Skyrim is home to many distinct groups and organizations, each vying for the Last Dragonborn's membership. Every faction holds different strengths, bonds, and ideals that cater to different walks of life. Each organization offers many reasons for joining, most compelling of which often come from its leader. The head of a faction is more influential than any other element.
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The leaders of Skyrim's prominent groups are among the realm's most renowned and powerful individuals. These men and women – and one dragon – are masters of their craft who garner respect from allies and enemies alike. However, many only recognize these great leaders for their exploits rather than their story as a whole.
General Tullius
General Tullius is the stoic leader of the Imperial Legion in Skyrim, who is trying to quell the Stormcloak Rebellion and restore order. The Empire believes Tullius to be the only man capable of such a feat and has put their faith in him alone. While General Tullius appears to be a generic militant commander, there is far more to his character.
Although he despises Ulfric Stormcloak, Tullius sympathizes with the rebels and Nords. In fact, he expresses his discontent for both the Aldmeri Dominion and the White-Gold Concordant. His resentment of the High Elves is ironically on par with Ulfric's — so much so that he once considered aligning with the Stormcloaks.
Ulfric Stormcloak
The divisive leader of the Stormcloak Rebellion, Ulfric, and his rebels fight against the Aldmeri Dominion and, by extension, the Imperial Legion. Many consider Ulfric to be Skyrim's best hope, while others view him as its worst enemy. Regardless of others' views, Ulfric stays true to his cause, fueled by the horrors of his past.
Before the Great War, Ulfric studied the Way of the Voice under the Greybeards. However, he forfeited this opportunity to side with the Empire during the Great War. Upon the Legion's surrender, Ulfric was mortified by all that he and Skyrim sacrificed for nothing. This led him to take dire measures against the Aldmeri Dominion, and consequently spark the SkyrimCivil War.
Kodlak Whitemane
Though the wise Harbinger of The Companions is no longer a fit warrior, Kodlak still aids Skyrim and its people through The Companions. Despite being a proud member, Kodlak holds an opposing disposition towards the group's ideals. He pursues diplomacy, loathes lycanthropy, and discourages revenge, a far cry from The Companion's beliefs and his past.
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Kodlak was a bodyguard working in Hammerfell until former Harbinger Askar took him in. He progressed quickly, eventually becoming Harbinger of The Companions in 4E 181. During this time, Kodlak performed great feats, such as slaying 100 Orc berserkers alongside Skjor. He faced any issue head-on without considering peaceful resolutions, which is a far cry from his character now.
Paarthurnax
Paarthurnax is the enigmatic grandmaster of the Greybeards. Despite being a dragon, Paarthurnax is diametrically opposite to his brethren. He is not hubristic, violent, nor greedy, and discourages those that are. Paarthurnax overcame his draconic nature through Jurgen Windcaller's philosophy, the Way of the Voice.
Before, he was as malevolent as the World Eater himself. During the reign of the Dragon Cult, Paarthurnax was among Alduin's loyal lieutenants. He carried out atrocities in the World Eater's name without remorse. When Alduin's influence over both man and dragon waned, Paarthurnax betrayed him, teaching the Nords how to use the Thu'um. Despite bringing about the dragons' downfall, the Blades deem him a high priority target.
Delphine
Delphine is the skeptical grandmaster of the Blades. With the aid of the Last Dragonborn and the loremaster Esbern, Delphine hopes to return the Blades to their glory. She believes the Blades may once again take up their former role as dragonslayers.
However, Delphine was not always as exuberant and was once more reserved. During the Great War, Delphine orchestrated many crippling operations against the Thalmor. She became a high priority target, and the Thalmor made many attempts on her life. When the Great War came to an end, the Blades had fallen, forcing Delphine into hiding.
Mercer Frey
Mercer Frey is the duplicitous leader of the Thieves Guild. Under the guise of the Guild Master, he has been robbing the guild and compromising their security. Mercer continued his deception until the Last Dragonborn, Brynjolf, and Karliah stopped him once and for all.
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Before becoming the leader of the Thieves Guild, Mercer was a student of the Guild Master Gallus Desidenius. He became a prominent member of the guild and a Nightingale of the Daedric Prince Nocturnal. Using his newfound membership, Mercer stole Nocturnal's prized artifact – the Skeleton Key – and killed Gallus, assuming the role of Guild Master.
Astrid
The stoic leader of the Dark Brotherhood, Astrid holds the interests of the Brotherhood at heart, yet she despises its ancient ways. When her leadership is threatened, this leads Astrid to work with the Penitus Oculatus, resulting in the Brotherhood's near-annihilation and her own death.
Despite this destruction, Astrid only acted to try and preserve the Dark Brotherhood. Astrid joined the Brotherhood after killing her uncle, who made "unwanted advances" on her." Since then, she rose through the ranks, eventually becoming the faction's leader. Without the Night Mother or the Listener, Astrid had to depend on authoritarian leadership alone. She became accustomed to this structure and doesn't wish to return to the brotherhood of old.
Viarmo
As the passionate headmaster of the Bards College, Viarmo stresses the importance that bards hold in the world's affairs. A key philosophy he holds is that bards must strive to retell Skyrim's history, and do their best not to make it. While much about Viarmo is unknown, his fervent love of recitals, song, and poetry speaks volumes.
After Jarl Elisif cancels the annual festival, the Burning of King Olaf, Viarmo does everything in his power to change her mind. To him, canceling the festival tarnishes not only tradition but the Bards College's role as storytellers as well. Viarmo employs the help of the Last Dragonborn to recover King Olaf's Verse, revitalizing the festival and granting it credibility.
Savos Aren
Savos Aren is the esteemed Arch-Mage of the College of Winterhold. Under his guidance, the College can practice all forms of magic with little restriction. Moreover, Aren ensures that the institution remains independent, aside from his Thalmor advisor Ancano. Yet though he has achieved great feats, nothing will overshadow Aren's greatest failure.
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When Aren was an apprentice at the College, he and his colleagues underwent an expedition to Labyrinthian. Here, they hoped to unveil the mysteries of the renowned mage Shalidor. Unfortunately, Labrinthyian was far too dangerous, resulting in all but Aren perishing. Savos sealed Labyrinthian's dangers away and eventually became Arch-Mage; yet, he never forgot the incident.
Isran
The tenacious leader of the Dawnguard is strict and unyielding in his fight against the emerging threat of the Volkihar Clan of vampires. While Isran's goal is noble, his motivations hinder his objective. He does not fight for the greater good but instead seeks vengeance upon vampires. Isran holds a personal vendetta against vampires that goes back many years.
Long ago, a cult of Molag Bal vampires killed Isran's family while he watched. Soon after, he joined the Vigilants of Stendarr to slay vampires and defend the innocent. However, Isran left the Vigilants, deeming them too weak to achieve their goals. With the aid of old friends, he eventually re-established the vampire hunting order known as the Dawnguard.
Lord Harkon
The megalomaniac ruler of the Volkihar vampire clan is immensely cruel, even by a vampire's standards. Harkon lusts for power, willing to do anything to further himself. He is more than willing to sacrifice his wife and daughter if it means achieving his goal.
Even before becoming a vampire, Harkon held this insatiable lust, only to a lesser degree. In life, Harkon was a tyrant, thirsting for wealth and power regardless of his people's suffering. Harkon could not bear losing all that he had attained by reaching the end of his mortal life and made a deal with Molag Bal to live forever as a vampire lord. Even then he was not satisfied, allowing his desires to supersede all else, even family.