Is it possible for a Riverlander King to win the Great Game, or at least dominate it for an extended eriod ?

I think anything’s possible, and certainly there have been periods of stronger and weaker Kingdoms of the Rivers and Hills

I think a couple different things would be necessary for a Riverlander King to become dominant:

  • economic/political/military development so that the Riverlands can bring its full potential to bear on its various challenges. If the Riverlands could raise 40-45,000 men as their population indicates they ought to be able to raise, or if their borders were better guarded by stronger castles, then they’d stand a much better chance against the Westermen, the Ironborn, the Valemen, the Reachermen, and the Stormlanders.
  • a stroke of geostrategic luck. Given the multi-front nature of the great game, it’s much easier for the Riverlands to do well if the Vale is fighting the North and/or the Westermen are fighting the Ironbron and/or the Stormlands/Dorne/Reach are all fighting eachother.
  • good leadership who can combine diplomatic and military talent to achieve one doable objective at a time. For example, if the Riverlands could work out deals with other kingdoms that would allow it to redistribute resources from one or two fronts, that would allow them to concentrate their resources in another direction. LIkewise, while absorbing the Crownlands is a reasonable goal, making a frontal assault on the Bloody Gate or picking simultaneous fights with all of its neighbors at once. 

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