Okay so I just completed the MQ where Riften is exchanged for Falkreath, and I was a bit surprised when Tullius said he was replacing the former Jarl with a self confessed affiliate of the Dark Brotherhood and the Thieves Guild. What I don't understand is how the Penitus Oculatus allows this to slip. How does a woman who for all intents and purposes is the head of underworld activity in Skyrim become the Jarl of an important and strategic hold? Wouldn't this create more problems for Skyrim, and the reputation of the Empire? How does she benefit the Empire? Is the Empire in such dire straits that they have to select a kingpin to govern for them?

One theory I had was that Black Briar had all of the affiliations necessary to make Riften an efficient Hold. She had the power to bring everyone underline, and her position as Jarl makes her official and recognized by the Empire (though it was already assumed and known throughout the Rift that she was in control, and presumably other holds.) It does seem to conflict with the goals of the Penitus Oculatus though, since her official title and whatever benefits come from it can provide many things to their enemies - notably the Dark Brotherhood.

But here is another thing! How much longer will Ulfric Stormcloak deal with this? If Maven Black Briar was the unofficial head of Riften in the first place, a city that was under control of the Stormcloaks, why did they let the Imperial puppet wander around in public? It must be assumed that Black Briar was in cahoots with the Empire long before they decided to put her in control of Riften. An untrustworthy asset in control of so much territory would doom the Empire. Why didn't the Stormcloaks simply pick her up off the street or put a dagger through her heart? For fear of ramifications from the underworld? Possibly, though kingpins dying in the streets is to be expected, and surely there are others in Skyrim's underworld who would gain should Black Briar removed. Perhaps Ulfric Stormcloak should be bargaining with them.

Black-briar already controlling all of Riften even when Law-giver was jarl, this was just making her rule official.

She isn't the first corrupt official the Empire had. plus don't forget that her ties to the TG and the brotherhood are on the hush hush. no one knows anything about that. and the ones who know are either corrupt themselves or paid to keep their mouths shut.

Ulfric doesnt have the time to look out for each hold, each city has its own jarl who operates how he sees fit. Riften is under Lialia law giver's authority and so are the city guards. the Jarl's court is corrupt so Maven and her contacts are safe.

At least she is better than the silver-bloods.