If Jaehaerys and Shaera had married their various betrotheds only for their spouses to die without issue, could they have married each other without harming Aegon’s political agenda (eskewing the incest)?

They would still harm it in a way but in the sense of not advancing it rather than incurring the anger of two Great Houses as they did in OTL. This scenario might spare Aegon the wrath of Houses Tyrell and Tully*, but it also does nothing to support his political reforms. Aegon relied on marital and future blood relations with the great houses to aid him in passing his reforms, but if by some stroke of extremely bad luck, both Luthor Tyrell and Celia Tully die without issue, the marriages would not have served his purposes since those alliances would be all but dead. All that would tie the crown to those houses at this point is mutual regard, and little more. Perhaps he might hope to count on whatever personal relationships Jaehaerys and Shaera might have cultivated with their late spouses’ families while the marriages lasted but that’s not an assured source of support. Which is why Aegon would want to make other dynastic matches for his children (Jon Arryn, for example, for Shaera, and Olenna Redwyne for Jaehaerys to make up for the broken betrothal with Daeron) so he could count on lordly support for his reforms.

(*I say might because neither Jaehaerys or Shaera was exactly the soul of
responsibility and duty. I can see them following the model of Rhaenyra
and Daemon the Rogue Prince and not waiting an appropriate amount of
time after the death of their spouses to get married if they anticipate that Aegon would look to other dynastic matches and look to forestall that by presenting their marriage as a fait accompli as they did in OTL. Needless to say, that would not sit very well with the
Tyrells and the Tullys, and might even give life to rumors of a previous affair
between the siblings.

)

i had a thought – in the au where jon arryn dies before he and lysa have a kid, would a willas tyrell match be possible? say this is post-crippling. would a widow of a paramount house be acceptable for a disabled heir of a paramount house be an acceptable match even if the widow is older than the heir (say, like five years)

The acceptability of any given match is completely situational so I can not speak in broader terms here. But in the case of Willas-Lysa, I’d have to say no. This match might not be without advantageous in that a union with a Tully would get Mace into the alliance bloc that put Robert on the throne instead of the shaky ground he was on with the current royal House

post-rebellion for having fought for the Targaryens (symbolized by the Stannis-Selyse match that served as a warning to the Tyrells), but Mace and Olenna are way too ambitious and politically savvy to go with this match. Willas is their greatest marital pawn, one that we’ve seen Mace very careful with giving away so that he could score the most profitable match possible. But while they were a part of the victorious rebel coalition, the Tullys may not altogether be ample enough for the Lord of Highgarden to award his heir to. For one, they are the most distant from Robert’s person within the coalition in a political model where proximity to the king is an avenue to power. Lysa’s widowhood would hardly give her any advantage as well since it actually limits the Tully’s access to Robert even further by removing Lysa from the capital. By Jon Arryn’s death, the Tullys’ connection to Robert would be limited to being through Ned, but while being kin to the king’s beloved foster brother might not be a bad dynastic decision for some houses, the worth of even that connection diminishes significantly with Ned sequestering himself in the North away from southern politics instead of staying in King’s Landing and reaping the rewards of his proximity to the king. So a match to Lysa would involve the Tyrells giving away their most valuable marital prize to an older widow for extremely limited profit and virtually no additional power or place in the new Baratheon government, effectively squandering Willas’ hand. Why would the Tyrells do that when they can score a nice alliance with the young Lord of Storm’s End that allows them a much better access to Robert without having to waste any valuable marital prize?

Of course, there’s also the matter of Lysa’s fertility which would come into question the more she ages and the longer she stays married to Jon without producing an heir. Lysa suffered from multiple miscarriages and stillbirths throughout her marriage to Jon so the longer Jon lives, the more Lysa’s childbearing problems become notable. With limited political gain, the age difference between Lysa and Willas, and her ability to bear living children being in question, this match looks very poor indeed from the Tyrell perspective.

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