Time-Skip

Within a dimly lit room, two men sat at a table opposite each other. Both silently observe and analyse their opponent with firm eyes and a neutral expression.

The first had long brown hair with a thin yet finely maintained beard, strong nordic features, and wore extremely luxurious clothes.

The other had average length dirty blonde hair, a cleanly shaven face with the beginnings of teenage fluff growing, blueish-green eyes, and wore faultless grey robes that barely concealed the muscular body hidden beneath it.

They continue to stare at one another for another five minutes until someone makes the first move to speak. "It's good to finally meet you face to face lad, with all this secrecy, I was beginning to think you were playing me."

Michael gives a light smile and casually folds his legs, "Maybe I was? Maybe I still am?..." he shakes his head, "The only reason I'm meeting you now is because you kept moaning on about it. Has anyone ever told you that you act like a bored housewife, Brynjolf?"

Brynjolf laughs in response, clapping his knee a couple times, "Haha! Hardly! Most are too scared of the Guild to even look at me, let alone say something like that! It's good to know some still have some steel left in them... But I suppose I shouldn't be surprised, you've got quite a lot under your belt now, haven't you lad?" he holds up his fingers and begins listing some off,

"Leader of the most competent adventurer groups with fame comparable to the Companions... One of the most powerful magic users in Skyrim and wielder of unique magic... One of the richest men in Skyrim... Let's not mention your skills as an assassin, and secretive business ventures."

"Are we going to get to business or are you just gonna keep sucking me off, Brynjolf?" Michael replies, feeling slightly embarrassed at having everything he'd been up to listed off so easily.

Brynjolf nods, "Fine. What's got you interested enough to finally meet me? Ah, don't tell me... Was it those fools trying to push you again?"

Michael shakes his head, "No, they learned their lesson the last time... I want to know our progress with my business, SkyRend?"

Brynjolf taps his foot while in thought, "You mean that engineering project with all those ballista? What of it?"

"How many siege engines have been built, are the Stormcloaks or Imperials aware of their existence yet, and have the locations for stores in each Hold been picked yet?"

Brynjolf huffs under his breath, "You say it like it's so simple... Do you know how hard it is to keep literal war machines out of the eyes of either group?" he lets out a weak sigh, "They are secret for now, the thirty or so that've been made, but who knows how long that will stay. What are you even going to use them for? Planning on backing someone? Or maybe taking a piece for yourself?"

The Civil War had only begun a week ago with Ulfric Stormcloak declaring War on the Thalmor, and subsequently the Empire due to the existence of the White-Gold Concordat. No one was surprised by this of course, but it still made Brynjolf wary of Michael's intentions since his SkyRend business had been constructing siege engines for months now.

Michael shakes his head, "I am building them for everyone, but they will not be used against either faction. It might not make sense to you now but, it will when the time comes."

...

"Whatever, as long as it continues making gold, I suppose it doesn't matter." the man shrugs.

The SkyRend company was actually one of the most profitable businesses in the whole of Tamriel right now. While Michael's focus with it was preparing for the Dragon Crises, that didn't mean he intended to lose money either. It was an engineering company, and he'd used modern knowledge to propel it forward.

There wasn't anything too blatant, no advanced machinery, no guns, no advanced knowledge, not even modern metallurgy... Instead, their most popular item was Grandfather clocks. There were many varieties of them, but generally it was the rich and affluent who purchased such things. Since it was a unique technology in this world, Michael could charge whatever he wanted for it.

Sure, there were sundials and some magic to help folks keep track of time, but many were simply too lazy to use such things. Sundials are inaccurate or useless depending on the weather and or time, and the timekeeping magic being difficult to learn since it was an Adept level spell.

His clocks were simply the best option for unmagical rich folk, not to mention being great conversation pieces and things to brag about to their rich buddies. It'd even caused a sort of competition amongst the rich to see who could get the most expensively designed clock...

People would eventually figure out how to make their own of course, but by the time that happened, his SkyRend company would have stores in every hold, perhaps even a presence in Cyrodil and other provinces... After all, time was money, and everyone could use a clock.

The most important thing however, was the fact that his position as leader of the company was completely hidden. He allowed Brynjolf to handle the managing of it, and in return, the man would receive a percentage of the profits along with the ability to have Thieves make occasional use of his stores.

Brynjolf leans forwards in his seat, "So, you won't take any side in the war? I'd have thought someone like you would back the Imperials." he shrugs, referring to his rather well-known relationship with Tiffania.

"My relationship with Tiff is part of the reason I won't back anyone. The Empire are too busy sucking the Thalmor's cocks to care about individuals or what the Elves are doing to Skyrim's citizens under their noses.

My reason for not joining the Stormcloaks is similar but different. Most of its members hate Elves, and even if they win against the Imperials, it'll be the Thalmor they have to fight next... Not the weak forces they've been sending to keep the Imperials on their toes, but a full-scale army. I know they won't win, you know they won't win. To me, both sides are fighting a losing battle."

"Yeah, my thoughts are the same lad, why'd you think I became Jarl? Can't have Riften bumbling into this shit show and getting the Guild involved."