It was another beautiful day in the Cloud District. Do you get to the cloud district very often? Oh, what am I saying, of course you don't. Anyway, if you didn't know, the cloud district is the highest level of the city, where the palace of Dragonsreach and the Dragonsreach dungeons are located. Generally only the wealthy and powerful are found there. And the guards of course, the guards are there.

Whiterun-Guard was one of those guards of Whiterun stationed in the Cloud District. His cousin was out fighting dragons and what did he get? Guard duty. But, unbeknownst to most, this Whiterun-Guard also had various connections to the underworld. He was in tight with the Dark Brotherhood, the Thieves Guild, and the Outlaws, brigands, and bandits of the tundra. His hands were dirty to say the least, as he oversaw a booming skooma smuggling operation, along with the fencing of stolen goods and the extortion of various rackets throughout the city. 

"I mostly deal with petty thievery and drunken brawls. Been too long since we've had a good bandit raid." He was known to say to passerby. But the reason there were no bandit raids was because the bandits already controlled the city.

The illicit operations were not only lining his pockets, but raising his status in the city guard. The Jarl had taken a special liking to him, completely unaware of his life in organized crime. It wasn't long before his connections to the law made him an ideally placed candidate to head up a criminal operation of his own from the Cloud District.

Godfather Marston of the Outlaws noticed this, and called him to a meeting out in the woods by a campfire, where they toasted sweetrolls over the flames and discussed the opening of a new criminal enterprise in the city. They'd had a working understanding for some time now, with Whiterun-Guard assisting Marston in several Outlawed endeavors. They would now expand on that understanding, and Whiterun-Guard would be his captain, working directly within the district. This was ideal for the guard so as to not arouse too much suspicion within the ranks of the barracks. He would begin operations immediately, with his hands Toast and Arcturus in tow. 

Whiterun-Guard decided to name his organization Dragonsreach, and began integrating more guards into his schemes. It wouldn't be long until he had more sway in the city than the captain of the guard and that sleazy Jarl Balgruuf. Hell, maybe he'd even get to go inside the great hall and chat up Lydia, the beautiful housecarl swordsmistress he'd long had a crush on.