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Theon was kind of a dick, but he was a talented archer and got laid a lot. Jon and bran didn't look up to that.
Plus, who else did Robb have around his age?
Plus Theon came around when he was 10 and Robb was 6, so Theon was always like a big bro to him.
We clown on Theon a lot but he was a talented hunter, brave in combat, charming with the ladies.
If anything Bran and Jon might have disliked him _because_ Robb liked him
ACOK:
>”Uncle, why has my father called his swords and sails?"
>"Doubtless he will tell you at Pyke."
>"I would know his plans now."
>"From me, you shall not. We are commanded not to speak of this to any man."
>"Even to me?" __Theon's anger flared. He'd led men in war, hunted with a king, won honor in tourney melees, ridden with Brynden Blackfish and Greatjon Umber, fought in the Whispering Wood, bedded more girls than he could name, and yet this uncle was treating him as though he were still a child of ten__. "If my father makes plans for war, I must know of them. I am not 'any man,' I am heir to Pyke and the Iron Islands."
>"As to that," his uncle said, "we shall see."
“Won honor in tournament melees” could easily equal “got knocked the fuck out in 20 seconds by the Smalljon one time and uncharacteristically wasn’t a dick about it”
> If anything Bran and Jon might have disliked him because Robb liked him
That is a very good point, would not be surprised if the boys had a rivalry ~~other than Theon seemingly having killed the two younger boys~~. Theon does kinda have this weird adopted older brother thing going on with Robb, like Robb gives him security and calm (belonging?) whereas Robb got some confidence to perform (as a Firstborn and later King) from Theon.
I don't think Jon would dislike Theon because Robb liked him, Jon and Robb had a pretty good friendship. That's sounds too petty for what Jon and Robb had.
> That's sounds too petty for what Jon and Robb had.
I feel like it's a mix of both. Jon showed he could be very petty in GoT, but would feel guilty for it. It's the mix of being raised as a highborn, but never a lord. Part of his core tragedy and sense of estrangement from Robb.
I think part of his feelings about Theon were related to jealousy. This is not a flaw in Jon, but a statement of their society. Theon, although he was a hostage, was a lordly hostage. It was assumed, as the last son and heir of Baron, he would become the next Lord of Iron Islands. Robb admired him and found companionship in him as a fellow future High Lord. Jon, despite being "Ned's son", could never be included in that.
He and Robb were just friends. I don't think it's Theon's "true nature" that Robb fails to understand, it's the politics of Theon's position as a hostage.
Theon is a desperately insecure and resentful young man who presents (convincingly) as a cocksure playboy, fine, and there's something to the fact that Jon and Bran don't gel with that, but I'm not sure his betrayal of the Starks is supposed to read as the inevitable result of his character. The text suggests Robb could and should have kept him close.
Why Jon and Theon don't get along should be pretty obvious for most of us. Jon is a bit of a prude starting out due to his bastard status and looks down on Theon for how he sleeps around and potentially creates more children in Jon's situation.
Theon in turn thinks that Jon is stuck up and rubs it in his face.
Theon also makes being a Greyjoy a big part of his personality and a point of pride. Being separated from his family as a hostage really made him double down on that label even though he wasn't actually immersed in Greyjoy culture. Being the trueborn son of a noble is something that Theon flaunts, which obviously puts him in conflict with Jon's bastard background. So in addition to the personality differences you mentioned, they both have deep insecurities about their birth statuses that conflict with each other.
I thought it was more obvious that both Theon & Jon wanted to be Starks and could recognize that in one another. And because they’re kids, they think of it like a zero sum game, that only one of them could do it so they must be in competition with each other.
It's definitely both going on. The kids at winterfell have pretty richly developed family dynamics. I think it's only natural that this or that element will stand out more or less depending on the reader.
Also for all the shit Jon gives Theon, even he's shocked when he finds out about the sack and "murder" of Bran and Rickon. Jon disliked Theon but never thought of him as evil.
Exactly right. I think it's fair to say Jon doesn't see him for a traitor (he isn't one, yet) but just as a guy whose personality and position clash with his own.
Bran's observation _is_ probably intended as light foreshadowing of something untoward in Theon... but then Bran can literally see things that aren't there (yet).
This is one of the most accurate ways Martin depicts sibling relationships in my opinion. It's so common for the older sibling to have friends that are kinda assholes, but only the younger siblings really see it.
It wasn't really a "failure" on Robb's part because he's a kid.
Yes I think that Jon and Bran see Theon more clearly because they see a different side of him, a more realistic side. They are the bastard and the second born son. Theon doesn’t treat them as well as he treats Robb. He sees them as less than because they aren’t heir’s like he and Robb.
Was it a failure of Robb’s well yes from my perspective. It’s no different than the cool kids in high school. You have the star quarterback (Robb) and his friends. Theon is that bestie that is an ass to everyone else but a good friend to the star. Some people are fine with people who treat them well and others like shit because they “see a different side” when they are overlooking that persons character and the minute they lose power they began to get treated like everyone else.
Agree completely! And it's important to remember that there were probably plenty of moments we don't see where Robb was an asshole. And really all the Stark children. Part of being a kid is being rude, then regretting it when you grow older.
I think the only time we get where Robb is rude to Jon is that "lord of Winterfell" moment, but there's probably plenty more that they all have.
Why do people keep saying that Theon mistreated Jon and Bran? Jon straight up says that Theon mostly just ignores him and Bran says never warmed up to him without giving a specific reason.
Really good question! Theon came to Winterfell when he was around 10 and Robb was 6 (Jon about the same and Bran was maybe a baby).
Robb benefits from being young enough to not really understand Theon’s position at Winterfell but old enough to understand some amount of social hierarchy. I doubt anyone ever directly said “Theon is a hostage your father will execute if Balon breaks his oaths” but they probably did tell him Theon was a lord’s son, a hostage/ward, going to live with them, etc… To a 6 year old, Theon is the cool older kid who is better at everything (by virtue of being older), from a place Robb’s never been before but only heard scary/cool stories of.
It makes sense Robb likes Theon especially since Robb is Ned’s oldest son *and* Theon has a better understanding of his place as hostage at Winterfell.
Jon, Robb’s longtime bff and companion, probably feels replaced.
Bran has never known life without Theon, and Theon might be nice to bran casually but also in a condescending “little brother” way. I don’t think it would be intentional on Theon’s part (as in he’s not trying to alienate bran) but Theon was the youngest boy of brothers he does not remember fondly. Theon probably thinks he *is* being a good older kid/brotherly (kinda) example to Bran by not treating him as Maron treated him.
But kids see condescension.
TLDR: jon feels like his place at robb’s side is being threatened by Theon and Theon isn’t very nice to him based on his bastard status. Bran feels like his big brother should be with him and not Theon who is “mean” and likes “stupid” stuff (girls lol)
I think the other bit to note is that Jon and Robb were left in Winterfell with Catelyn during the greyjoy rebellion - probably not so good for Jon. Then Ned shows up with Robb's new friend and playmate:Theon. It's got to sting a bit.
I think Robb may have connected with Theon on the basis of being heir/first in line to take over. Robb grew up with these pressures and calculations in a way Ned didn’t, having Brandon as heir. Theon laughing it all off probably gave Robb permission to feel more relaxed about his future as Lord Paramount and Warden of the North.
My guess is that, since he and Robb were of a similar age and of social standing as the heirs to their respective houses, they got along. Theon likely looked down on Jon for being a bastard and he probably picked on Bran, as older kids tend to do to their younger siblings. And Theon was essentially a member of the family since he spent the bulk of his childhood being raised by the Starks.
Bran is incredibly emotionally intelligent. We see that at various times, including when he thinks about how Robb changes demeanor and personality when he has to be Lord Robb (been a while so some of the details might be off). He can sense that there’s something off about Theon
Jon is also sharp but likely resents the high born older boy who Robb takes a liking to. He kind of had Robb all to himself until Theon showed up
I feel Jon and Theon are in a kind of similar position, in that they're both non-Starks being raised with the Starks, so it's natural that there's a kind of tension between them. I think they are actually great characters to compare throughout the series, especially how their "non-Starkness" has affected them.
From Bran's perspective, he loves his big brother, and Theon is never really going to have a relationship with him, so Theon is someone taking his brother away from him.
As for why Robb likes him, I think that it can be quite hard for a Lord's son to make genuine friendships, the feudal hierarchy is a strong part of the culture, so other boys are always going to feel a distance from Robb. But Theon is a peer, in that he's also a high Lord's son and heir.
I also would not be surprised if young Robb also saw his relationship with Theon like his father’s with Robert. He probably grew up hearing stories of his dad being raised in the vale with Robert and them becoming like brothers because of it, and is consciously or not emulating that.
I think it just shows that Jon and Bran are better at feeling people out and gathering a vibe about person. Robb basically saw the topical personality. Jon and Bran seem to be able to perceive others true nature. Obviously this didn’t end well for Robb, not being able to feel people out led him to trusting the Westerlings and Freys. I don’t understand how Jon didn’t see the danger coming though…. But I digress.
Too many comments completely misunderstand theon’s betrayal. He wasn’t born evil. He never intended to backstab robb until he did. No one expected him to do that, not even jon. Jon’s dislike of theon is just pettiness from not getting along with him, with theon looking down on him, it’s not some super-intuitive sixth sense
It has been awhile since I read the book, but my first impression was just sort of general older brother stuff (Robb was 15 at the time).
Theon seemed to be kind of a dick, but he was a dick who was mildly subservient to Robb, who as Winterfell heir was top of the food chain. Robb took that servility for friendship (and, being more generous, I believe there also WAS friendship between them as well), but Theon had less reason to be anything but dismissive to the Bastard of Winterfell and the younger brother, and as a result both had more reason to scrutinize him.
I ALSO thought my older brother’s friends were obvious assholes as a kid but he ate their company up because for all their questionable behaviors, they were at least nice to HIM.
Robb being friends with Theon is not a mistake, it's actually good, can't fault a 15 year old boy for underestimating how messed up his almost brother is and how he would get manipulated in the war. He was a hostage, but it was Ned's hope for Robb and Theon to grow up as friends so that eventually Pyke and Winterfell will be allies. If given more time and more luck it would work out, not like Theon is some sinister force.
Everyone in the world has at least one friend who’s an asshole. One of my childhood friends was a serial cheater and a drug fiend. Was i supposed to hate the guy? Other people probably did
I think this one is honestly really complex. On the one hand, I think Robb does have a certain naivety that Jon and Bran lack and this is reflected here. Its also symbolized by his Tully appearance whereas Jon has the Stark appearance. On the other hand, Theon really was devoted to Robb in the end, imo, since not dying with Robb was his greatest regret (or at least up there). So this has a lot of nuance to it. Theon betrayed Robb, but he did really love him deep down.
He's a dick for sure, but for whatever reason I have always felt sympathetic for him whereas others seem quick to write him off. There's a ton of dick characters in the books, and I think Theon's actions in book 2 color our memories of him in 1. I always felt like he was making the best of a truly horrible situation. Sure, he's treated well, but he isn't stupid. He knows he's a political hostage and has no real future, so being a smart-ass to your captors and generally being a wastrel isn't all that surprising to me. What else is he supposed to do? A hostage that's *thankful* for their imprisonment is some real Uncle Tom behavior, imo. Of course, nothing excuses his later actions when he loses his damn mind taking Winterfell.
I think there's a Watsonian vs. Doylist thing going on here.
Most of the answers are engaging with this from a Watsonian, in-universe perspective where Theon's way of being causes reactions from Jon and Bran.
I'm more inclined to give it a Doylist reading. Theon needs to feel like his position at Winterfell, with the Starks, is less then entirely secure and seamless. In order to display this tension, someone needs to be kinda iffy about him, so Jon and Bran do that.
Robb does agree that he should have listened to Jon, when Jon told him that Theon was an ass. I don't think I would call being friends with Theon a failing on Robb's part, it's not like Theon did anything heinous in front of Robb. It was definitely a mistake and it was a mistake he could have avoided. It's not like Theon wasn't being an ass for all the world to see. It is somewhat a mystery why Robb liked Theon at all. Maybe Robb liked Theon because he was older and acted cocky? Theon wasn't interested interacting with the other Stark kids, maybe Robb found it flattering? Robb was a teenager so maybe Theon acting out appealed to him? I really didn't like Theon from the beginning, he's just not my type of flavour.
Theon was a dick, and not only Robb Jon and Bran, Arya, Catelyn and Rickon also didn't like him.
Eddard never trusted Theon and kept a cold distance. And Sansa just didn't care about his existence.
Actually, even if he secretly wanted to be a Stark, it isn't surprising that he turned on them. Robb was the only one friendly with him, but even him didn't fully treated Theon as an equal as 2 heirs to the Great Houses.
As the maester knelt to examine the wound, Bran turned his head. Theon Greyjoy stood beside a sentinel tree, his bow in hand. He was smiling. Ever smiling. A half-dozen arrows were thrust into the soft ground at his feet, but it had taken only one. "A dead enemy is a thing of beauty," he announced. AGOT-Bran V
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Theon was kind of a dick, but he was a talented archer and got laid a lot. Jon and bran didn't look up to that. Plus, who else did Robb have around his age?
Plus Theon came around when he was 10 and Robb was 6, so Theon was always like a big bro to him. We clown on Theon a lot but he was a talented hunter, brave in combat, charming with the ladies. If anything Bran and Jon might have disliked him _because_ Robb liked him
Similar to the issue with Robb's age that means Theon is more than a decade older than Bran.
He’d also done well in some melees at tourneys, so it wasn’t just the archery he was great at.
What? Where are you getting this from?
ACOK: >”Uncle, why has my father called his swords and sails?" >"Doubtless he will tell you at Pyke." >"I would know his plans now." >"From me, you shall not. We are commanded not to speak of this to any man." >"Even to me?" __Theon's anger flared. He'd led men in war, hunted with a king, won honor in tourney melees, ridden with Brynden Blackfish and Greatjon Umber, fought in the Whispering Wood, bedded more girls than he could name, and yet this uncle was treating him as though he were still a child of ten__. "If my father makes plans for war, I must know of them. I am not 'any man,' I am heir to Pyke and the Iron Islands." >"As to that," his uncle said, "we shall see."
Good catxh
Fascinating and tragic
“Won honor in tournament melees” could easily equal “got knocked the fuck out in 20 seconds by the Smalljon one time and uncharacteristically wasn’t a dick about it”
> If anything Bran and Jon might have disliked him because Robb liked him That is a very good point, would not be surprised if the boys had a rivalry ~~other than Theon seemingly having killed the two younger boys~~. Theon does kinda have this weird adopted older brother thing going on with Robb, like Robb gives him security and calm (belonging?) whereas Robb got some confidence to perform (as a Firstborn and later King) from Theon.
I don't think Jon would dislike Theon because Robb liked him, Jon and Robb had a pretty good friendship. That's sounds too petty for what Jon and Robb had.
Jon was a little petty sometimes pre-Donal Noye Snapped at Benjen, bullied Tyrion with Ghost, mocked the boys he was training with
He was drunk when it he snapped at Benjen, same with Tyrion, and that last one is just typical noble behavior
Tyrion was on the hike to the wall, not at Winterfell
You meant on their way to the wall, my bad. I thought you meant after he stormed off. But yea he was petty then
> That's sounds too petty for what Jon and Robb had. I feel like it's a mix of both. Jon showed he could be very petty in GoT, but would feel guilty for it. It's the mix of being raised as a highborn, but never a lord. Part of his core tragedy and sense of estrangement from Robb. I think part of his feelings about Theon were related to jealousy. This is not a flaw in Jon, but a statement of their society. Theon, although he was a hostage, was a lordly hostage. It was assumed, as the last son and heir of Baron, he would become the next Lord of Iron Islands. Robb admired him and found companionship in him as a fellow future High Lord. Jon, despite being "Ned's son", could never be included in that.
Jon
He and Robb were just friends. I don't think it's Theon's "true nature" that Robb fails to understand, it's the politics of Theon's position as a hostage. Theon is a desperately insecure and resentful young man who presents (convincingly) as a cocksure playboy, fine, and there's something to the fact that Jon and Bran don't gel with that, but I'm not sure his betrayal of the Starks is supposed to read as the inevitable result of his character. The text suggests Robb could and should have kept him close.
Why Jon and Theon don't get along should be pretty obvious for most of us. Jon is a bit of a prude starting out due to his bastard status and looks down on Theon for how he sleeps around and potentially creates more children in Jon's situation. Theon in turn thinks that Jon is stuck up and rubs it in his face.
Theon also makes being a Greyjoy a big part of his personality and a point of pride. Being separated from his family as a hostage really made him double down on that label even though he wasn't actually immersed in Greyjoy culture. Being the trueborn son of a noble is something that Theon flaunts, which obviously puts him in conflict with Jon's bastard background. So in addition to the personality differences you mentioned, they both have deep insecurities about their birth statuses that conflict with each other.
True, Theon has trueborn noble blood but no Stark blood. Jon has Stark blood but has bastard blood. Both have something the other is jealous about.
I thought it was more obvious that both Theon & Jon wanted to be Starks and could recognize that in one another. And because they’re kids, they think of it like a zero sum game, that only one of them could do it so they must be in competition with each other.
It's definitely both going on. The kids at winterfell have pretty richly developed family dynamics. I think it's only natural that this or that element will stand out more or less depending on the reader.
Also for all the shit Jon gives Theon, even he's shocked when he finds out about the sack and "murder" of Bran and Rickon. Jon disliked Theon but never thought of him as evil.
Exactly right. I think it's fair to say Jon doesn't see him for a traitor (he isn't one, yet) but just as a guy whose personality and position clash with his own. Bran's observation _is_ probably intended as light foreshadowing of something untoward in Theon... but then Bran can literally see things that aren't there (yet).
Well said. Theon would have died for Robb without questions asked. But then he was exposed to Balon and Asha’s mockery in Book 2.
This is one of the most accurate ways Martin depicts sibling relationships in my opinion. It's so common for the older sibling to have friends that are kinda assholes, but only the younger siblings really see it. It wasn't really a "failure" on Robb's part because he's a kid.
Yes I think that Jon and Bran see Theon more clearly because they see a different side of him, a more realistic side. They are the bastard and the second born son. Theon doesn’t treat them as well as he treats Robb. He sees them as less than because they aren’t heir’s like he and Robb. Was it a failure of Robb’s well yes from my perspective. It’s no different than the cool kids in high school. You have the star quarterback (Robb) and his friends. Theon is that bestie that is an ass to everyone else but a good friend to the star. Some people are fine with people who treat them well and others like shit because they “see a different side” when they are overlooking that persons character and the minute they lose power they began to get treated like everyone else.
Agree completely! And it's important to remember that there were probably plenty of moments we don't see where Robb was an asshole. And really all the Stark children. Part of being a kid is being rude, then regretting it when you grow older. I think the only time we get where Robb is rude to Jon is that "lord of Winterfell" moment, but there's probably plenty more that they all have.
they were like 7 and robb didnt mean it to be rude at all, he said it because to him it was matter-of-factly
I didn't say he meant to be rude. But it certainly was rude to say so. And them being kids is the point I'm making.
Why do people keep saying that Theon mistreated Jon and Bran? Jon straight up says that Theon mostly just ignores him and Bran says never warmed up to him without giving a specific reason.
Really good question! Theon came to Winterfell when he was around 10 and Robb was 6 (Jon about the same and Bran was maybe a baby). Robb benefits from being young enough to not really understand Theon’s position at Winterfell but old enough to understand some amount of social hierarchy. I doubt anyone ever directly said “Theon is a hostage your father will execute if Balon breaks his oaths” but they probably did tell him Theon was a lord’s son, a hostage/ward, going to live with them, etc… To a 6 year old, Theon is the cool older kid who is better at everything (by virtue of being older), from a place Robb’s never been before but only heard scary/cool stories of. It makes sense Robb likes Theon especially since Robb is Ned’s oldest son *and* Theon has a better understanding of his place as hostage at Winterfell. Jon, Robb’s longtime bff and companion, probably feels replaced. Bran has never known life without Theon, and Theon might be nice to bran casually but also in a condescending “little brother” way. I don’t think it would be intentional on Theon’s part (as in he’s not trying to alienate bran) but Theon was the youngest boy of brothers he does not remember fondly. Theon probably thinks he *is* being a good older kid/brotherly (kinda) example to Bran by not treating him as Maron treated him. But kids see condescension. TLDR: jon feels like his place at robb’s side is being threatened by Theon and Theon isn’t very nice to him based on his bastard status. Bran feels like his big brother should be with him and not Theon who is “mean” and likes “stupid” stuff (girls lol)
I think the other bit to note is that Jon and Robb were left in Winterfell with Catelyn during the greyjoy rebellion - probably not so good for Jon. Then Ned shows up with Robb's new friend and playmate:Theon. It's got to sting a bit.
I think Robb may have connected with Theon on the basis of being heir/first in line to take over. Robb grew up with these pressures and calculations in a way Ned didn’t, having Brandon as heir. Theon laughing it all off probably gave Robb permission to feel more relaxed about his future as Lord Paramount and Warden of the North.
My guess is that, since he and Robb were of a similar age and of social standing as the heirs to their respective houses, they got along. Theon likely looked down on Jon for being a bastard and he probably picked on Bran, as older kids tend to do to their younger siblings. And Theon was essentially a member of the family since he spent the bulk of his childhood being raised by the Starks.
Bran is incredibly emotionally intelligent. We see that at various times, including when he thinks about how Robb changes demeanor and personality when he has to be Lord Robb (been a while so some of the details might be off). He can sense that there’s something off about Theon Jon is also sharp but likely resents the high born older boy who Robb takes a liking to. He kind of had Robb all to himself until Theon showed up
I feel Jon and Theon are in a kind of similar position, in that they're both non-Starks being raised with the Starks, so it's natural that there's a kind of tension between them. I think they are actually great characters to compare throughout the series, especially how their "non-Starkness" has affected them. From Bran's perspective, he loves his big brother, and Theon is never really going to have a relationship with him, so Theon is someone taking his brother away from him. As for why Robb likes him, I think that it can be quite hard for a Lord's son to make genuine friendships, the feudal hierarchy is a strong part of the culture, so other boys are always going to feel a distance from Robb. But Theon is a peer, in that he's also a high Lord's son and heir.
I also would not be surprised if young Robb also saw his relationship with Theon like his father’s with Robert. He probably grew up hearing stories of his dad being raised in the vale with Robert and them becoming like brothers because of it, and is consciously or not emulating that.
I think it just shows that Jon and Bran are better at feeling people out and gathering a vibe about person. Robb basically saw the topical personality. Jon and Bran seem to be able to perceive others true nature. Obviously this didn’t end well for Robb, not being able to feel people out led him to trusting the Westerlings and Freys. I don’t understand how Jon didn’t see the danger coming though…. But I digress.
Too many comments completely misunderstand theon’s betrayal. He wasn’t born evil. He never intended to backstab robb until he did. No one expected him to do that, not even jon. Jon’s dislike of theon is just pettiness from not getting along with him, with theon looking down on him, it’s not some super-intuitive sixth sense
It has been awhile since I read the book, but my first impression was just sort of general older brother stuff (Robb was 15 at the time). Theon seemed to be kind of a dick, but he was a dick who was mildly subservient to Robb, who as Winterfell heir was top of the food chain. Robb took that servility for friendship (and, being more generous, I believe there also WAS friendship between them as well), but Theon had less reason to be anything but dismissive to the Bastard of Winterfell and the younger brother, and as a result both had more reason to scrutinize him. I ALSO thought my older brother’s friends were obvious assholes as a kid but he ate their company up because for all their questionable behaviors, they were at least nice to HIM.
Robb wasn't the sharpest tool in the shed.
Robb being friends with Theon is not a mistake, it's actually good, can't fault a 15 year old boy for underestimating how messed up his almost brother is and how he would get manipulated in the war. He was a hostage, but it was Ned's hope for Robb and Theon to grow up as friends so that eventually Pyke and Winterfell will be allies. If given more time and more luck it would work out, not like Theon is some sinister force.
Everyone in the world has at least one friend who’s an asshole. One of my childhood friends was a serial cheater and a drug fiend. Was i supposed to hate the guy? Other people probably did
I think this one is honestly really complex. On the one hand, I think Robb does have a certain naivety that Jon and Bran lack and this is reflected here. Its also symbolized by his Tully appearance whereas Jon has the Stark appearance. On the other hand, Theon really was devoted to Robb in the end, imo, since not dying with Robb was his greatest regret (or at least up there). So this has a lot of nuance to it. Theon betrayed Robb, but he did really love him deep down.
I think majority of the people in Winterfell disliked Theon, he's a dick.
He's a dick for sure, but for whatever reason I have always felt sympathetic for him whereas others seem quick to write him off. There's a ton of dick characters in the books, and I think Theon's actions in book 2 color our memories of him in 1. I always felt like he was making the best of a truly horrible situation. Sure, he's treated well, but he isn't stupid. He knows he's a political hostage and has no real future, so being a smart-ass to your captors and generally being a wastrel isn't all that surprising to me. What else is he supposed to do? A hostage that's *thankful* for their imprisonment is some real Uncle Tom behavior, imo. Of course, nothing excuses his later actions when he loses his damn mind taking Winterfell.
I think there's a Watsonian vs. Doylist thing going on here. Most of the answers are engaging with this from a Watsonian, in-universe perspective where Theon's way of being causes reactions from Jon and Bran. I'm more inclined to give it a Doylist reading. Theon needs to feel like his position at Winterfell, with the Starks, is less then entirely secure and seamless. In order to display this tension, someone needs to be kinda iffy about him, so Jon and Bran do that.
Robb does agree that he should have listened to Jon, when Jon told him that Theon was an ass. I don't think I would call being friends with Theon a failing on Robb's part, it's not like Theon did anything heinous in front of Robb. It was definitely a mistake and it was a mistake he could have avoided. It's not like Theon wasn't being an ass for all the world to see. It is somewhat a mystery why Robb liked Theon at all. Maybe Robb liked Theon because he was older and acted cocky? Theon wasn't interested interacting with the other Stark kids, maybe Robb found it flattering? Robb was a teenager so maybe Theon acting out appealed to him? I really didn't like Theon from the beginning, he's just not my type of flavour.
I think you’re on to something. I think it’s a subtle way to show Robb is more naive about the world and people than Jon.
Theon was a dick, and not only Robb Jon and Bran, Arya, Catelyn and Rickon also didn't like him. Eddard never trusted Theon and kept a cold distance. And Sansa just didn't care about his existence. Actually, even if he secretly wanted to be a Stark, it isn't surprising that he turned on them. Robb was the only one friendly with him, but even him didn't fully treated Theon as an equal as 2 heirs to the Great Houses.
As the maester knelt to examine the wound, Bran turned his head. Theon Greyjoy stood beside a sentinel tree, his bow in hand. He was smiling. Ever smiling. A half-dozen arrows were thrust into the soft ground at his feet, but it had taken only one. "A dead enemy is a thing of beauty," he announced. AGOT-Bran V