively bring the Northern rebellion to a catastrophic end. It is difficult to imagine any other betrayal having a more immediate and devastating impact on the story.
And yet, another double-cross is perhaps even more significant to the overall story and was a crucial factor in making the Red Wedding possible in the first place. Robb's childhood best friend is Theon Greyjoy, the ward of his father Ned Stark, and technically a hostage of House Stark after the Greyjoy Rebellion, which left Theon as the ostensible heir to the Iron Islands. Ned raised Theon alongside his own sons, and it was a fractious relationship. The Starks loved Theon, but he was also a political hostage, and if his father Balon attempted another revolt, Ned would have been expected to deal with him accordingly. This left Theon caught between two families, but this split loyalty becomes crucial when Robb needs someone he can trust.
After Ned Stark's death, Robb raises the Northern banners and marches south, with his supporters proclaiming him King in the North. Theon becomes one of Robb's closest advisers, trusted so implicitly that Robb sends him back to the Iron Islands to negotiate with Balon without hesitation. Robb believes that Theon can persuade his father to support Robb's claim. Instead, Theon sees an opportunity to prove himself to the family he has been waiting all of his life to impress.
Rather than returning to Robb, Theon joins the Greyjoy invasion of the North and spurns the family who actually raised him by capturing Winterfell, taking Bran and Rickon hostage in the process. This leads to Theon's apparent execution of the Stark boys and forces Robb to deal with another crisis far from the battlefield. It has two immediate consequences for Robb's campaign. Firstly, he loses one of his most trusted lieutenants and an effective scout and archer. More importantly, the capture of Winterfell creates another military problem that Robb cannot ignore. His forces are already stretched across the North and the Riverlands, and the need to respond to events at Winterfell further dilutes the war effort. When Ramsay Bolton descends on Winterfell, he wreaks havoc and makes the North even more unstable, paving the way for his father to stab Robb in the back, or rather, the front.
This betrayal leaves a lasting scar on Theon himself. Once Ramsay captures him, Theon spends much of the remaining story being tortured by what he did, and in a more literal sense of the word, by Ramsay. Theon remembers Robb not just as a former king, but as the brother who trusted him, and eventually thinks of the Starks as more of a family than his blood relatives. His guilt is particularly painful because Theon spends so much of his life defining himself as apart from the Starks, only to discover that the family he rejected was the only one who actually cared about him.
In George R. R. Martin's books, it's telling that despite the brutal tortures he endures at Ramsay's hands, Theon's thoughts so often return to his regret over abandoning the brother who chose him for the family who gave him up for dead:
"Robb... Robb who had been more a brother to Theon than any son born of Balon Greyjoy's loins. Murdered at the Red Wedding, butchered by the Freys. I should have been with him. Where was I? I should have died with him."
Theon's betrayal goes even further. His decision begins a chain reaction that ultimately dooms Robb and causes many tragedies. If Theon doesn't betray Robb, then he has no reason to seize Winterfell. If Winterfell isn't taken, then Robb doesn't have to contend with Bran and Rickon's apparent deaths, which leads to him marrying Talisa/Jeyne Westerling and reneging on his agreement with the Freys. That, in turn, drives Walder Frey toward revenge, allowing Tywin Lannister and Roose Bolton to exploit the weaknesses in Robb's alliance. In short, there would be no shocking episode like the Red Wedding if Theon stayed with Robb.
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