The Dragonborn uses the civil war in Skyrim to further his own political ends--playing the Stormcloaks and the Imperials against each other. He became leader of the Companions based in Whiterun; the legendary fighters and sellswords descended from Ysgramor and his 500 Companions. The Companions under the now deceased Kodlak Whitemane were once neutral in the conflict. Under him, they sided against the Imperials but by his enthralling leadership, the Companions worshipped him as Ysgramor Incarnate for besting Hircine in the hunting grounds, destroying the Silver Hands, and slaying many dragons that preyed upon the people of Skyrim. Shunning the corrupting influence of the Thalmor-controlled and decrepit Mede Empire and the brutal and insular rule of the Stormcloaks, the Dragonborn declared before his Companions a third choice: an open and independent Skyrim free from foreign occupation, religious persecution, and brutal tyranny under his rule His Companions would have it no other way. He recruited many more fighters into the ranks of the Companions. Though his commanders and sub-commanders were mostly Nords, the rank-and-file were of all races, proving he had some modicum of racial and ethnic tolerance. His Companions would form the bulk of his burgeoning and powerful army in his road to rule.
Before he became leader of the Companions, he had already laid down the groundwork for his rise to power. As the head of the Thieves Guild in Riften, he had restored the fortune and glory to the Thieves yet they became more than that. They were the Dragonborn's eyes and ears throughout Skyrim. He had created a lucrative and elaborate criminal ring that stretched from Markarth to Eastmarch, from the Pale Pass to the Northern Sea. His minions traded everything including coin, jewels, weapons, minerals, slaves, and drugs and they served as his intelligence network. He made himself and his minions and supporters very rich. None more so than Maven Black-Briar, the matriarch of the Black-Briar family, who controlled Riften from behind the scenes. With his help, Maven was able to all but dominate Jarl Laila Law-Giver (who would soon lose her two feuding sons to the Dragonborn's Dark Brotherhood assassins) from behind her throne--ensuring that he had a powerful ally in Maven.
Shortly thereafter, the Dragonborn joined the Dark Brotherhood assassins. Bereft of the Night Mother and the Five Tenets, they were a wayward group whom he quickly assumed control. Posing as the Listener of the Night Mother, he quickly undercut the previous leader, Astrid. More and more of the initiates followed his lead than hers. Her attempt to betray him to the Imperials after killing members of Emperor Mede II's family failed which resulted in the near destruction of the brotherhood at the hands of the Penitus Oculatus. He went on to wreak his vengeance against the Empire. He slaughtered the commander of the Penitus Oculatus and his agents and even killed Emperor Titus Mede II himself aboard his Imperial flagship, the Katariah. The Dark Brotherhood gained enormous prestige from all dark corners of Tamriel and soon the Dragonborn built up the guild again, stronger and better than ever. As the leader of the Dark Brotherhood, he can order the deaths of thousands with a mere whisper to his fanatical thralls. He possesses an unparalleled network of skilled wet-workers and saboteurs to complement his intelligence network among the Thieves Guild and ensuring his own personal security against likewise.
Later, the Dragonborn got involved in the troubles of Markarth located in the region known as the Reach. Markarth and the Reach were under the oppressive thumb of a rich Nord family known as the Silver-Bloods. Their word was law in this part of Skyrim. He learned that a barbaric aboriginal race made up of Breton, Nordic, and Orcish stock known as the Reachmen inhabited this land long before the Nords' ancestors came from Atmora. The Reachmen, also known as the Forsworn after their rebellion following the recent Markarth incident, had fought a long war of rebellion against the Nord occupiers. The source of the Silver-Bloods' great wealth was the mining of silver ore and the means of procurement was the massive slave labor used to dig up the silver from Cihdna Mine. The majority of the slaves were Reachmen but many were not but being pushed to the extremes by the Silver-Bloods and their slave drivers caused them all to embrace the Forsworn Rebellion. They were lead by Madanach, the King of the Reachman, who was also imprisoned in the mines whom the Silver-Bloods used to control the slaves. The Dragonborn formed an alliance with Madanach and engineered the Forsworn's escape from Cihdna Mine. Many Markarth citizens, soldiers, and some of the Silver-Blood family were killed in the uprising. King Madanach owed his life to the Dragonborn and promised eternal fealty and aid him should ever the need arise.
During the fight against Alduin and his draconic horde, the Dragonborn required the use of Dragonsreach Courtyard at Whiterun to conjure and capture Odahviing, an ancient and powerful dragon who defected from Alduin's ranks, to employ against Alduin. To achieve this required the Imperials and the Stormcloaks to agree to a temporary White Peace. He convinced both parties to meet at High Hrothgar with the Greybeards presiding. In accordance with the Dragonborn's designs, Jarl Ulfric Stormcloak would take Markarth and in exchange, General Tullius would take Riften. In addition to eventually stopping Alduin from eating the world with the binding of Odahviing to his will, the exchange of territories between the Stormcloaks and the Imperials fulfilled his political aims. With the Imperial-align Jarl Igmund deposed, Jarl Thongvor Silver-Blood now ruled Markarth with outright brutality; fueling the growing Forsworn rebellion that was now far more organized and stronger with King Madanach free from chains and growing strong in his mountain of power at Druach Redoubt. The Stormcloak sympathizer, Laila Law-Giver, was recalled to the Court at Solitude. In her place, was Jarl Maven Black-Briar, who had always ruled Riften in all but name until now but soon her throne room would become her prison because she owed everything to the Dragonborn and she could not dispense with him because he had complete control of the criminal underworld and the Dark Brotherhood--once she was the power behind the throne now she was rendered the puppet and he was the puppet-master. The Dragonborn's two allies, King Madanach and Jarl Maven Black-Briar, would play their part soon enough.
With the destruction of Alduin and his dragonish horde, the Dragonborn gained such enormous prestige, glory, and honor as the savior of Skyrim. Soon after those events were laid to rest, The White Peace of High Hrothgar was forgotten and the nascent civil war proceeded apace. He sent out secret agents to feign loyalty to both the Imperial Legions and the Stormcloak rebels. Thus his spiders crept into the ranks of both factions and through them he learned of the resting place of the fabled jagged crown in Korvanjund Barrow, said to be the crown for all true Kings of Skyrim. Several parties of Imperials and rebels sought it out for their respective lords but his own Companion army ambushed and killed them all and claimed it for the Dragonborn. He would bear the jagged crown upon his furrowed brow in due time.
His agents intercept couriers from the Stormcloaks and the Imperials bearing messages "requesting" that the Jarl Balgruuf of Whiterun chose which side he was on. Through disinformation and subterfuge, he manipulates both the legions and the rebels to come to blows at the Battle of Whiterun. And so it goes, with the Imperials defending the city while the Stormcloaks laid siege. The Dragonborn and his Companions donned Stormcloak armor and seized the Jarl and his court--secured them in the dungeon while the other Companions fall upon the last Imperial defenders--subduing and imprisoning Legate Rikke and Legate Quentine Cipius in the process. Galmar Stone-Fist, Jarl Stormcloak's second-in-command, is astonished to find his seeming brothers-in-arms had managed to infiltrate the city. The Dragonborn's "Stormcloaks" allow Galmar and his tired army within the gates. He reveals himself as none other than the Dragonborn. He strikes down Galmar, cutting of his right hand, and his Companions cuts down the remaining Stormcloak army. Galmar is imprisoned in the palace dungeon. The Dragonborn is proclaimed the new Jarl of Whiterun. He quickly consolidates his power over the city. He names the Grey-Manes his allies. He makes Vignar Grey-Mane his steward and convinces Olfina Gray-Mane to be one of his shield-maidens (his bodyguards in theory, glorified concubines in reality). He casts down the haughty Battle-Born clan from his court. Talos worship is no longer forbidden within the territory of Whiterun.
With General Tullius and Jarl Stormcloak reeling from the mutual disaster at Whiterun and faced with the loss of serious manpower and their respective field commanders, they have no choice but to shore up their remaining strength, while the Dragonborn moves in on Falkreath. He deposes the weakling Jarl Siddgeir and restores Dengeir of Stuhn back to his rightful Jarldom. Just as the Gray-Manes had done, Jarl Dengeir foregoes his alliance with Jarl Stormcloak and instead swears eternal fealty to the Dragonborn. Overwhelmed by his charisma presence and the sight of the Jagged Crown on his head, Jarl Dengeir would remain forever loyal.
Events happen very quickly. The Dragonborn sends a regiment to Markarth and another to Riften. At his command, King Madanach began the Forsworn rebellion. The combined forces of the Companion army and Madanach's Reachmen overwhelm Markarth's defenses. Largely, the slaughter of innocents is kept to a minimum. Jarl Silver-blood and the rest of the family are captured. One of the Dragonborn's envoys sent from Whiterun presides over their agonizing executions; molten silver poured down their throats in retaliation for the many years of oppression and profit-driven slavery. Meanwhile in the Rift hold, Jarl Black-Briar opens Riften's gates to the other Companion regiment. The takeover is peaceful. Jarl Black-Briar cooperates fully with the Dragonborn's demands lest she receive a knife in her back from one of his many murderous Dark Brotherhood thralls that prowl around her court. The Imperial and Stormcloak controlled fortresses that are conquered; the Hero of Skyrim liberates the respective war prisoners of each fort. He persuades them to serve him instead of their former masters who abandoned them to their wretched fates. His spies and scouts cut off the supply lines of both the Imperials and the Stormcloaks and through false fronts and misinformation, diverts their forces into doomed ambushes or areas where they were not needed-overextending and exhausting the logistics and supply trains of both armies.
With the holds of Whiterun, the Reach, and the Rift and its cities, settlements, and key fortresses under his control, the Dragonborn emerges as a serious contender for sovereignty of Skyrim. Though General Tullius and Jarl Stormcloak were still bewildered by their drastic losses; each believing the other side responsible for their losses, an astonished General Tullius receives the Dragonborn's diplomatic emissaries sent to Castle Dour. They feed him lies and honeyed words about how the Dragonborn saved Whiterun from Stormcloak annihilation, how he emerged as the defacto ruler of Whiterun, and how he is taking the fight to the traitorous Ulfric in Eastmarch. They buy the Dragonborn time while he leads the best of his Companions against Jarl Stormcloak of Windhelm. His armies conquer the Stormcloak fortress in the region of Eastmarch and soon, his forces surround Windhelm and lay siege to the outer walls of Windhelm. The fighting is fierce on both sides but the Companions' greater numbers and discipline give way. The Companions suppressed the defenders of the castle while the Great Dragonborn employed his thu'um to blast open the gates of Windhelm. The Companions pour in and a tense standoff ensues between the Companions and the Stormcloaks guarding the Palace of the Kings. Rather than put to slaughter potential allies in the war against the true enemy, the Dragonborn challenges Ulfric to a duel to the death to determine for good and all, who will rule Skyrim after the Imperials have been driven out. Ulfric accepts and the two mighty heroes fight each other hand-to-hand. Though Ulfric could best a mere stripling of a boy king in a duel, he was no match for a true warrior and Thu'um master. The Dragonborn gutted the Bear of Markarth and beheaded him; taking from his corpse the symbols of his office. He annexes Eastmarch and places Brunwulf Free-Winter as Jarl-in-charge of Windhelm.
The Dragonborn revitalizes his armies with recruits from the former Stormcloak rebels and of Eastmarch and begins the westward march towards Solitude. Winterhold and Hjaalmarch offer no such resistance given their pitiable state and the Jarls of Winterhold and Dawnstar thus swear fealty to him. He destroys Fort Hraggstad in the region of Haafingar and moves onto Solitude. The capital of Skyrim proves a tougher nut to crack with the bulk of the legions defending it but eventually the tides turn in favor of the Dragonborn. Eventually the outer walls are breached, and the Imperials fall back to Castle Dour, unable to withstand the tide. He and his Companions wade knee deep in the blood of the Imperials. He gave General Tullius a sporting chance at a one-on-one duel but fared worse than Ulfric. Tullius was quickly ran through and his head put on a pike and paraded throughout the streets. His soldiers secured the Blue Palace. He deprived the former High Queen Elisif the Fair of her Jarldom but took her as his Queen to which she dared not object. And all of Skyrim fell under the sway of the Dragonborn.
