I'm going to wargame a few skyrim civil war scenarios
If the imperials win the civil war:
It may look like a resolution on paper. Ulfric is dead or captured, the Stormcloak leadership is broken, and Imperial authority is restored across all nine holds.
But the Empire has won the battle and inherited the problem.
The underlying grievances that started the war are completely unresolved. The White-Gold Concordat still bans Talos worship. Thalmor Justiciars still operate in Skyrim. The humiliation that drove tens of thousands of Nords to take up arms against the Empire is still sitting there, unaddressed, the day after Ulfric dies.
The Empire wins a damaged province full of people who hate them, inherits all the underlying tensions, and will march into the Second Great War with a sullen Skyrim rather than a willing one.
Within a generation — call it fifteen to thirty years — the conditions for another uprising mature. Nord culture has a long memory and a strong martyrdom tradition. The Stormcloaks who died become legends. Their children grow up on those stories.
The trigger probably isn’t another Ulfric. It’s more likely a Thalmor atrocity that goes too far — a particularly brutal public execution, a massacre of civilians at a Talos shrine, something visceral and visible that crystallizes resentment into active rage.
The second rebellion is potentially more dangerous than the first because it won’t have Ulfric’s particular political baggage. A new leader without his divisiveness — someone who can hold both the Talos faithful and the more pragmatic Jarls together — could build a broader coalition than Ulfric managed. A Whiterun which actively joins rather than staying neutral changes the military calculus significantly. Skyrim becomes a drain on Imperial resources and attention precisely when the Empire needs to be focused on the Dominion.
I would argue an independent Skyrim is the best case scenario, even for the Empire.
With a Stormcloak victory, Ulfric would almost certainly send envoys to Hammerfell. The Redguards successfully fought the Dominion to a stalemate and signed their own separate peace (the Second Treaty of Stros M’Kai). They have every reason to be friendly with a Skyrim that’s also defying the Dominion. A Nord-Redguard pact is highly plausible. Even if not a full military alliance, certainly a trade, intelligence sharing, and a mutual understanding that they’re the two major human powers operating outside Dominion influence.
Within a few years the pressure on Ulfric to reconcile with the Empire would begin to come, and from multiple directions:
Jarls with trade interests would feel it first. Skyrim’s economy runs on Imperial trade routes — metals, furs, lumber moving south through Cyrodiil to reach broader markets. An indefinite cold war with the Empire means tariffs, blockades, and economic stagnation. Thane Erikur of Solitude types — merchant-aligned, pragmatic — would be pushing for normalization within two or three years once the victory euphoria fades and the hold’s treasury starts feeling the pinch.
Military advisors who understand the Dominion’s actual strength would be the most urgent voices. Any competent Nord general who’s seen Thalmor Justiciars operate, who’s read reports from Hammerfell about what the Aldmeri army did there, knows that Skyrim alone cannot hold a sustained conventional war against the full might of the Dominion. The mountains buy time, not victory.
If Skyrim and Hammerfell formalize their defensive pact first, it potentially gives the Empire an indirect route back in.
The Empire could seek better relations with Hammerfell — which it exiled and abandoned — as a confidence-building measure. Hammerfell, now allied with Skyrim, becomes a bridge. A three-way arrangement where Hammerfell is the trusted intermediary between two parties who can’t directly reconcile without losing face is historically very plausible. It lets Ulfric say he’s honoring his Hammerfell commitment that happens to include Imperial forces, rather than saying he’s allied with the Empire directly.
The brutal irony is that the Thalmor, by forcing the White-Gold Concordat and triggering the civil war, may have accidentally created the conditions for their own defeat. A battered but surviving Empire, an independent and battle-hardened Skyrim, and a Hammerfell that already proved the Dominion can be stopped — those three together, even without a formal alliance, represent a threat the Dominion didn’t face in the first war. The Thalmor’s greatest strategic failure may be that they let all three of those human powers survive long enough to eventually point in the same direction.
Note:
There is only one scenario where an Imperial victory produces a positive outcome and it is very unlikely. Where a politically talented Emperor — possibly a successor to Titus Mede II who has more room to maneuver — recognizes that the Concordat is destroying the Empire from within and engineers a situation to get out of it. This might involve deliberately provoking the Dominion into a war on favorable terms before a second Nord rebellion forces a two-front crisis, or building the military capacity through Skyrim’s continued participation to make the Dominion back down diplomatically.
The key variable is whether the Empire can hold Skyrim’s loyalty long enough to rebuild military strength. That requires giving Nords something — not full Talos legalization necessarily, but visible signs that the Empire is working toward it and genuinely values Nord participation. Small gestures matter: Imperial commanders publicly respecting Nord traditions, limits placed on Justiciar operations in exchange for Nord military service, a Nord appointed to a high Imperial position. I feel this is less likely to occur, requiring many different things to go right simultaneously.
The civil war itself, from a purely strategic perspective, is almost irrelevant to the actual civilizational conflict that's coming. The Thalmor engineered it precisely because they understood this. Whether Ulfric wins or loses, the Empire enters the next great war weakened, divided, and fighting with one hand tied behind its back.
The only scenario where the outcome of the civil war genuinely matters is if one result produces a united human coalition — Empire, Skyrim, Hammerfell — that enters the Second Great War with combined strength, shared purpose, and resolved internal politics. That requires either the Stormcloak victory scenario where Skyrim fights as a free ally, or the Imperial victory scenario where a politically gifted Emperor manages to turn Skyrim's resentment into motivated Imperial service rather than sullen occupation.