Enlightening essays on Dany and Jon- ADWD (New Jon essay)

[lojzelote]

Wonderful essays on Dany and Jon both. I agree with the author in nearly everything.I must say I've never paid much mind

to that advice by the Old Bear. It makes so much sense now. GRRM is a master of continuity and long-term plotting.. :bowdown:

I'm just ducking in here to say that I think it's a rather huge mistake to make judgment calls on Jon's leadership based on what's in the Pink Letter when we have very good reason to believe it's not true. Saying that the Pink Letter is some comeuppance or consequence of Jon's actions up until now really only fits if the Pink Letter was actually written by Ramsay and if Stannis has actually lost and is dead. Very few people I know on here believe that both of those things are true — most think it's a bluff, that Stannis is faking his death and/or that Ramsay didn't even write the damn thing. If the stabbing is a consequence of the letter, same story: We don't truly know why it was done, or what will come of it. It's hardly a consequence of poor decision-making for Jon to get stabbed and then resurrected as some deity-like figure, no more so than it was a consequence for Dany to trust MMD and get dragons out of it.

I believe Adam addresses it perfectly; even if what is written in the letter isn't true because Ramsay's been misinformed about the battle with Stannis, it still shows what would happen in the very realistic scenario that Jon's gamble could go wrong (and speaking of Jon's actions regarding "Arya", it almost certainly went wrong, given that Mance and/or the spearwives were taken and tortured and gave away the information of Jon's involvement in the scheme to help Ramsay's bride escape the marriage).

As for whether Ramsay's truly written it ... None of those alternative theories make any sense. Really, I've never seen any of them satisfyingly explain why Stannis/Mance/Theon/Asha/whoever else would write Jon such a letter. Most give as a reason that the author needed Jon's help. But if you need somebody's help, you don't write them a letter pretending you're the enemy and that the real you is dead and it's all over already; it's more likely your ally will give up and agree to the terms rather than fight for what you portray as a hopelessly lost case. Why not simply write a normal letter to inform him of the situation and indicate you'd welcome his aid? Not to mention, if the Pink Letter lies, and majority of the Northmen turned against the Boltons as most readers believe, nobody really needs Jon's help in the first place. So why troll him with a piece of psycho writing?

It's clear what the Pink Letter, respective Jon's reaction to it led to - to Jon being stabbed by his brothers. So yeah, it's definitely a direct consequence of his actions, whether one views them as poor or not. What the stabbing will lead to regarding his possible resurrection is quite another question. Jon does not see himself as a candidate for AAR, so how to do it that he would be reborn amidst smoke and salt never played a part in his calculations, therefore it would happen as a completely unintended, unforeseeable byproduct of his actions. OTOH, he must have been aware that going against the Boltons and some of his sworn brothers might not end well for him; it was nowhere near as ... obscure, quite the opposite.

[Adam Feldman]

It would have been helpful to focus more on their dynamic and interplay and less on the hand-wringing over whether Jon was breaking his vows or not

My essays about how GRRM structures his character arcs to give his characters' dilemmas of values. They are not about how x character or y character is awesome and competent. There is much that Jon does that is incredibly brilliant and competent, but it's not my focus here. I must also say that I don't understand the instinct to minimize or sweep away these conflicts of values. They are the heart of the series, as Martin himself has said many times. I in fact did not focus on vow-breaking "hand-wringing" and specifically avoided it, in favor of examining whether Jon's overall conduct re: Stannis was an unwise practical risk to take for the Watch and the larger struggle.

You also assume that some version of the pink letter isn't coming when Stannis lost regardless of what Jon does.

if Stannis doesn't save the realm, the realm doesn't get saved.

Jon really didn't have a choice in aiding Stannis.

Neutrality isn't really an option for the NW, as the story goes on… . I see Jon's behaviour towards Stannis as the only sensible course of action.

I also agree that neutrality at this point is impossible… And the neutrality goes both ways. It is not that the Watch should bend over to every passing nutcase just to remain impartial.

Which of these do you all disagree with:

1. A Stannis victory looked incredibly unlikely at the start of the book, since every Northern family but one had rejected him, the Boltons had 5 times his forces, they knew the terrain better, and beyond them there's the Iron Throne.

Since a Stannis defeat appears the likely outcome, the Lord Commander has the responsibility to affirmatively take measures to try to ensure the Watch can still function and fulfill its greater purpose of defending the realm if that likely outcome in fact happens.

Not only does Jon take no such measures (except the paper shield), but he doesn't even seen to plan for what he will do in the likely event of a Stannis defeat.

The Watch maintaining neutrality in the face of a Bolton victory surely would have been extremely difficult. But there are things Jon could have tried. At the very least he could have sent an emissary to the Boltons to clarify the Watch's policy of neutrality, something he never apparently considers. He also could have taken more affirmative steps to distance himself from Stannis, not let Selyse come to Castle Black, not hang out with Melisandre all the time, etc. There's no guarantee of success, but my point is that Jon doesn't try anything (except the paper shield when his arm is twisted) or even plan for anything, when the outcome is out of his control. Like I said, the Pink Letter being fake doesn't make Jon "right," it means he took a crazy risk and it happened to work out. If the ball happens to bounce his way and Stannis does win (helped by Jon's covert interventions), that doesn't get Jon off the hook for his failure to prepare or plan for the opposite scenario that was always distinctly possible.

Also, if GRRM's point was that it was pointless for Jon to remain neutral, it would have been quite easy for him to throw in a line in an early Reek chapter where a Bolton says, "And after we kill Stannis, we'll murder that Stark bastard at the Wall!" Yet there is nothing to that effect. Instead we get the early warnings that Jon needs to prepare for the possibility of a Stannis loss, and the Pink Letter seemingly vindicating those warnings. Which seems more suggestive of the author's intent, to me.

[butterbumps!]

I don't prefer the Jon essays. As I understand the fundamental premise, it's that Jon is torn between his desire to, essentially, be a knight, and his "ultimate purpose," which is to save the realm against external threats. I agree that this is a major tension, but I disagree with the subsequent points that follow, specifically about neutrality.

Even if one does not want to adopt the idea that "neutrality is a two-way street," it can't be denied that neutrality is a luxury of the strong. The Watch is anything but strong. That Stannis threatens to take the land and the castles through force if Jon doesn't willingly give them speaks to this.

It's not so simple as saying the Watch was instituted to guard the realm against the Long Night, and as such, must remain neutral. Pointing out all the times it's said that the Watch must remain neutral doesn't get to the fundamental reason why this was adopted in the first place.

We're told that until very recently, the Watch was, in fact, extremely strong and a comparable power to other kingdoms. Becoming involved in the realm's affairs would have been detrimental, as the Watch acting as an independent political organization against other powers would have imploded it. When the Watch had power in its own right, it could not only afford the luxury of neutrality (it was self-sustained), but neutrality insulated it from attack.

We also know that the Watch, the Umbers and Winterfell were extremely cooperative throughout its history. Specifically, we're told that Winterfell is understood to be the last line of the Watch's defense. That is, Winterfell was the Watch's backup when threats from the North made it past the Wall, and conversely, if unfriendly parties tried attacking the Watch from the South, they'd have to deal with Winterfell. So Winterfell has a role as the enforcer of the Watch's neutrality (and we're told the Umber's were the Stark's frequent allies in this).

Aemon had sent out ravens to all the Northern Houses for aid, and were met with radio silence. Later, Stannis does the same, and is met with the same response (other than Karstark, who's working for the Boltons and Lyanna Mormont who tells Stannis no). So the Watch is not only incredibly weak and has insufficient resources, they were not given any signs that the North would cooperate as was their historical role. Jon knows that the Boltons are the glue that's gumming up the works in the north-- that is, the North can't respond while the Boltons and Freys are holding hostages and have the greatest military strength. And not only that, but even in the event the Bolton's suddenly became invested in the Watch, their strength is clearly needed to keep the fomenting rebellious factions in line. At the start of DwD, there is no one who has a comfortable foot-hold of power in the North, not even the Boltons.

Jon's personal reasons for acting on the Pink Letter aside, I don't see the involvement in Northern politics to be so wholly separated from the "ultimate purpose" of the Watch as I think is being suggested. I think it's far more blurred, and I think appeals to neutrality are too incomplete.

[illrede]

My essays about how GRRM structures his character arcs to give his characters' dilemmas of values. They are not about how x character or y character is awesome and competent. There is much that Jon does that is incredibly brilliant and competent, but it's not my focus here. I must also say that I don't understand the instinct to minimize or sweep away these conflicts of values. They are the heart of the series, as Martin himself has said many times. I in fact did not focus on vow-breaking "hand-wringing" and specifically avoided it, in favor of examining whether Jon's overall conduct re: Stannis was an unwise practical risk to take for the Watch and the larger struggle.

Which of these do you all disagree with:

1. A Stannis victory looked incredibly unlikely at the start of the book, since every Northern family but one had rejected him, the Boltons had 5 times his forces, they knew the terrain better, and beyond them there's the Iron Throne.

Since a Stannis defeat appears the likely outcome, the Lord Commander has the responsibility to affirmatively take measures to try to ensure the Watch can still function and fulfill its greater purpose of defending the realm if that likely outcome in fact happens.

Not only does Jon take no such measures (except the paper shield), but he doesn't even seen to plan for what he will do in the likely event of a Stannis defeat.

The Watch maintaining neutrality in the face of a Bolton victory surely would have been extremely difficult. But there are things Jon could have tried. At the very least he could have sent an emissary to the Boltons to clarify the Watch's policy of neutrality, something he never apparently considers. He also could have taken more affirmative steps to distance himself from Stannis, not let Selyse come to Castle Black, not hang out with Melisandre all the time, etc. There's no guarantee of success, but my point is that Jon doesn't try anything (except the paper shield when his arm is twisted) or even plan for anything, when the outcome is out of his control. Like I said, the Pink Letter being fake doesn't make Jon "right," it means he took a crazy risk and it happened to work out. If the ball happens to bounce his way and Stannis does win (helped by Jon's covert interventions), that doesn't get Jon off the hook for his failure to prepare or plan for the opposite scenario that was always distinctly possible.

Also, if GRRM's point was that it was pointless for Jon to remain neutral, it would have been quite easy for him to throw in a line in an early Reek chapter where a Bolton says, "And after we kill Stannis, we'll murder that Stark bastard at the Wall!" Yet there is nothing to that effect. Instead we get the early warnings that Jon needs to prepare for the possibility of a Stannis loss, and the Pink Letter seemingly vindicating those warnings. Which seems more suggestive of the author's intent, to me.

There isn't a point for "Stannis's success is in the narrow interest of the Night's Watch, and irreplaceably so." That it is such a practically unlikely outcome serves to underline the dire straights the Night's Watch is in where it comes to fulfilling their function. The day of reckoning had come, and found them unfit. Stannis's campaign was the patch.

Jon failing to choose his most optimal disaster is also valid a point for GRRM to make; that he has a path to recapture the historic ideal brings to mind the objection to Satin's appointment as Jon's steward; after cannibalizing the Brothers' existing structure for the leadership cadres that the new garrisons required, Satin ended up in the position because he had a modicum of experience and he could read. Protest was given because the proper candidate for Lord Commander's steward is a young castle-born and castle-educated squire, intended for later leadership positions- there were no known examples of such. If there was one, he had probably been given a castle to command. The protesters ignored that the system had broken and the historic ideal was unachievable in any case; they had a choice of problems. They were deluded.

[Silent Ghost]

I think what also matters is the purpose of the watch. It's purpose is to defend the realm against what lies beyond. In the meantime, the realm entirely destroy's itself from the inside. If Jon doesn't help Stannis, what will be left of the realm won't be worth protecting (in his eyes)

[LordToo-Fat-to-Sit-a-Horse]

great essays.

I think, the neutrality of the NWs is more of a custom than actually part of its vows.

Besides Jon was dealt with losing cards. Given that the NW was in a terrible position and therefore in dire need of assistance, there wasn´t much he could do to distance himself from Stannis (who anyways had the strength to actually take whatever he wanted). I agree he has a personal stake in stannis´s victory, but everything he gave stannis he traded for something else for the NW. Always giving advice behind closed doors. The NW has plausible deniability in whatever dealings they had with the rebel lord.

Being the son of Ned stark, there isn´t much he can do really to avoid others thinking he is aiding Stannis. The lannisters will always think him as Stannis ally, no matter how many "paper shields" he sends.

[Adam Feldman]

It's not so simple as saying the Watch was instituted to guard the realm against the Long Night, and as such, must remain neutral.

That is not at all what I am saying. I listed five good reasons for Jon to back Stannis, including "Stannis is the only king who cares about stopping the Others" and "Jon can win various aid from Stannis that will help him defend the realm."

My critique is not about what the Watch "must" do because of vows or precedent -- it is about the real practical consequences to the Watch in the event of a Lannister/Bolton victory. My point is that, by backing Stannis and doing nothing to prepare or plan for a Bolton win, Jon is choosing to take a risk with the Watch and its ultimate purpose. A risk can redound to the risk-taker's favor. Or it can backfire horribly. I am questioning whether this was a proper risk to take, considering how unlikely the prospect of a Stannis victory seemed at the time.

Now, if Jon literally believes that there is a 100% chance of the Night's Watch being doomed or destroyed in the event of a Lannister/Bolton victory, and that he can do nothing whatsoever to avert this outcome, then it would be a proper risk to take even if Stannis' chances of victory are incredibly small. But let's return to the text here. Jon has many opportunities to think or say this, but he does not:

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. (JON IV)

... “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)

If this was truly Jon's thinking, Martin would have had ample opportunities to write, "The Night's Watch took no part, Jon thought, yet I must support Stannis because it is the only way for me to effectively wage the larger struggle." Martin never does. Jon's thoughts instead indicate a temptation, a rooting interest, and a desire to hope for the best rather than consider the worst -- not a noble dedication to the larger struggle.

There isn't a point for "Stannis's success is in the narrow interest of the Night's Watch, and irreplaceably so."

I object to "irreplaceably." A leader must deal with the world as it is. Jon can help Stannis, but whether Stannis succeeds or fails is ultimately out of his hands. For the purpose of the larger war, Jon has a responsibility to prepare for and plan for a Stannis failure. He does not.

[assjfjgjsgjljljglgjfjsduar]

<snip>

Very well said.

I've said all I needed to say, really. To be honest I've seen more insightful essays on both Jon and Dany on here.

[SeanF]

My essays about how GRRM structures his character arcs to give his characters' dilemmas of values. They are not about how x character or y character is awesome and competent. There is much that Jon does that is incredibly brilliant and competent, but it's not my focus here. I must also say that I don't understand the instinct to minimize or sweep away these conflicts of values. They are the heart of the series, as Martin himself has said many times. I in fact did not focus on vow-breaking "hand-wringing" and specifically avoided it, in favor of examining whether Jon's overall conduct re: Stannis was an unwise practical risk to take for the Watch and the larger struggle.

Which of these do you all disagree with:

1. A Stannis victory looked incredibly unlikely at the start of the book, since every Northern family but one had rejected him, the Boltons had 5 times his forces, they knew the terrain better, and beyond them there's the Iron Throne.

Since a Stannis defeat appears the likely outcome, the Lord Commander has the responsibility to affirmatively take measures to try to ensure the Watch can still function and fulfill its greater purpose of defending the realm if that likely outcome in fact happens.

Not only does Jon take no such measures (except the paper shield), but he doesn't even seen to plan for what he will do in the likely event of a Stannis defeat.

The Watch maintaining neutrality in the face of a Bolton victory surely would have been extremely difficult. But there are things Jon could have tried. At the very least he could have sent an emissary to the Boltons to clarify the Watch's policy of neutrality, something he never apparently considers. He also could have taken more affirmative steps to distance himself from Stannis, not let Selyse come to Castle Black, not hang out with Melisandre all the time, etc. There's no guarantee of success, but my point is that Jon doesn't try anything (except the paper shield when his arm is twisted) or even plan for anything, when the outcome is out of his control. Like I said, the Pink Letter being fake doesn't make Jon "right," it means he took a crazy risk and it happened to work out. If the ball happens to bounce his way and Stannis does win (helped by Jon's covert interventions), that doesn't get Jon off the hook for his failure to prepare or plan for the opposite scenario that was always distinctly possible.

Also, if GRRM's point was that it was pointless for Jon to remain neutral, it would have been quite easy for him to throw in a line in an early Reek chapter where a Bolton says, "And after we kill Stannis, we'll murder that Stark bastard at the Wall!" Yet there is nothing to that effect. Instead we get the early warnings that Jon needs to prepare for the possibility of a Stannis loss, and the Pink Letter seemingly vindicating those warnings. Which seems more suggestive of the author's intent, to me.

Jon's backing Stannis is a gamble - but it's a calculated gamble, and one that he has to take. And, by pointing out how and where Stannis can recruit fresh soldiers, and by integrating wildlings into his own forces, freeing up fresh resources for Stannis, Jon's doing a lot to shift the odds in Stannis' favour.

Stannis is known to be an outstanding commander. Outnumbered 7,500 to 1,500, he can't win. Outnumbered 7,500 to 5,000, he has a good chance.

[Chaircat Meow]

Jon's backing Stannis is a gamble - but it's a calculated gamble, and one that he has to take. And, by pointing out how and where Stannis can recruit fresh soldiers, and by integrating wildlings into his own forces, freeing up fresh resources for Stannis, Jon's doing a lot to shift the odds in Stannis' favour.

Stannis is known to be an outstanding commander. Outnumbered 7,500 to 1,500, he can't win. Outnumbered 7,500 to 5,000, he has a good chance.

Is there any passage in DwD that leads you to believe Jon conceives of his aid to Stannis as connected to the Long Night, and as a necessary gamble?

As Adam Feldman just mentioned in his post, there are a number of occasions where Jon does reflect on what a victory or defeat for Stannis means to him, and the integral nature of that to his efforts to prepare for a zombie invasion is always curiously absent.

This omission is frankly astonishing when you consider there would be no civil war in the north if Jon hadn't saved Stannis from falling into Roose Bolton's trap. Jon has literally ignited a potentially gruelling struggle, at a time when humanity needed to unite, over a hunch wrt the necessity of Stannis, that he never articulates.

Something is very wrong with that.

[Adam Feldman]

This omission is frankly astonishing when you consider there would be no civil war in the north if Jon hadn't saved Stannis from falling into Roose Bolton's trap. Jon has literally ignited a potentially gruelling struggle, at a time when humanity needed to unite, over a hunch wrt the necessity of Stannis, that he never articulates.

Something is very wrong with that.

That is a very good point and I think I will amend the essay to include it. Thank you!

[illrede]

I object to "irreplaceably." A leader must deal with the world as it is. Jon can help Stannis, but whether Stannis succeeds or fails is ultimately out of his hands. For the purpose of the larger war, Jon has a responsibility to prepare for and plan for a Stannis failure. He does not.

I mull over qualifying the extent that Stannis needs to succeed for the Night Watch's purposes (whether he sits the Iron Throne or not is immaterial, and there is a point short of that where his performance simply doesn't matter to their situation), not that that is the path that needs progress. The long term for the Watch has ceased to exist, The Day is here. They really can stop worrying about tomorrow. For that matter, they really should, to the extent that they sacrifice the concerns of today.

So it very well could be that at the point the Pink Letter arrives, Stannis has already fulfilled his necessary utility to the Watch. But at the point Jon Snow became Lord Commander, he hadn't. Between those two points is the Iron Bank loan- the Watch should be observably Stannis-inclined on that day; might as well warn him about the Karstarks then. I won't say that Jon found his optimal disaster, though.

[butterbumps!]

That is not at all what I am saying. I listed five good reasons for Jon to back Stannis, including "Stannis is the only king who cares about stopping the Others" and "Jon can win various aid from Stannis that will help him defend the realm."

I know that's not all you were saying, but it's one aspect I chose to comment on because "neutrality" comes up all the time, and was one facet of your essay I disagreed with.

With regard to Jon's calculus in backing Stannis, the fact that Stannis is the one who calls the Others the "real enemy" was the whole selling point in the first place back in aSoS. Stannis names it as the same war in Jon XI, and their subsequent DwD strategy discussions are about the pragmatics of this. From the time of Stannis' offer, it's clear that Jon sees Stannis as aligned with the original purpose of the NW, and is his proxy to sort out the North in order for that to happen.

[Adam Feldman]

Very well said.

I've said all I needed to say, really. To be honest I've seen more insightful essays on both Jon and Dany on here.

Well you haven't said much, but you've certainly made your snide disdain very clear! I suppose I will be left in suspense as to whether you think (1) Stannis' chances of success at the outset were quite low, and (2) As LC, Jon had the responsibility to plan for and prepare for the very real possibility that Stannis would lose.

[SeanF]

Is there any passage in DwD that leads you to believe Jon conceives of his aid to Stannis as connected to the Long Night, and as a necessary gamble?

As Adam Feldman just mentioned in his post, there are a number of occasions where Jon does reflect on what a victory or defeat for Stannis means to him, and the integral nature of that to his efforts to prepare for a zombie invasion is always curiously absent.

This omission is frankly astonishing when you consider there would be no civil war in the north if Jon hadn't saved Stannis from falling into Roose Bolton's trap. Jon has literally ignited a potentially gruelling struggle, at a time when humanity needed to unite, over a hunch wrt the necessity of Stannis, that he never articulates.

Something is very wrong with that.

With or without Stannis, we know that civil war would break out in the North. Even on his own, Manderly is powerful enough to challenge Roose Bolton.

[butterbumps!]

Well you haven't said much, but you've certainly made your snide disdain very clear! I suppose I will be left in suspense as to whether you think (1) Stannis' chances of success at the outset were quite low, and (2) As LC, Jon had the responsibility to plan for and prepare for the very real possibility that Stannis would lose.

Jon I is when a smaller strategy session occurs, but Jon's major strategy session with Stannis happens in Jon IV, DwD. News of Tywin's death reaches them in Jon III, and he understands that this means Stannis' success is very likely. So by the time Jon is offering the significant strategic aid to and investment in Stannis in Jon IV, Tywin's death is known, which undermines both Lannister and Bolton power, rendering Stannis' chances much higher.

[Chaircat Meow]

With or without Stannis, we know that civil war would break out in the North. Even on his own, Manderly is powerful enough to challenge Roose Bolton.

Actually no, given Manderly was only free to move because Davos found his way to White Harbour (his fake execution convinced Cersei to release his son).

Jon doesn't know this either, so it's all irrelevant.

[LordToo-Fat-to-Sit-a-Horse]

Jon might have known that in the event of Stannis defeat, he always had the option of doing exactly what he did at the end of ADWD. Distance himself from the NW to save it. Marching south, alone (to explain his actions and die), or with his wildling friends with some chance of winning against Ramsay. Either way the NW is effectively separated from his actions. The lannisters and Bolton might want him dead, once they have his head, the NW will be safe..

I think the one true mistake that Jon did, was never grooming a replacement that can keep the alliance with the free folk going. It really doesn´t matter how many paper shields, or gestures he does to separate himself from Stannis, at least in the eyes of Bolton/lannister. At the end, he should have known that if Stannis was a losing bet, the best way to save the NW was paying with his life. In that case, keeping the alliance with the free folk was paramount to the safety of the realm.

[LordToo-Fat-to-Sit-a-Horse]

With or without Stannis, we know that civil war would break out in the North. Even on his own, Manderly is powerful enough to challenge Roose Bolton.

*We* know that civil war ...As readers we know about Manderly treachery.

What matters in these essays is Jon´s POV. Jon knows Manderly has rejected on numerous times Stannis offers.

[Adam Feldman]

Jon I is when a smaller strategy session occurs, but Jon's major strategy session with Stannis happens in Jon IV, DwD. News of Tywin's death reaches them in Jon III, and he understands that this means Stannis' success is very likely. So by the time Jon is offering the significant strategic aid to and investment in Stannis in Jon IV, Tywin's death is known, which undermines both Lannister and Bolton power, rendering Stannis' chances much higher.

Tywin's death is surely important. But there is a countervailing event -- in Jon II, Jon tells Sam that raising White Harbor is crucial to Stannis' success, and in Jon IV, Stannis says he has had no word from White Harbor, that Davos may have died on the way, and that he can't wait for them anymore.

I think the one true mistake that Jon did, was never grooming a replacement that can keep the alliance with the free folk going. It really doesn´t matter how many paper shields, or gestures he does to separate himself from Stannis, at least in the eyes of Bolton/lannister. At the end, he should have known that if Stannis was a losing bet, the best way to save the NW was paying with his life. In that case, keeping the alliance with the free folk was paramount to the safety of the realm.

Yes, this is another form of contingency planning that Jon could have done to prepare for a possible Bolton victory, but did not do.