The Main Quest: Finale

Special thanks to Kurt Kuhlmann for pointing out some factual errors in an earlier version of this post!

After Paarthurnax, the Main Quest provides very few opportunities for moral agency.  Capturing Odahviing, travelling to Skuldafn, visiting Sovngarde, and defeating Alduin are all dramatic and engaging quests, but they present no significant moral quandaries.  There are, however, some events that bear further examination.

The latter part of the Main Quest reveals that not all of the dragons share Alduin's views. During The Fallen, I learned the shout that summons Odahviing, thus providing me another opportunity to converse with a dragon.  Odahviing is an active ally of Alduin, but when we captured him, he agreed to help me track down the World-Eater in exchange for his own freedom.  Because of his dialogue, Odahviing comes off as an opportunist who betrays Alduin not on principle, but on the likelihood that the Dovahkiin will defeat him:

 
Once Alduin is defeated, Odahviing pledges to aid the Dragonborn whenever he calls; he is not, however, another Paarthurnax, who promises to teach the pacifist Way of the Voice to all of the dragons he can convince.

He might actually succeed, as Paarthurnax and Odahviing are not the only non-hostile dragons in the game.  Until Skuldafn, I had never encountered a non-NPC dragon that did not attack the moment it detected me (or anyone else for that matter).  At Skuldafn, however, I ran into a dragon who, despite being perched directly above the portal to Sovngarde and witnessing my defeat of his comrades, did not attack.  He watched me closely, but made no aggressive moves at all.  Given my experience with Paarthurnax and Odahviing, I decided to hold back, and it began to dawn on me that all of the dragons (not just the named ones) might be morally complex creatures who are as apt to choose "the high road" as their mortal counterparts.  Perhaps this moral range explains why, at the Throat of the World, dragons can be seen celebrating the World-Eater's fall. 

As it turns out, the complicated moral tableau presented at the portal to Sovngarde was reflected on the other side as well.  While the scenes inside the Hall of Valor are interesting from a cultural perspective (of course Nords brawl in Heaven!), the encounters before I met Tsun were the most enlightening:

• Kodlak: It was satisfying to see Kodlak in his beloved Sovngarde.  Even though he had assured me that the purification was successful, I was happy to see the results for myself.

• Torygg: The High King's dialogue suggests that the popular story that Ulfric "shouted him to pieces" is closer to the truth than Ulfric's account, but I'm not sure if this is an important distinction.

• Ulfric: This was by far the most substantial encounter in Sovngarde.  First, it appears that Ulfric's ascent to the Nord Paradise has erased any animosity he might harbor for the man who killed him in battle.  Second, Ulfric expresses a profound and sincere regret for his part in Skyrim's strife.  He stops short of saying that he was wrong, but his sadness is undeniable.  I suspect that, if he had the opportunity to  do it all again, he would probably try harder to convince Torygg of the need for secession, rather than kill him.  This conversation confirmed both my decision to support the Empire and my respect for Jarl Ulfric.

As for the final battle with Alduin, there is little of moral significance to examine, with the possible exception of the emphasis on unified effort.  In order to defeat the World-Eater, I had to join forces with the heroes of old -- perhaps an object lesson on the necessity of community.  Now that I think about it, that may be the best moral for a war-torn Skyrim after all.

Paarthurnax: Further Considerations

The conflict at the core of the Dovahkiin's rise to power is analogous to that faced by Raskolnikov in Dostoyevsky's Crime and Punishment.   Raskolnikov considers himself to be an extraordinary man -- the creator of a "New Word" -- and therefore above the laws of ordinary men.  He finds himself torn between two models of this "extraordinary man": the Nietschzean Übermensch, who subjugates those beneath him by virtue of his greater power, and the Hegelian superman, who transcends the law in order to perform great and noble deeds.  Raskolnikov considers his murder of the evil pawnbroker as evidence of his superior nature; he breaks the law in order to rid the world of a great evil.  Once he does so, however, he finds himself becoming more Nietschzean, seeking power over others for its own sake.

While Raskolnikov only thinks of himself as extraordinary, the Dovahkiin is emperically superior to those around him, capable of supernatural feats beyond those of the most powerful NPCs and creatures in the game.  During the course of the game, the Dovahkiin can defeat Alduin the World-Eater, challenge the Daedra, decide the outcome of the Civil War, and simultaneously become the leader of the Companions, the Thieves' Guild, the Dark Brotherhood, and the College of Winterhold.  Furthermore, the Dovahkiin literally possesses a "new word" -- or, more accurately, several ancient words -- that denotes a unique role in Tamriel's history. The question is not whether the Dovahkiin is extraordinary; the question is whether he or she will take the Nietschzean or the Hegelian route.  Obviously, the player as moral agent ultimately decides which kind of superman the Dovahkiin will become, but the game provides several prominent models of the Nietschzean Übermensch against which the player can be defined.

The central Nietschzean character in the game is, as I mentioned in the previous post, Alduin.  The World-Eater seeks power over mortals and dragons alike, not for the benefit of his kind or the glory of some divine being, but for his own sake.  He conquers because it is his nature to do so.  He does not bother to justify his actions to anyone, because to do so would suggest that someone else has authority over him.  He enslaves or destroys the weak and commands the strong.  He is the lust for power personified.

Paarthurnax provides a useful Hegelian counterpoint to Alduin.  Here we have a being who, like his erstwhile ally, instinctively seeks to conquer, yet consciously chooses otherwise.  In helping the Tongues and the Greybeards, he betrays his own kind and violates his own innate nature to serve a noble cause: the Way of the Voice.  He creates a new law to supplant the Nietschzean rule of Alduin.

Paarthurnax, however, is not alone.  Brynjolf, Kodlak, Argenir, and even Ulfric Stormcloak demonstrate the power of "honorable transgression."  Each of these characters violates some law or taboo or tradition in order to serve, at least in their estimation, a greater good.  While one could argue against the particular motivation in each case (Jarl Ulfric's cause being the most obvious example), these characters are all motivated by something greater than and outside of their own individual selves.

What is noteworthy here is that each of the more Hegelian characters is presented as decidedly more heroic (or at least respectable) than their Nietschzean counterparts.  Paarthurnax's dialogue is eloquent and thought-provoking, while Alduin's is full of self-aggrandizement and menace.  Consider the conflict between Mercer and Brynjolf; the former amasses power and wealth for himself alone, while Brynjolf and Karliah seek to revitalize the Guild and to serve Nocturnal.  Dawnguard presents another example in the persons of Isran and Lord Harkon.  Despite the freedom of choice available to the PC, the game presents the Nietschzean Will to Power as something the Dovahkiin must overcome at every turn.

Perhaps the most prominent example of this bias occurs in the Dragonborn DLC.  During the Main Quest, the Greybeards warn the Dovahkiin not to abuse his power, but in Dragonborn, we are presented with an antagonist who did precisely that.  What separates Miraak from the other two "final bosses" is that he is a dark reflection of the PC: a Dovahkiin who uses his power for himself rather than for some higher purpose.  In other words, Miraak plays Svidrigaïlov to the PC's Raskolnikov.

While one may choose to play a Nietschzean Dovahkiin, the game clearly favors the Hegelian model.  The vast majority of the minor and side quests ask the player to do something for someone else's benefit.  The Nietschzean role-player has to work around that through cynicism: I am doing this favor for the sole purpose of getting a reward.  Of course, a player can wreak mayhem in the streets, but really, almost every scripted quest invites the player to help someone else.  Even the Dark Brotherhood quests are presented in the context of helping the "family."  Furthermore, each main quest (Skyrim, Dawnguard, Dragonborn) pits the PC against a Nietschzean adversary in order to save the world.  At no point can the player choose to join a Nietschzean NPC in his quest to destroy or enslave Tamriel.  Yes, one can join the Volkihar, but Lord Harkon is still the enemy because his insane plan puts all vampires at risk.  One could argue that joining a Nietschzean faction would be nearly impossible to script because a faction centered around an Übermensch would be a cult, an cults negate the agency of the member, which would run counter to the necessary agency of the PC in an RPG.  This objection merely pushes the question down the road: are all RPGs anti-Nietschzean?

In short, Paarthurnax underscores the Hegelian tilt of Skyrim.  How else to understand a game in which one of most beloved characters is essentially a Hegelian version of the Nietschzean villian?

Paarthurnax

As I pointed out in my Diplomatic Immunity post, the main quest of Skyrim does not offer a high number of moral dilemmas.  Even if I were to accept the Greybeards' theory that Alduin's attacks presage the just and inevitable end of this world in preparation for the new world to come, my role as Dovahkiin draws me just as inexorably to a confrontation with the World Eater.  Therefore, despite the high drama and plot tension extant in the main quest, there are only a handful of opportunities for true moral agency.  The quest entitled Paarthurnax presents the fourth and final scripted moral dilemma.

After discovering Sky Haven Temple, Delphine tasked me with helping her to rebuild the Blades.  I was to recruit three warriors whom I thought would be well-suited to the task of hunting dragons and, perhaps eventually, protecting a Dragonborn Emperor.  I chose three followers whom I knew from experience could handle the job: Uthgerd the Unbroken and Lydia (my housecarl at Breezehome) had demonstrated impressive skills in Heavy Armor, One- and Two-Handed Combat, Blocking, and Archery, so they were natural choices; I also selected Brelyna Maryon from the College of Winterhold, whose formidable Conjuration and Destruction talents allowed me to round out a small army of dragon hunters that could bring both melee and ranged attacks into any situation.  Having bolstered the ranks of the Blades to Delphine's satisfaction, we went out on a few successful dragon raids without incident.  I then returned to the main quest, which took me back to High Hrothgar to finally meet Paarthurnax, the leader of the Greybeards... 

[SPECIAL NOTE TO THE READER: While I have clearly indicated in the banner of this blog that spoilers abound, this particular post contains what is arguably the biggest spoiler in the game.  Of course, the game has been out for almost two years now, so anyone reading this blog is probably already aware of the plot twist, but one never knows.]

...who is a dragon!  The animosity between the Blades and the Greybeards now makes sense.  The Blades see dragons merely as a threat to be vanquished, while the Greybeards see them as powerful, near-divine beings, capable of both profound good and cataclysmic evil.

My conversation with Paarthurnax was without a doubt one of the most enlightening in the entire game.  I learned not only about the history of the Dragon War, but also about the conflict at the core of dragonkind: the will to power.  According to Paarthurnax, it is in the nature of dragons to seek power, regardless of mortal notions of morality. He explains his own centuries of peaceful meditation as a constant struggle against his deepest instincts.  For a full appreciation of Paarthurnax's story, I recommend the reader invest some time (about 20 minutes) watching the clip below from another player's YouTube video:

In my next post, I will delve more deeply into the Nietzschean/Hegelian conflict at the core of the Alduin/Dovahkiin battle, but for now, I am limiting myself to the events that occur immediately after this encounter with the "good" dragon.

Aside from teaching me how to use my Shout more effectively, Paarthurnax pointed me in the direction of the Elder Scroll that would enable me to go back in time and learn the Dragonrend Shout that defeated Alduin ages ago.  After finding the Scroll, I returned to Paarthurnax, unfurled the Scroll, saw how a trio of my ancestors banished Alduin from their era, and learned the Shout; this action broadcast my location to Alduin, who showed up to kill me before I could have a chance to defeat him.  Paarthurnax, despite his nature and his previous allegiance to Alduin, battled the World-Eater in the air while I attempted to use Dragonrend to ground him.  Although we did not kill Alduin this time, we managed to drive him into hiding.  Paarthurnax recommended that I find and interrogate one of Alduin's minions in order to learn where he fled -- no easy task.  My next move was to report to Esbern to ask for some advice.

Esbern was more than happy to offer his insights on capturing a dragon, but then he presented me with a new problem; citing his oath as a Blade, he demanded that I kill Paarthurnax, and refused to provide any more assistance to me until I did so.  Delphine seconded his ultimatum, and cut me off from the further services of the Blades.  Once again, I would have to choose sides in a conflict when I'd really rather not.

Actually, Esbern and Delphine express slightly different reasons for demanding the dragon's death.  Esbern points out that, during the first dragon crisis, Paarthurnax was one of Alduin’s lieutenants during the first dragon crisis, and was personally responsible for a whole host of atrocities against man.  The fact he eventually turned on Alduin and helped to defeat him both now and in the past is utterly irrelevant to Esbern; the old dragon must pay for his crimes.  Delphine agreed, but added that Paarthurnax’s betrayal of Alduin indicates a dangerous disloyalty which could turn against me at some point; after all, if he was willing to turn on one of his own, how much more likely that he would turn on a mortal ally?

Of the two objections, Delphine’s was the easier to counter.  By my figuring, there are only two scenarios in which her fears could come true.  Perhaps, at some point in the future, Paarthurnax’s loyalty shifts again, and he decides he was wrong to help me in the first place – or maybe he never really turned on Alduin and was just waiting for his master to return in order to draw the Dovahkiin out.  Should that happen, I am confident that I could dispatch him without too much risk.  The second and more troubling scenario is that Paarthurnax is actually looking to supplant Alduin, and is using me to do it.  What if Paarthurnax helped the original Tongues as a means of getting his superior out of the way?  When they succeeded in sending him into the future (but not destroying him), Paarthurnax decided to wait patiently for Alduin’s return, then teach the Dovahkiin how to destroy him, only to turn on the Dragonborn once Alduin was out of the way.  The problem with this second scenario is that, in order to believe that he could defeat the man who killed Alduin the World-Eater (a dragon he himself dared not attack directly), Paarthurnax would have to be both desperate and foolish, and I doubt he is either.

Esbern’s argument, on the other hand, gave me real pause.  The central question is whether Paarthurnax’s current assistance mitigates his past crimes.  In each encounter with an NPC who has done wrong, I have relied on the presence or absence of remorse as my barometer. To be more specific, I look for remorse in the form of action rather than words.  Sinding said he regretted killing the little girl, but he was unwilling to face justice, so I killed him.  Erandur rejected the Daedric Prince Vermina whom he once served, became a priest of Mara, and risked life and limb to save Dawnstar from its nightmares, so I chose to help him and refused to kill him when Vermina commanded me to do so.  Paarthurnax, as far as I can tell, is more like the latter than the former.  He betrayed Alduin at great personal risk, then devoted the rest of his long existence to helping the Nords master the Way of the Voice.  Furthermore, everyone affected by his previous actions is long dead, so there seems to be little point in retribution.  I fully appreciate the magnitude of his crimes, but to kill him at this point seems unjust. 

Another point to consider: even though they began as an elite squad of dragon-hunters, the Blades served the Emperor as a personal guard, before the Thalmor eliminated them.  I cannot help but be a little put off by the fact that they now refuse to help me unless I follow their commands.  I don’t normally pull rank, but to be fair, I am Dovahkiin.  If anything, the Blades should trust me and follow my commands, not the other way around.  One might argue that the Greybeards would have the similar reaction if I did kill Paarthurnax, but then they never swore an oath to protect me, did they?

Even taking Paarthurnax's crimes into account, I cannot bring myself to kill him.  I may come to regret this decision for a number of reasons, but I believe it would be base ingratitude to kill the dragon who risked his own life to save ours.

A Cornered Rat

About halfway through the Thieves Guild questline, I returned to the main quest, now armed with the knowledge of Esbern's whereabouts.  I began my search of the Ratway by dispatching the Thalmor agents who were also looking for the elderly Blade loremaster.  I carefully advanced through the vaults and into the warrens, taking out a few thugs here and there.  I ran into nothing of moral significance until I reached the heart of the warrens, and as I review the events that unfolded there, I'm sure that the dilemma I faced was in no way scripted by the game.

I found that the warrens were occupied by three madmen other than Esbern: Salvianus, the Imperial Legionnaire whom the Great War drove insane; Knjakr, the Sweeney Todd-like chef; and Hefid the Deaf, a poor beggar woman who mutters a kind of OCD litany.  Salvianus, while clearly insane, was a gentle soul who only wanted to try to explain the hopelessness he felt, so I listened to him as long as I could before moving on.  Knjakr attacked me the moment I tried to speak with him, so I had to kill him in self-defense.  Hefid, however, presented me with an unexpected challenge.

When I interrupted Hefid's incessant listing of common objects, she completely freaked out, drew a dagger, and ran away from me.  I would have been happy to let her go, but for one problem: she ran straight to Esbern's door and continued to brandish her weapon no matter what I did.  When I tried to talk, she didn't respond, preferring instead to throw herself at the heavily bolted door to Esbern's room.

I now had a real dilemma on my hands.  Opening Esbern's door (assuming I could do so), would send an armed madwoman into the deadbolted cell of a paranoid ex-Blade.  At best, he kills her, and probably attacks me as an accomplice.  At worst, she kills him, and the last remaining hope to defeat Alduin is gone.  Because I could not think of a scenario which didn't end with her death, I decided to kill her as quickly and mercifully as possible.

After gaining Esbern's trust and hearing his tale, we set out to find Delphine.  We didn't take two steps outside his door before we were set upon by more Thalmor agents.  We killed them, but poor Salvianus got caught in the crossfire -- his worst nightmare finally coming true.  I paid my respects, then escorted Esbern back to Riverwood.

I don't feel good about killing Hefid, but once I had spoken to her, I don't see how I could have avoided it.  A quick FUS might have pushed her aside, but would probably also have provoked her to attack me.  Furthermore, even if she had survived the initial encounter, what would have happened during the fight with the Thalmor?  And, if I'm being completely honest here, what kind of life did she have, tormented by her obsessive list in her dank, dark cell?  Might she be better off dead?

"Knife. Yes. Book. Yes. Bucket. Yes. Inkpot? No."  R.I.P. Hefid the Deaf

Thieves' Guild (Under New Management)

After taking on the mantle of the Nightingale and defeating the traitorous Mercer Frey, I was tasked with returning the Guild to its former glory by re-establishing its reputation all across Skyrim.  In order to redeem the Guild and earn the title of Guildmaster, I would have to pull off a series of at least 20 small jobs, followed by four larger capers in The Reach, Whiterun, Haafingar, and Eastmarch.  Each job presented its own moral dilemma, which I navigated with varying degrees of success.

Small Jobs

The Bedlam Jobs: These jobs required me to steal at least 500 gold in loot from a given city.  I managed the Bedlam jobs by choosing morally acceptable targets (those who are rich and/or loathsome, such as Erikur) or by replacing the stolen items with items of equal or greater value. The first method played into my habit of passing judgment on NPCs in order to rationalize my actions; the wealthy wouldn't miss the loot, and the reprehensible deserve the inconvenience.  The second method allowed me to create a "no harm, no foul" arrangement with myself in order to assuage any guilt I might feel.  I used both methods for other types of jobs as well.

The Fishing/Heist Jobs: In both cases, the contract was to steal a specific item from a specific person or business.  I tended to favor the "acceptable target" method for the pickpocketing jobs and the "replacement" method for the safecracking jobs.  My logic here was that the items on an NPC were probably of personal as well as monetary value, so replacement would not be acceptable, and I would need to reject any targets from whom I could not justify stealing (see above).  Businesses, on the other hand, are interested in monetary value only, so replacing the stolen items made sense.

The Numbers Jobs: Because there are very few morally acceptable target businesses, these jobs presented a unique problem: on the one hand, forging a business's ledger cannot be "balanced" with a replacement, but on the other, it was heavily implied that the forgeries would only be used to hide Guild activities (as opposed to stealing from the business itself).  Furthermore, I noticed no ill effect of the forgeries on the targeted businesses.  With no good method of balancing the crimes or measuring their long-term impacts, I completed only a few of these jobs.

The Shill Jobs: Similar to A Chance Arrangement, the Shill job required me to plant a stolen item in a random person's house.  Since there is no way to balance this kind of crime, I only did a handful of these, and only if the target was morally acceptable (such as Bolli).

The Sweep/Burglary Jobs: These jobs presented the biggest hurdle for me because they came with a ludonarrative twist.  Both job types required me to steal specific items from a house, so I used the same "acceptable target" and "replacement" methods as in the Bedlam jobs, but I noticed that the items I stole spawned in the house only after I accepted the job.  In other words, if I entered, say, the Atheron residence before taking a Sweep job, none of the target items would be there.  The items only exist when I agree to steal them.  The game does attempt to deflect the ludonarrative dissonance (usually Vex saying something about the target house having recent bought or inherited the item(s) in question), but after the fifth or sixth job of this type, it becomes rather difficult to make a moral investment.  If the items don't exist until I agree to steal them, then there is no real moral question.

Larger Capers (a.k.a. City Influence Quests)

Imitation Amnesty (Whiterun): This quest required me to forge a prison registry in order to provide a new identity for "Arn," a war-buddy of Olfrid Battle-Born.  The moral dilemma is that Arn is apparently wanted for a capital offense in Solitude, but was brought in on a public drunkenness charge in Whiteun.  The new identity will allow Arn to serve his time in Whiterun on the minor charge, then go free.  While my previous forgeries simply allowed the Guild to operate discretely, this one would potentially set a serious criminal free.  There were several complicating factors to consider:

• Olfrid never reveals what the charges are, nor whether Arn actually committed the crime.  Given the events of Unbound, I am well aware that the Empire sometimes plays fast and loose with the concept of "capital offense"; apparently, trespassing and horse stealing fall under that category alongside high treason.  Without knowing what he supposedly did or if he even did it, I had very little way of determining whether sneaking into Dragonsreach to alter an official document was justified in this case.
• As the load screens are fond of pointing out, each hold tracks its crime differently.  Therefore, a crime committed in Haafingar might not warrant extradition from Whiterun.  The fact that Solitude specifically asked Whiterun to be on the lookout for Arn suggests that this is an unusual case -- perhaps involving the war...
• ...on the other hand, Olfrid is a staunch supporter of the Empire, so it's unlikely that he would want to cover up anything treasonous.
• Unlike the small jobs, this job cannot be turned down and replaced with a similar, more palatable one.  Failing this quest would prevent me from becoming Guildmaster.

I agreed to take the job.  Without additional information, I was not convinced that the crime was justified, but as I pointed out in that last bullet, there was a larger picture to consider.  Unfortunately, during the job, I discovered a letter which revealed that Arn was wanted for murder.  Now I had a real problem: do I allow a man charged with murder go free?  The revised considerations:

• I still could not be certain that Arn was guilty of murder.  I knew this argument was losing ground by the minute, but I also knew from previous experience that killing an enemy whom the Hold Guard doesn't recognize as an enemy can result in a murder charge. 
• Taking leadership of the Guild was still my prime motivation for taking the job.  The letter does not change that.

I went forward, despite my misgivings. I really compromised my moral stance this time, and it did not feel good.

The Dainty Sload (Haafingar): This job was morally challenging in and of itself.  I was asked to plant illegal drugs on a dishonest ship captain -- definitely gray and grey morality, but palatable in the context of the big picture: only bad people were being hurt.  The real obstacle was minimizing the collateral damage to the captain's crew; labeled as "Corsairs," the only so-named NPCs in the game, I could not just exterminate them as bandits, even though that is most likely what they are.  I therefore decided to Sneak through the whole thing in order to avoid any unnecessary deaths.  I did, however, opt to pick Sabine Nytte's pocket for the Balmora Blue; stealing from one criminal to frame another seemed justified to me.

Silver Lining (The Reach): Because this quest involved simply retrieving a stolen item from bandits, it was the easiest one to complete from a moral perspective.

Summerset Shadows (Eastmarch): Although not morally complex (wiping out a rival, murderous clan of Altmer thieves), this quest does tap into some other aspects of my playstyle.  As I have pointed out before, I take pleasure in killing Thalmor agents, but not all Altmer are Thalmor.  The Summerset Shadows, while not an official part of the Aldmeri Dominion, strike me as the criminal echo of the Thalmor; unlike other bandit clans, they are comprised of only one race.  Their apparent racism transforms their simple criminal  brutality into an aid to the Thalmor cause.  I would have gladly taken this job, even if I weren't a member of Guild.

The Ceremony: After completing all of the quests in this line, I was named Guildmaster, thereby cementing my control of all of the joinable factions in Skyrim.  I am still not sure if all of the steps along the way were morally worthwhile, but I will stand by my choices.

The Guild restored.

Thieves' Guild (Scoundrel's Folly through Darkness Returns)

Scoundrel's Folly

As I pointed out in my Anniversary Update post, this quest presents some significant challenges to the moral agent.  I was able to avoid the initial problem of stealing from Jarl Elisif in order to gain Gulum-Ei's information by simply Intimidating the Argonian.  Following him into the warehouse, however, was much trickier, but I managed to complete it without killing anyone other than the bandits inside Gulum-Ei's hideout.  I spared Gulum-Ei because, despite the gauntlet I had to run to catch up to him, he did not attack me directly, nor did he even know I was tailing him. 

Speaking with Silence

Speaking with Silence is far more interesting plot-wise, but presents very few moral challenges.  Nevertheless, the revelations in this quest shed some light on the morality of the Guild as a whole.  Without detailing all of the intricate plot elements, I will simply say that The Thieves' Guild as it first presented in Skyrim is a hollow shell of its former self, mainly because of Mercer's betrayal.  Therefore, many of the less charitable first impressions may have been based on an incomplete picture of the Guild.

Hard Answers

The next quest, like Scoundrel's Folly before it, presents a single moral challenge: trespassing into a friendly facility without being caught by the legitimate guards of said facility.  I did not even have to steal anything this time; I made a charcoal rubbing of the artifact I needed and sneaked back out.

Nope.  Not even with a hundred Fortify Carry Weight potions.

The Pursuit

This quest presents a minor dilemma in the person of Vald, the hired thug at Mercer's house.  My options for getting past Vald consisted of the following:

• Kill him
• Persuade him
• Pay his debt to Maven

Vald is initially non-hostile, so killing would have been wrong (he's obviously not very bright, so he probably has no idea that Mercer had betrayed the Guild).  I failed to Persuade him, so paying his debt was the only viable choice.  It turned out to be a minor chore (finding a special quill that Vald lost in transport), and Vald was grateful enough that he vacated his post.  The rest of this quest pitted me against bandits in Mercer's employ, so there were no further moral dilemmas.

Trinity Restored

This quest reveals the deeper essence of the Guild, which confirms my earlier suspicions about it being much more than a gang of criminals. Even though I was required to enter into a contract with the Daedric Prince Nocturnal, devotion to this entity consists of doing what I was doing anyway: thieving.  Other than that, there are no further opportunities for moral agency.

Blindsighted

Aside from killing some bandits and a bunch of Falmer, we had to confront and kill Mercer Frey.  Very straightforward.

Darkness Returns

None of these tests of strength, wit, and stealth are morally complex.

These quests form the main part of the Thieves' Guild line, and are engaging from both a moral and an narrative perspective.  By completing them, I learned that the Guild exists to honor stealth and regulate crime, not merely to line the pockets of its members.  When it is running at full strength, it is an organization that stabilizes the community by setting standards of criminal behavior and driving out destabilizing elements.  As a moral agent, I was able to find justification for their existence, but that justification was about to be tested in the final part of the questline: Under New Management.

Update: Boethiah's Calling/Unearthed

I am interrupting my treatment of the Thieves’ Guild questline in order to provide an update on one of the Daedric quests that has been a real thorn in my side: Boethiah’s Calling.  In my first post on this quest, I declared that I would not complete the quest unless I found a follower who deserved to be sacrificed – a condition I did not expect the game to meet.  While some of the available followers inhabit a moral grey zone (e.g. Janessa), no one outside of the Dark Brotherhood really deserved to be deceived and murdered, and I could not justify joining the Brotherhood (and committing the prerequisite murders) just to sacrifice one of them.  Therefore, I resigned myself to leaving the quest incomplete (since there is no failure condition) for the remainder of the game.

The Dragonborn DLC, however, provided exactly the kind of follower I was looking for.  Most of the Dunmer NPCs  I met in Skyrim were either enemies or grim figures who, while perhaps on my side of the moral spectrum, were nevertheless prone to a kind of nihilistic cynicism.  My visits to Solstheim fleshed out my picture of the Dunmer, but still, I became accustomed to their overall lack of transcendent idealism.  Therefore, when I first met Ralis at the beginning of Unearthed, I felt comfortable funding his excavation project in spite of his obvious avarice and the distinct possibility that he was skimming off the top; after all, even if he was bilking me out of my gold, he was spending it in an economically depressed area and providing jobs for the locals with money that I would never miss: I was carrying about 120,000 gold at this point and had far more than that in loot at home. 

As the quest haltingly progressed through its stages, I became more concerned about Ralis’s seeming lack of regard for the safety of the miners, but I had little choice other than to provide more funds for the project.  By the final stage, I was in for 11,000 gold, but at least a half-dozen miners and guards had died at the hands of the draugr they awakened.  Of course, when I returned to the project site, saw the additional carnage, and read Ralis’s journals, I realized that Ralis had been slowly possessed by the Dragon Priest Ahzidal.  The truly unnerving part for me was that, unlike other similar possessions in the game, I had actually been speaking with Ralis as he slowly succumbed to Ahzidal’s influence; I had assumed he was just a sociopath.

After defeating the resurrected Ahzidal, I was able to speak with the now clear-headed Ralis about what happened.  Although his memory was clouded by the experience, he was aware that he had killed several of the miners himself as part of the resurrection ritual.  The fact that he was possessed would have exonerated him as far as I was concerned, but he completely failed to show any remorse; instead, he seemed far more interested in making sure that no one ever found out: 

If you choose the dialogue option "I can't let you go unpunished," Ralis flips out, claims that Ahzidal will "command us all" and attacks.  So, you can have a sociopath for a follower, or defend yourself from a raving lunatic.

 Tamriel is a hard place, and people sometimes commit great acts of evil.  Some characters, such as Erandur, are willing to do penance for their crimes, and should be permitted to do so in peace.  Others, such as Sinding and Ralis, lack the appropriate moral horror that should accompany their misdeeds, and therefore deserve punishment commensurate to their sins.  Therefore, the question was not whether I would kill Ralis, but whether I would execute him directly then and there, or gain his trust, then sacrifice him at the Saracellum of Boethiah.  I chose the latter:

• As much as I dislike doing the will of a Daedra, killing someone I would have killed anyway hardly seems like an act of devotion.
•  I also dislike deception, but given the fact that Ralis himself deceived the miners, and that, as a Dunmer, most likely worshiped Boethiah anyway, leading him to sacrifice feels like poetic justice.
• Furthermore, my reward was to hunt down a gang of bandits and kill their leader in order to obtain the Daedric artifact (the Ebony Mail) he was wearing – something I would gladly have done anyway.

Certainly, my decision was a calculated and brutal one, but ultimately a just one as well.  Now that I possess the Ebony Mail (along with several other Daedric artifacts), I can be sure that it will not end up in the wrong hands.