On House of the Dragon, Alicent Hightower's brother Gwayne's story has so far been that of the rational, straight man sidekick to the egotistical Hand of the King, Ser Criston Cole. Their rapid campaign through the Crownlands in season 2 led them to two victories at Duskendale and the pyrrhic victory at Rook's Rest. The horrors of Rook's Rest laid bare to these men how little of their lives they actually controlled, something that will likely play a more integral factor in Gwayne's character development in the upcoming third season.
Beware SPOILERS for House of the Dragon from here on out
House of the Dragon is based on the book Fire & Blood by George R.R. Martin, where Gwayne's story plays out a bit differently. At this point in the story in the book, Gwayne is in King's Landing, and is there when Rhaenyra Targaryen takes over and sits the Iron Throne. He serves as the second-in-command of the Goldcloaks, tasked with spying on their commander, Ser Luthor Largent, a suspected Black sympathiser. During the fall of King's Landing, he is ultimately killed by Largent after he's arrested during Rhaenyra's coup d'etat. But on House of the Dragon, Gwayne is on his way to Harrenhal with Ser Criston Cole.
The Greens recapturing Harrenhal will mark a significant moment in the war, not because of the incident itself, but because of what happens over the following days, as Criston Cole, Aemond Targaryen, and (now) Gwayne Hightower deliberate their next course of action.
Aemond Targaryen is already acting as Prince Regent. With the news of King's Landings' fall to the Blacks and the disappearance of his brother King Aegon, Aemond's ego will likely go into overdrive, since in his brother's absence it is even more clear that he is the leader of the Greens. This, I believe, will ultimately be to the detriment of his and Ser Criston's seemingly close relationship, as the latter is currently undergoing an existential crisis and arguably not in any mind to fight a civil war.
Gwayne, as the most rational man in the room, will likely try to act as the diplomat between Aemond and Criston, tempering the worst aspects of their characters. However, I fear it will be a futile attempt, as Fire & Blood readers will know that Aemond and Ser Criston ultimately part ways. The specific reason for this remains somewhat of a mystery and could revolve around a number of factors. For instance, Aemond's obsession with Alys Rivers will likely be far stronger than Daemon's, as he craves to be loved and to be listened to, only ever having gotten that from the prostitute Sylvi. Alys Rivers' intriguing personality will captivate Aemond. In Fire & Blood, after finding out the King's Landing has fallen, Aemond treats Harrenhal castellan Ser Simon Strong very cruelly. That will likely sew division between him and his commanders. They also might split up just because it makes more military sense.
But whatever the reason for Aemond and Criston going their separate ways, I believe that Gwayne will go with Criston, who may have a semi-redemption arc in season 3 leading to his tragic and undignified end.
If the show follows the book, Criston's fate will be decided at the event known as the Butcher's Ball. More of a massacre than a battle, Criston's exhausted army are surrounded by Rhaenyra's Riverlands allies and the Winter Wolves, the Northern soldiers who crossed south at the end of season 2. I like to think that, in understanding his fate, Criston will thank Ser Gwayne for helping him to see clearly again. Several conversations between the two men could take place up until this point where Gwayne is trying to restore some sense and clarity back to his commander, whether it be for his sake, or for the hundreds of men under his command. Criston will likely give his final order for Gwayne to inform Prince Daeron and Lord Ormund Hightower what happened to him. Gwayne, despite some reluctance, will ultimately oblige and manage to escape the Butcher's Ball.
Following these events, Gwayne will link up with his nephew, Daeron Targaryen, probably in the aftermath of the First Battle of Tumbleton. It is at this point where the character of Gwayne Hightower will merge with another member of House Hightower: Hobert.
Ser Hobert Hightower is an elderly, distant relative of Gwayne. His role is very much a minor one in the early stages of the Dance of the Dragons, commanding the Hightower baggage train. However, in the immediate aftermath of Lord Ormund Hightower's death, his family name means he becomes a major contender to lead the army.
Hobert Hightower was already played by Steffan Rhodri in the first season of House of the Dragon. But I believe that these two Hightowers will become the same character in season 3, at least in terms of their narrative functions. If one looks a little deeper to Gwayne's current trajectory, it seems very plausible that he could end up turning to alcohol. After all, by this point in the story, he's seen the devastation of the dragons at Rook's Rest, his sister Alicent is imprisoned, his nephew Maelor (if he exists on the show) has been cruelly murdered, Ormund has been killed in battle and Criston (who could potentially be counted as a friend if their relationship develops in the way I think it will) is dead. Why wouldn't Gwayne turn to drink after having lost so many friends and family members? In Fire & Blood, the detail of Hobert being a drinker becomes crucial when he (or Gwayne, in House of the Dragon) attempt to rid the Greens of one of the treacherous Dragonseeds, namely Ulf White. But that is a story for season 4 (most likely).
This, I believe, will be Gwayne's story for House of the Dragon season 3, and I look forward to seeing actor Freddie Fox take up the Green cause once again.
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