This is not a silly question!

What Littlefinger has done with Nestor Royce - and I think he, Baelish, very much understands it - is handed Nestor a sort of dynastic white elephant, useful to Nestor and his branch of the family in the short term but potentially, and deceptively, politically tricky to hold long term. As Nestor notes to Baelish, “even after [the Targaryen Conquest], the Gates remained an Arryn castle”, a seat by some reckoning “as royal as the Eyrie”. Yet as both Nestor and Littlefinger acknowledge, even if the position of Keeper had never been hereditary, its officeholders had almost exclusively hailed from House Arryn: Nestor recalls that “Jon Arryn himself was Keeper of the Gates whilst his father lived” and as lord “named his brother Ronnel to the honor, and later his cousin Denys”, while Baelish explains to Sansa that “Lysa dreamed of other sons and meant the castle to go to Robert’s little brother”. Littlefinger blithely dismisses Nestor’s response by saying that “Lord Robert has no brothers, and only distant cousins”, but the point remains: Littlefinger has given Nestor and his family a seat that by every reckoning has always belonged to, and remained with, the Royces’ Arryn overlords.

Baelish’s grant, then, represents a substantial breaking of quite literally centuries of Arryn tradition - not merely investing the keeping of the castle in a non-Arryn (as even Lord Jon felt prepared to do when he lacked an adult male Arryn relative for the post), but formally naming that keeper the hereditary lord of this very Arryn castle. Indeed, Nestor Royce seems aware of the worryingly unprecedented nature of the grant, remarking that Littlefinger was “not without courage” to order as much, since “[s]ome will call this grant unseemly, and fault [him] for making it”. If Littlefinger is technically correct that young Robert lacks brothers or (patrilineal Arryn) cousins who might have expected to take over the position of Keeper, he has limited the observation to this generation of House Arryn. Littlefinger is keenly aware that the future of House Arryn - at least as he, Littlefinger, has planned it - will rest not with the young lord Littlefinger is actively poisoning but the Hardyng cousin whose betrothal to his own “daughter” Littlefinger has arranged by the end of AFFC. In some far-off potential future for House Arryn, would Harry and Sansa’s sons or grandsons or other descendants appreciate that their ancestral castle, the first foothold of the family in the Vale, was held in lordship, rather than merely stewardship, not by House Arryn but by a secondary branch of the Royces? In some future era of tension within the Vale, could the Royces of the Gates of the Moon keep a Lord or Lady Arryn as a virtual hostage of the castle, or even trap their overlords on the Giant’s Lance? The recent experience of the almost-siege of the Lords Declarant, as well as the similar actions taken by Lord Allard Royce against the usurping Jonos Arryn in the first century AC, illustrate how the Gates of the Moon could function during geopolitical strife in the Vale. As hereditary keepers of the Gates of the Moon, the Royces might find themselves the unwelcome landlords of their liege-tenants.

Of course, Littlefinger does not care what fallout the Royces might ever experience in the future. Baelish obtained what he wanted out of the deal - the invaluable thanks of, and subsequently an alliance with, a blue-blooded Vale aristocrat - at a cheap price; again, with no Arryn brothers or male-line cousins around, and with Baelish himself as Lord Protector of the Vale, Littlefinger could pass on the Gates of the Moon without an obvious source of challenge. More to the point, Littlefinger is expecting to get out of the Vale sooner rather than later, with Sansa and Harry leading an army of Vale chivalry to claim Winterfell in her name. Even if Nestor Royce comes along (and he might, not only as a highborn aristocrat but also as the vehicle for his highly intriguing daughter), the Gates debate will hardly demand as much attention in a struggle of third-party Stark factionalism.

It is almost impossible to say with either Loron or Alton Greyjoy, of course. While TWOIAF suggests that both were post-Conquest Lords of the Iron Islands, the sole paragraph that mentions them does not appear to list them in any sort of obviously chronological order. Nor does the lack of detail on the Iron Islands generally or the Greyjoys specifically for huge swathes of Fire and Blood Volume 1 help us here: in the same way that there is little basis for speculation on what geopolitically drove the ironborn delegation at the Great Council of 101 AC, so there is little to say about when any of these men (other than Dagon, and to a somewhat lesser extent Torwyn) lived.

However, I will say I enjoy the headcanon that Alton Greyjoy was the father of Dagon Greyjoy. The “Holy Fool” who “sought new lands to conquer beyond the Lonely Light” may serve as an intriguing contrast to Dagon “the Last Reaver”. Of course, given that according to GRRM “[n]o one has ever crossed the Sunset Sea to learn what lies on the other side” (the mystery of Elissa Farman’s ultimate fate notwithstanding), as well as the sheer distance even between the Lonely Light and the rest of the Iron Islands, I highly doubt that Lord Alton did in fact find those “new lands to conquer”, much less brought any such lands under the Greyjoy banner. Likewise, given Alton’s epithet as a “fool” (albeit a “holy” one), it is possible that Alton’s memory on the Iron Islands is far from a positive one: a man seemingly so dedicated to the expansion of the Drowned God’s worship and the continued domination of the Drowned God’s chosen race (that is, the ironborn) that he would sail even beyond the domains of those “queer folk” on the Lonely Light, into waters unfamiliar even for Greyjoy ships. (Compare, say, Euron’s belated, somewhat mocking acknowledgment at the kingsmoot that he would lead the conquest of Westeros “[a]ll for the greater glory of our Drowned God, to be sure”.)

(I would wonder to what extent GRRM is aware of the real-world concept of the “holy fool”, but that’s really beyond the scope of this post.)

If Alton was in fact Dagon’s father, then perhaps Dagon’s reaving and terror along the west coast were in part a response to what appears to have been his father’s failed dreams of conquest. The destiny of the ironborn, so Dagon may have decided, was not to rush foolishly into the unknown west but to revive the Old Way imperialism of the Westerosi west coast at its height during the reign of the Hoare kings. To make up, perhaps, for what he may have seen as his father’s inability to pursue an ironborn empire in or beyond the Sunset Sea, Dagon may have thought to subjugate the mainland Westerosi who were so much closer to hand.

My best guess (and this is only a guess) is that Lyonel “the Laughing Storm” and Gowen Baratheon were the first and third sons of an unnamed Lord Baratheon, born in the late second century AC. Lyonel Baratheon, I believe, may have married and had a son in about 200 AC, when he, Lyonel, would have been about in his late teens or early to mid 20s - perfectly old enough by Westerosi standards for the heir of an aristocratic family to have married and fathered a child. Because this boy would have been the second in line, after his own father, to Storm’s End, Lord Baratheon then perhaps decided to host a hastilude in his new grandson’s honor, at which Prince Baelor tilted against Ser Arlan of Pennytree. Gowen Baratheon then married Tya Lannister circa 208 AC (in a relatively rare, but not completely unprecedented, example of inter-kingdom marriage in Westeros). At some point in the aftermath of the tourney of Ashford, Lyonel and Gowen’s father died and Lyonel became the new Lord of Storm’s End.

Meanwhile, Lyonel had at least one other child - the daughter betrothed to Prince Duncan Targaryen. While it might seem a bit tough for Duncan’s fiancée to be a sister of a Baratheon son born circa 200 AC - since Prince Duncan himself was born between 220 and 224 AC - I think there is enough room to fudge a believable gap for marriage between the two, especially if the Baratheon daughter was a few years older than her royal fiancé. (After all, Robert Baratheon was some 15 years older than his brother Renly, for example, to say nothing of the distance between Rhaegar and his surviving brother and sister.)

At some point, perhaps in about the late 210s or early 220s AC, Lyonel’s unnamed (possible) son married (a similarly unidentifiable woman, though more likely than not a Stormlands aristocrat). Lyonel’s son then, maybe, had his own son, Ormund, perhaps around the mid to late 220s AC (to be of an age with his eventual wife, Princess Rhaelle). This, I think, may have been the stability enjoyed by House Baratheon that made Lord Lyonel content to betroth his daughter to Egg’s own heir. He, Lyonel, had at least one son and a grandson, just as his own father had had when Papa Baratheon hosted that hastilude and married off brother Gowen to a Lannister; the Baratheon dynasty could extend itself in such a prestigious marriage arrangement.

Then, in 239 AC, the Baratheon dynasty received the bombshell news that Prince Duncan had married Jenny of Oldstones. Lyonel, of course renounced his fealty to the Iron Throne and had himself proclaimed a new Storm King - and if he did in fact have a nearly 40 year old son, I could see this son joining his father in rebellion against the Targaryens. How much more poignant, then, if Lyonel’s son died during his father’s “short, bloody rebellion”, leaving his son Ormund as Lyonel’s new heir. Both Lyonel and Aegon V would have lost their eldest sons and heirs in the course of the conflict - Aegon politically, after Prince Duncan abdicated as Prince of Dragonstone, and Lyonel of course far more permanently. I could see GRRM using the death of this (possible) Baratheon son as a statement on the futility of war and the seemingly endless cycle of violent vengeance, both favorite themes of his throughout ASOIAF: did Lyonel’s son have to die to satisfy the pride and honor of House Baratheon, which Prince Duncan had insulted, and how many Targaryen and Baratheon men both would then have to die to avenge the life of the late heir? Too, how much grief would Egg have felt not only that his own son had forsaken his royal inheritance to marry a commoner, but also that Duncan’s decision led to war with his old ally and supporter Lord Lyonel, a war which may have seen Lyonel lose his son in turn? This is speculation on top of speculation, but it feels like the sort of rich narrative GRRM may play with in a future entry in the Tales of Dunk and Egg.

I see Renly’s childhood, especially after Robert’s Rebellion, as being perhaps vaguely similar to Bran’s period as heir presumptive to Winterfell following Robb’s acclamation as king. Like Bran, who at eight years old acted in Robb’s place as Lord of Winterfell during ACOK, Renly became Lord of Storm’s End (albeit in his own right) when he was about eight or nine years old. However, just as no one truly expected Bran to rule on his own as acting Lord of Winterfell at this time, so I doubt Renly was expected to take on many responsibilities as Lord of Storm’s End through his childhood until his majority. In turn, just as Winterfell’s affairs were overseen by a sort of two-person regency comprised in Rodrik Cassel and Maester Luwin, so I imagine Storm’s End and the Stormlands were in practice governed by members of young Renly’s household.

The composition of that household is an open question, of course. It is possible Cortnay Penrose filled some role in governing Storm’s End in Renly’s childhood: we do not have a sense of when Cortnay joined the household, but his bald and weathered face certainly suggests an older man, his position would have been aristocratic enough, and his fondness for young Edric Storm now may indicate he once showed a similar fondness for young Renly. However, it is entirely possible that Renly’s household in his minority was ruled by characters we have never met (and likely will never meet); Corttnay Pernose was certainly not the only aristocrat who ever served Storm’s End. We do not know, for example, who replaced Cressen as maester of the castle (at least until Maester Jurne began service), and given the traditional maesterly role as both tutors to noble children and advisors to the heads of households, I could see Storm’s End maester serving in a quasi-paternal as well as regent role for young Renly. We have even less to say about, for example, the master-at-arms of the castle in Renly’s childhood, or the castellan (more on that in a moment), or any other Baratheon household officer who might have helped raise Renly. (It’s probably redundant to say that there is nothing to say of any women who might have had a hand in Renly’s upbringing, either.)

I will say, though, that it is possible Renly’s childhood household included relatives, if not immediate family members. Stannis remembers a Ser Harbert, whom he describes as a great-uncle, as castellan of Storm’s End when he, Stannis, was young; while it is unclear if this great-uncle was still alive when Renly was growing up (as he was already “old Ser Harbert” when Patchface washed ashore), Renly may have known this great-uncle in his youth. Too, while they would not necessarily have been members of the Storm’s End household (beyond the father and husband of the Estermont widow Robert slept with on Greenstone), the Estermonts were certainly close with the Baratheons of Robert’s (and consequently Renly’s) generation; it is possible that, as much as Robert played with Estermonts as a child and wished to visit his kin during his reign, Renly may have grown up regarding the Estermonts as family. It is possible that one or more of these relatives might have served in some regency capacity for young Renly.

It is too difficult to say what was in Renly’s mind in these years. However, I do not think it too great a leap to suggest that Renly saw the grand Tyrell army, feasting while he starved with distant brother Stannis inside their castle, and felt longing instead of hatred. Likewise, it’s reasonable to see Renly as a boy inside the vastness of Storm’s End, head of the House but largely if not entirely bereft of relatives or loved ones - until both the Tyrells and love came into (or back into) his life with Loras.

On the one hand, I am not sure how long Myriah’s training as heiress to Dorne continued in her childhood relative to her betrothal to then-Prince Daeron. Baelor and the unnamed Prince of Dorne agreed to the betrothal when both Daeron and Myriah were children; Daeron was about eight, but we do not have an idea of exactly how old Myriah was. If the Prince of Dorne truly disinherited Myriah as heiress to Sunspear as part of or in consequence of this betrothal, then it is possible that Myriah’s education and training shifted from preparation for ruling Dorne to preparation for becoming a Targaryen bride. Myriah and Daeron were married by 170 AC (the year the future Baelor Breakspear was born), so Myriah may have had about or up to nine years of knowing that she would marry a foreign (in Martell eyes) prince and live in the Targaryen kingdom, never to rule in Sunspear.

Of course, we do not know what Myriah knew or believed of her betrothal and future, and how she might have been educated accordingly. Was Myriah aware for that period that she would eventually marry Prince Daeron, or did the Prince of Dorne keep the betrothal secret for any amount of time (more on that below)? To the extent that Myriah did not know or was not made aware that her fiancé was a cousin of the Targaryen king, did she view herself and/or was she educated in the context of her future marriage? We see via Arianne in AFFC a Martell princess and would-be heiress to Dorne left in ignorance of her Targaryen betrothal, only aware that she had been given little in the way of formal authority and that her younger brother had been favored by their father to inherit. Myriah does not have to parallel Arianne exactly (or at all), but it is interesting to speculate whether Myriah came to her Targaryen marriage deeply imbued with a sense of her former Dornish inheritance (as, incidentally, I believe Arianne will, as heiress to Dorne, in marrying Aegon).

Nor indeed do we have a clear idea of how Sunspear viewed the Iron Throne in the perhaps better part of a decade between Baelor’s peace negotiation and the wedding of Daeron and Myriah. While I certainly believe the Prince of Dorne may have welcomed Baelor’s complete reversal of the Young Dragon’s campaigns of conquest, at the same time the Prince of Dorne may have worried about how long this new pious king would last. Baelor had undertaken a hugely physically exhausting task merely in walking to Sunspear, and though the Prince would not have known at the time of the betrothal, Baelor would nearly die during his return to King’s Landing following the rescue of Prince Aemon. Any news of Baelor’s fasts may have deepened the Prince’s worry: Baelor’s death while Myriah and Daeron were still in their minority might have called into question whatever succession plan Baelor had made, and by extension whether Myriah and Daeron would wed. Too, it would do no good for Sunspear to commit itself publicly to a Targaryen-Martell union, especially in the immediate aftermath of the Young Dragon’s violence and bloodshed, if Baelor’s reign appeared too unstable, or if the hawks (dragons?) of Daeron I’s government tried to take over setting policy. In turn, we can only guess how the Prince of Dorne approached the education of his oldest child as a future Targaryen bride versus as his heir.

However, whatever training or education Myriah had received as onetime heiress to Dorne, I do not want to discount the influence of Myriah Martell on Daeron II’s rule and regnal policies. Whether or not Myriah approached her eventual queenship with the lessons of her time as heiress to Dorne, she certainly extended some leverage over her husband’s court: Yandel notes that “Daeron II brought many Dornishmen to his court, some of whom were granted offices of note” and that “some questioned the influence of his Dornish wife” during his reign. We have too little sense - indeed, almost none at all - about Myriah as a character, and so little room to understand to what extent Daeron II’s pro-Dorne policies were as a result of her presence and advice, versus his politico-personal mutual antagonism with his vehemently anti-Dorne father, or his admiration for the vigorously pro-peace Baelor the Blessed (all of which factors are, of course, interrelated and none of which are mutually exclusive). I think it is fair enough to say that Myriah had received at least as good of an education as any very highly born Westerosi aristocratic girl (especially one expected eventually to marry a foreign prince), and perhaps better for as long as she was officially heir to Dorne, and that she had every reason, as the daughter and sister of reigning Martell princes as much as the onetime heir herself, to favor, promote, and advocate for Dornishmen and women at court, align herself with her husband’s peace policies, and support unification between Dorne and the Iron Throne’s kingdom.

Absolutely not. From the moment Alicent gave birth to her sons, the queen and the green faction wanted Aegon and his brothers to succeed their father ahead of Rhaenyra. Years before Jacaerys was born, Alicent and her father were lobbying Viserys to change his decision on the succession - so much so that Viserys sacked Ser Otto as Hand in 109 AC, five years before Jacaerys’ birth, with the declaration that Lyonel Strong, his new Hand, “[would] not hector [him]”. Gyldayn had already identified the “queen’s party” and the “party of the princess” as extant following Otto Hightower’s termination, and named them with their familiar color designations as of the tourney of 111 AC. For two decades, these parties deepened their mutual antagonism: the Iron Throne was a zero sum game, its seat only big enough for either Aegon or Rhaenyra alone. If the polite and very transitory fiction of the king’s loveday could not change that reality, no amount of cross-factional marriages would either.

Too, such a marriage between Jacaerys and Helaena would require the green faction to acknowledge the legitimacy of the former - a point the green faction, consistently, vehemently, and violently denied. Gyldayn repeats not only Alicent’s sniping comment to Laenor after Lucerys’ birth - that if he, Laenor, kept having children with Rhaenyra, “soon or late, you may get one who looks like you” - but also the “article of faith” amongst the greens that “the father of Rhaenyra’s sons was not her husband, Laenor, but her champion, Harwin Strong”. Alicent’s sons had certainly learned by 120 AC to denounce Rhaenyra’s sons as “Strongs”, with Aegon merely shrugging that “[e]veryone [sic] kn[ew]” about the boys’ extramarital origins just to look at them. No matter how true the accusation probably was, and no matter how firmly Viserys attempted to shut down this particular line of questioning, the green faction was never going to agree to a marriage between Alicent’s only daughter and an ostensibly Velaryon prince the greens held to be a bastard.

Indeed, what we see of the marriages and betrothals among the children of these factions IOTL was a desire not to merge these groups together but to emphasize mutual isolation from each rival faction. Alicent may have contemplated marriage between her Aegon and Rhaenyra (less a goodwill gesture to the latter and more, I think, a guarantee of Aegon’s accession and reliance on patriarchal expectations to promote him eventually as sole ruler), but when Viserys shut down that idea, Alicent’s solution was to marry Aegon to Helaena - another way of emphasizing Aegon’s role as heir to the similarly incestuously married Conqueror (and, by extension, Aegon’s right to take the Conqueror’s throne). Rhaenyra, for her part, betrothed her eldest sons when the boys were little more than toddlers - early even by Westerosi standards, and a clear indication both that Rhaenyra had aligned herself with the Velaryon-Targaryen branch of the family and that her sons were not available for the nuptial schemes of either the green faction or the king (since Rhaenyra firmly held out her sons as Velaryons, nevermind the antipathy of the greens as I mentioned). Far from either faction being willing to use the traditional tool of dynastic marriage to make peace, both the blacks and the greens dug themselves in more deeply to their positions in the decade before the Dance.

This got long, more under the cut:

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We do not get really any sense of these families during Viserys I’s reign or at the outset of the Dance, so it is fundamentally impossible to say. However, what I personally headcanon, and I think makes as much sense as any other explanation, is the idea that these families attempted on a somewhat more local scale what families like the Yronwoods, the Reynes, and the Sunderlands may have attempted during the First Blackfyre Rebellion. As the late great Steven Attewell once speculated, these families and others may have rallied to Daemon Blackfyre because a Blackfyre victory offered more opportunity for advancement than did a loyalist victory. If Daemon Blackfyre emerged triumphant, the new Blackfyre government may well have decided either to depose or to severely humble those families who supported the Targaryens - and who better to profit from that decision than disgruntled pro-Blackfyre vassals of those great Houses?

Similarly, the Costaynes and Mullendores may have decided that if there were ever a time to try to challenge the might of the Hightower, the Dance was perfect chance to do so. On their own, the Mullendores and Costaynes would never have the strength to rebel, at least successfully, against House Hightower, one of the richest and mightiest families not just of the Reach but of the entire realm. However, by joining a national civil war on the side defying the Hightowers, the Costaynes and Mullendores may have believed they were well-positioned to be rewarded if the black faction triumphed. Whether or not Rhaenyra’s government, had it ultimately emerged victorious, would have ordered a complete damnatio memoriae against House Hightower, it is very possible if not probable that the Hightowers would have lost at least some lands and wealth (as did, say, the Blackwoods in the aftermath of the Red Wedding, or more extremely the Conningtons after Robert’s Rebellion). As pro-black Hightower vassals, the Mullendores and Costaynes may have expected to receive some of this redistribution (along with, perhaps, their Tarly neighbors).

I think there are a few points to be noted here.

Number one, I believe Selwyn Tarth did attempt to choose a husband for his daughter who, in Selwyn’s mind (and personalities very much aside), would have been a realistic marriage choice. As the head of an ancient and high-ranking family, Selwyn certainly knew that any husband for Brienne would have needed to be blue-blooded enough to serve as a consort to the Lady of Tarth (and, perhaps, jure uxoris lord himself). At the same time, Selwyn likely would have avoid too powerful a potential son-in-law, whose marriage to Brienne might mean that Tarth would become a mere satellite of her husband’s own holding. Brienne’s childhood fiancé, the second son of Lord Bryce Caron, likely would have fit the bill (again, speaking in purely political terms): the son of a similarly blue-blooded Stormlands family, yet not directly heir to Nightsong. Likewise, Ronnet Connington might have appeared on paper to enjoy the dynastic credentials required for a Tarth husband while being sufficiently humbled by the Connington losses during Robert’s Rebellion not to overshadow his bride. There is less to say about Humfrey Wagstaff (given his surname seems to be mostly a priapic joke), but I think it is fair to assume that, given his knighthood and position as Grandview’s castellan, Ser Humfrey was at least considered well-bred enough to be a husband to Brienne. In sum, Selwyn Tarth in-text knew the sort of dynastically appropriate suitor to seek out for his heiress; the failure of any these betrothals to result in a marriage was a combination of circumstantial bad luck and wildly incompatible (and deeply deplorable, on the part of the men in question) personalities.

More importantly, once it became clear that Brienne both wanted martial training and would not give it up after any marriage she might undertake, Selwyn specifically refused to press the point. Selwyn might well have tried to force Brienne into any marriage simply with the aim of producing a (male) heir of his line, or might have remarried himself to father a son who could replace her in the Tarth succession, or might have promoted a Tarth kinsman as a would-be alternate heir (as Wyman Webber did, to Rohanne’s chagrin). That Selwyn took none of these actions speaks to a desire, at bare minimum, not to pursue a marriage for his daughter or to secure the male future of House Tarth above all other considerations, including his daughter’s wants. Selwyn was (and is) probably intelligent enough to understand, as Ser Humfrey and Red Ronnet made very obvious, that few if any Westerosi male aristocrats would view Brienne’s outward appearance and fighting ability without derision and disdain - and that those who would, like Hyle Hunt, would likely be poor minor noblemen with an interest in her substantial landed inheritance, not her person.

On top of all of that, Brienne herself certainly showed no romantic or personal interest before the events of the novels in anyone but Renly Baratheon. Whether or not Selwyn even knew about her infatuation with Renly (or Renly’s own sexuality, which seems to have been something of an open secret), I doubt that Selwyn thought it likely that the king’s brother and Lord of Storm’s End in his own right would marry his own vassal’s heiress, even without her being considered ugly by the standards of Westeros. With Selwyn apparently unconcerned about Brienne’s unmarried state, and Brienne herself not showing a great interest (at least to Selwyn’s probable knowledge) in anyone but Renly, I’m not sure there is more Selwyn could or would have done without completely changing his and/or Brienne’s personalities.