“If Stannis can raise the north …” Sam hesitated, then said, “The Lannisters have northmen of their own. Lord Bolton and his bastard.” (JON II) Your false king is dead, bastard. He and all his host were smashed in seven days of battle. I have his magic sword. (JON XIII)

The first temptations that Martin presents Jon with in ADWD involve Stannis Baratheon. Jon must decide what help, if any, he can give Stannis in his invasion of the North, while maintaining the independence and neutrality of the Night’s Watch. Overall, Jon’s thoughts and behavior toward Stannis undergo a progression — in his early chapters, he is conflicted and reluctant to take sides in the game of thrones. But as things go on, his thoughts gets less conflicted, and he finds himself clearly rooting for Stannis, fails to create any distance between them, and helps him in a variety of covert ways.

Through it all, Jon does nearly nothing to prepare for the always-distinct possibility that Stannis will lose. Whether the Pink Letter is true or false, its effect in the moment is to vividly bring that possibility alive.

Can Stannis Win?

Leaving vows aside for the moment, there are many good, practical, noble reasons why Jon would want to help Stannis. (1) Stannis saved the Watch so they owe him a great deal, (2) Stannis is the only king who cares about stopping the Others, (3) Jon can win various aid from Stannis that will help him defend the realm, (4) Stannis would be better for the people of the North than the evil and cruel Boltons or ironborn, (5) Though Stannis’ forces are small, he does outnumber the Watch men at the moment and could use force to get his way.

But there is one very good practical reason why Jon shouldn’t help Stannis — Stannis might lose! Indeed, given the information Jon has, Stannis looks extremely likely to lose.

Here are the facts at this point. Stannis has a mere 1,500 men, and (according to Jon) the two Bolton armies would outnumber him “five to one.” Every family in the North has rejected Stannis’ entreaties except for Arnolf Karstark (who we later find out is treacherous). He has no particular knowledge of the territory, while his adversaries grew up there. As if his Northern situation wasn’t bad enough, his southern situation is beyond grim, as he has practically no remaining support there, let alone love. Instead he is an attainted traitor and rebel against the Iron Throne, which is currently controlled by the continent’s two richest families, families who have already managed to put down open military resistance in every other kingdom, and who together could have the capacity to field an army greater than 100,000.

Confronting the probability that Stannis will lose isn’t weak or cowardly. Jon, as Lord Commander, is charged with the tremendous responsibility of protecting humanity from the Others. If he becomes too closely associated with a failed rebel lord, there will be retaliation against the Watch and he will likely fail in that larger duty. So he has a responsibility to prepare for this outcome. Martin has characters point this out to Jon at least twice, and both times Jon is uninterested in contemplating it, preferring instead to speculate about how Stannis might win. First, with Sam:

“If the Lannisters should prevail and Lord Tywin decides that we betrayed the king by aiding Stannis, it could mean the end of the Night’s Watch. He has the Tyrells behind him, with all the strength of Highgarden. And he did defeat Lord Stannis on the Blackwater.” “The Blackwater was one battle. Robb won all his battles and still lost his head. If Stannis can raise the north …” Sam hesitated, then said, “The Lannisters have northmen of their own. Lord Bolton and his bastard.” “Stannis has the Karstarks. If he can win White Harbor …” “If,” Sam stressed. “If not…” (JON II)

Later, Bowen Marsh makes the same point. While many readers ascribe Marsh’s eventual betrayal of Jon to his anti-wildling bigotry, this establishes early in the book that Marsh greatly fears the consequences of a Stannis defeat.

“Lord Stannis helped us when we needed help,” Marsh said doggedly, “but he is still a rebel, and his cause is doomed. As doomed as we’ll be if the Iron Throne marks us down as traitors. We must be certain that we do not choose the losing side.” “It is not my intent to choose any side,” said Jon, “but I am not as certain of the outcome of this war as you seem to be, my lord. Not with Lord Tywin dead… The lion in King’s Landing is a cub, and the Iron Throne has been known to cut grown men to ribbons.” “A boy he may be, my lord, but … King Robert was well loved, and most men still accept that Tommen is his son. The more they see of Lord Stannis the less they love him, and fewer still are fond of Lady Melisandre with her fires and this grim red god of hers. They complain.” “They complained about Lord Commander Mormont too. Men love to complain about their wives and lords, he told me once. Those without wives complain twice as much about their lords.” (JON III)

Martin puts these prescient warnings early in the book, and the Pink Letter seemingly vindicates them. Marsh’s worst fears are confirmed, and his assassination attempt against Jon follows. Now, the Pink Letter could well be inaccurate, and it remains quite possible that Stannis will actually defeat the Boltons (though that still doesn’t solve the problem of the Iron Throne). But that wouldn’t mean Jon’s close association with Stannis was the “right” decision, especially considering the stakes involved — the potential destruction of the Watch. Given Stannis’ immensely disadvantaged situation at the start, it would mean that Jon made an incredibly risky gamble with the fate of humanity, and got lucky. But the Pink Letter forces Jon to reckon with the outcome that was most likely all along.

The Paper Shield

As Lord Commander, it was Jon’s responsibility to prepare for the possibility of a Lannister/Bolton victory — and he spends amazingly little time doing this. Why? Let’s look at the one time Jon does give this issue any thought:

Jon Snow read the letter over until the words began to blur and run together. I cannot sign this. I will not sign this. He almost burned the parchment then and there. Instead he took a sip of ale, the dregs of the half cup that remained from his solitary supper the night before. I have to sign it. They chose me to be their lord commander. The Wall is mine, and the Watch as well. The Night’s Watch takes no part. (JON II)

Jon is so intensely revolted by the following letter that Maester Aemon has suggested he send to King Tommen:

“The Night’s Watch takes no part in the wars of the Seven Kingdoms. Our oaths are sworn to the realm, and the realm now stands in dire peril. Stannis Baratheon aids us against our foes from beyond the Wall, though we are not his men …” Sam squirmed in his seat. “Well, we’re not. Are we?” (JON II)

As Sam points out, there is nothing whatsoever wrong with the text of this letter, which merely reaffirms the longstanding neutrality of the Watch. Jon’s outrage about it is an amazing overreaction, considering he is charged with the fate of humanity.

“I gave Stannis food, shelter, and the Nightfort, plus leave to settle some free folk in the Gift. That’s all.” “Lord Tywin will say it was too much.” “Stannis says it’s not enough. The more you give a king, the more he wants. We are walking on a bridge of ice with an abyss on either side. Pleasing one king is difficult enough. Pleasing two is hardly possible.” (JON II)

Jon doesn’t want to bother trying to please the Iron Throne. But is it truly just because it’s hard to please two kings? Or are there more personal reasons?

“At Winterfell, Tommen fought my brother Bran with wooden swords,” Jon said, remembering. “He wore so much padding he looked like a stuffed goose. Bran knocked him to the ground.” He went to the window and threw the shutters open. The air outside was cold and bracing, though the sky was a dull grey. “Yet Bran’s dead, and pudgy pink-faced Tommen is sitting on the Iron Throne, with a crown nestled amongst his golden curls…” “…[Lord Tywin] will not want it said that Stannis rode to the defense of the realm whilst King Tommen was playing with his toys. That would bring scorn down upon House Lannister.” “It’s death and destruction I want to bring down upon House Lannister, not scorn.” (JON II)

It’s clear that, though Jon attempted to forswear the North in favor of the Wall, he still intensely hates the Lannisters for their role in his family’s downfall and desperately wants them to fall. (Another sign of this is that Jon always refers to “King Stannis” in his thoughts, yet in the quotes in the previous section, Sam and Bowen both use “Lord Stannis” instead.) In this case, Jon is so furiously resistant over a mere declaration of neutrality. Only the good advice of Sam and Aemon manages to twist Jon’s arm into signing this near-meaningless gesture that costs him nothing:

“Stannis has the Karstarks. If he can win White Harbor …” “If,” Sam stressed. “If not … my lord, even a paper shield is better than none.” “I suppose so.” Him and Aemon both. Somehow he had hoped that Sam Tarly might see it differently. It is only ink and parchment. Resigned, he grabbed the quill and signed. (JON II)

Sam and Aemon leave later that chapter, and Jon never spends much time thinking about the issue again. Until the Pink Letter arrives.

Jon’s Aid to Stannis

Now, toward the beginning of the book, Jon did often try to chart an independent course for himself and the Watch, with regards to Stannis:

“Have you signed the grant?” “No, Your Grace.” And now it comes. Jon closed his burned fingers and opened them again. “You ask too much.” …“Your Grace,” said Jon, with chilly courtesy, “I have housed your men and fed them, at dire cost to our winter stores. I have clothed them so they would not freeze.” Stannis was not appeased. “Aye, you’ve shared your salt pork and porridge, and you’ve thrown us some black rags to keep us warm. Rags the wildlings would have taken off your corpses if I had not come north.” Jon ignored that. “I have given you fodder for your horses, and once the stair is done I will lend you builders to restore the Nightfort. I have even agreed to allow you to settle wildlings on the Gift, which was given to the Night’s Watch in perpetuity…. The stones of those forts are mortared with the blood and bones of my brothers, long dead. I cannot give them to you… I took an oath, Your Grace. The Wall is mine.” (JON I)

But in Jon’s fourth chapter, he changes. Rather than standing firm again, he starts giving in to his temptations to influence the war in the North:

King Stannis said, “Lord Snow, tell me of Mors Umber.” The Night’s Watch takes no part, Jon thought, but another voice within him said, Words are not swords. “The elder of the Greatjon’s uncles. Crow-food, they call him… …”Once Lord Roose has joined his strength to Ramsay’s, they will have you outnumbered five to one… Sire, this is a bold stroke, but the risk—” The Night’s Watch takes no part. Baratheon or Bolton should be the same to me. “If Roose Bolton should catch you beneath his walls with his main strength, it will be the end for all of you.” …Jon realized that his words were wasted. Stannis would take the Dreadfort or die in the attempt. The Night’s Watch takes no part, a voice said, but another replied, Stannis fights for the realm, the ironmen for thralls and plunder. “Your Grace, I know where you might find more men. Give me the wildlings, and I will gladly tell you where and how.” (JON IV)

This scene is an immensely important turning point for Stannis’ fortunes, since if Jon had said nothing, Stannis would have marched straight into a trap at the Dreadfort and died. Also, Jon’s suggestion of wooing the mountain clans will end up tripling Stannis’ strength.

EDIT: As pointed out by poster “Here Me Meow” on Westeros.org, the consequences of Jon’s actions here are even more significant than that — to the best of Jon’s knowledge here, his advice will avert a quick end to the Northern civil war, and ensure a longer, more grueling struggle which will weaken both sides, in hopes that his preferred underdog contender will emerge triumphant.

It’s a very important turning point for Jon as well. Now, this was all advice given in private, so I don’t think the advice itself placed the Watch at any risk, or had a real role in Jon’s downfall. But the scene is significant because it shows Jon repeatedly batting away the voice telling him “the Watch takes no part” — a voice he will listen less and less to as the book continues. It is an early example of how, rather than putting the realm aside, Jon is starting to use his newfound power to try to achieve things he wants there — “to set the world to rights.” This will become more and more significant as his arc continues.

Deeper and Deeper

Later in the book, Jon finds himself “rooting” for Stannis more and more, though this is often tinged with guilt:

“Lord Snow?” a soft voice said. He turned to find Clydas standing beneath the broken archway, a parchment in his hand. “From Stannis?” Jon had been hoping for some word from the king. The Night’s Watch took no part, he knew, and it should not matter to him which king emerged triumphant. Somehow it did. (JON VI) …Stannis had taken Deepwood Motte, and the mountain clans had joined him. Flint, Norrey, Wull, Liddle, all…. The Night’s Watch was sworn to take no side in the quarrels and conflicts of the realm. Nonetheless, Jon Snow could not help but feel a certain satisfaction. (JON VII)

Jon also allows Selyse to move into Castle Black, and is frequently seen consulting with Melisandre. Perceptions like this are important, especially because since the paper shield, Jon has done nothing to create the perception of distance between himself and Stannis’ camp, not even another symbolic gesture. He even eventually orchestrates a wedding with Mel and Selyse. By the middle of the book, word has clearly reached the Boltons that Jon is basically working with Stannis:

Theon shivered. Baratheon or Bolton, it made no matter to him. Stannis had made common cause with Jon Snow at the Wall, and Jon would take his head off in a heartbeat. (THEON VI)

Jon’s political project to allow Tormund’s wildlings through the Wall provides another reason for him to wishfully hope Stannis will succeed:

“This is no game. A river of blood runs between our peoples, old and deep and red. Stannis Baratheon is one of the few who favors admitting wildlings to the realm. I need his queen’s support for what I’ve done.” (JON XI)

All this while, Jon is haunted by brief thoughts that Stannis could lose, but he still does nothing to plan for that possibility:

“I can provide you with horses, provisions, guides, whatever is required to get you as far as Deepwood Motte. From there you will need to make your own way to Stannis.” And you may well find his head upon a spike. (JON IX) “A northern maid and a wildling warrior, bound together by the Lord of Light.” Ser Axell Florent slipped into Lady Alys’s vacant seat. “Her Grace approves. I am close to her, my lord, so I know her mind. King Stannis will approve as well.” Unless Roose Bolton has stuck his head on a spear. (JON X) “I see you have considered all this carefully, Lord Snow. I am sure King Stannis will be pleased when he returns triumphant from his battle.” Assuming he returns at all. (JON XI)

Finally, once Alys Karstark arrives at the Wall with the news that her uncle is working with the Boltons, Jon is faced with one more choice. And offscreen, he quickly sends a raven to Stannis to warn him:

Clydas had dispatched a raven to Deepwood Motte to warn the king of Arnolf Karstark’s treachery, but whether the bird had reached His Grace in time Jon did not know. (JON X)

It seems Jon is no longer very conflicted about doing such things. He’s all in with Stannis.

Conclusion

In ADWD, Martin starts giving Jon moral dilemmas that are more complicated than “Should I stay or should I go?” Jon has many good reasons to help Stannis conquer the North — along with his rather less noble hatred of the Lannisters and Boltons. But Jon fails to prepare for the very real possibility that Stannis could lose, and fails to create enough distance between himself and Stannis. These failures place the Watch at great risk, and Martin uses the Pink Letter to make that very clear.

Jon’s actions toward Stannis are significant for another reason. Rather than putting the matters of the realm aside to focus on the Watch’s larger purpose and struggle, Jon started indulging his impulse to try and set the world to rights in the North. This impulse is untenable with his role as Lord Commander, and will eventually lead to dire consequences for the Watch.

Next: “All to save my sister”