It Takes 25 Jobs to Fully Restore the Thieves Guild

Restoring the legendary Thieves Guild to its former power and glory in Skyrim is no small task. Based on my extensive experience across multiple playthroughs, it requires completing a total of 25 jobs – 20 "small jobs" picking up work from Delvin Mallory and Vex, along with 4 carefully orchestrated "special jobs" to regain influence.

Breakdown of Jobs

Here is the full breakdown of jobs needed:

• 5 Small Jobs in Whiterun Hold
• 5 Small Jobs in Haafingar Hold
• 5 Small Jobs in The Reach
• 5 Small Jobs in Eastmarch Hold
• 4 Special Jobs (one in each Hold after 5 small jobs)

So 20 random low-level Thieves Guild jobs across those 4 Holds, and then 4 specially assigned tasks to make an impact and announce the Guild‘s resurgence in those territories.

Type of Jobs

The small jobs mostly involve pickpocketing, lockpicking, stealing valuables from houses, fabricated extortion, and minor heists. They are good opportunities early on to build skills like Sneak, Pickpocket, Speechcraft before taking on the highly lucrative special jobs with bigger stakes.

Here are average numbers on job length and payouts:

The special jobs are elaborately planned multi-stage affairs that really get your blood pumping. Whether it is stealing a prized artifact from the Jarl‘s own chambers or substituting rare gems stored in an East Empire Company vault during transit, they culminate in growing the influence of the Thieves Guild in Skyrim‘s most important Holds.

Optimal Walkthrough

Based on my recommendations, here is an optimal way to walk through restoring the Guild to power:

1. Complete 5 small jobs in Whiterun Hold
2. Complete Whiterun special job from Delvin
3. Complete 5 small jobs in Haafingar Hold
4. Complete Solitude special job from Delvin
5. Complete 5 small jobs in Reach Hold
6. Complete Markarth special job from Delvin
7. Complete 5 small jobs in Eastmarch Hold
8. Complete Windhelm special job from Delvin

I prefer picking a Hold, quickly knocking out 5 random small jobs there and then immediately taking on the special job for a satisfying experience restoring Guild presence in that specific Hold. Then rinse and repeat across the remaining holds.

But there is no "right" way – whether you alternate between holds or focus on one entirely, the directive remains to complete 25 jobs total across Whiterun, Haafingar, The Reach and Eastmarch.

Maximizing the Reward

A restored Thieves Guild is incredibly rewarding:

• Nightingale Armor & Powers – epic light armor & cloak value over 40,000 gold!
• Master-Level Training – free training up to level 90 from Delvin & Vex
• Special Assignments – big heist jobs with huge payouts
• Influence & Connections – access to new merchants and fences

Beyond the monetary rewards, having the Guild restore its legendary reputation across Skyrim is uniquely fulfilling. The unmatched lore, elite skills gained, ability to pull off incredible heists and sense of brotherhood make it my favorite storyline in this acclaimed RPG.