Unfortunately , I am the High King of Skyrim . allegedly <| sep |> but it simply does not match up to the Agricultural capabilities of Whiterun Whiterun hold is mostly tundra which is terrible for farming where as all of the rift , is woodland , which can be converted and used can be used . There is a reason why tundra isn ' t historically used for farming . Also there is a straight road from Eastmarch to the rift and all the lakes of the rift flow into river next to windhelm . So good transport links IMO . A quick google tells me that Aspen wood is tougher than pine making it better for ships , shields and fortifications and therefore better than falkreaths pine forests . Pine is only good or ikea furniture and lollipop sticks , not for war . Whiterun is only important because it is in the centre . not much use when Ulfric burns it to the ground . They ' re in control of the forts , not the land . If a military controls the forts they control the land . Not to meation that most of the forts they control are on major roads . If they are positioned to take Sungard then they effectively cut the reach off from Falkreath hold . They also own ' broken tower redoubt ' that sits upon another major road . IF they control all the settlements on the eastern border then it would be very easy for them to blockade and steal any gold bold from the reach . They are more than just a bunch of savages , they ' ve taken the reach before and they could easily do it again . If they control forts and redoubts and camps and mines then they are more than just a minor pain . TheyWe don ' t see it happen because it ' s a game . Don ' t confuse game mechanics with lore . nothing happens in game unless the LDB is involved and the LDB captures sungard for whatever side he is allied with . If a lore note say the forsworn are in a position to capture sungard then they probably are able to do so . Firebombing Whiterun would be insurmountably stupid . Burning down whiterun is an incredibly smart thing to do . Why would Ulfic want to waste men on a seige when it could be burnt down by his enemies . better just burn it down and use the nearby fort as a base instead . much better defended and not made of wood . Any city with 2 meter high walls and made of wood is not defensible . One pissed off fire mage could level the city in an hour .