I'm working on writing up my homebrew world for my upcoming campaign, specifically working on a Thief/Bandit ring located in a city somewhat similar to Waterdeep in the Forgotten Realms. However, I can't figure out a fun/interesting place to put the central hideout/lair. Any ideas?
So far I've come up with: Sewer Warehouse Tavern ...
So in the starter adventure theres a character who is a member of the zentarim that I always use as the thieves guild contact. She works in the miners guild cataloging claims for the area. The miners guild also serves as the bank for the are so they offer the heroes a safety deposit box for a fee. I bring it up because I like the idea of the guild hiding in plain site. Operating out of businesses that control the flow of cash and influence into town. Another good one may be the city guard, maybe the entire guard or an entire sect of the guard is corrupt and answering to the local thieves guild leader who may or may not also be a member of the guard.
A quaint, little house on a quiet street in a middle-class neighborhood. A couple of the thieves play like they live there to maintain the charade, and there's a tunnel network so the others can come and go unnoticed.
The attic of a church (of a different god). The folks in the main church don't even know they have an attic. Or they're willing to let the thieves do their thing up there for a regular donation.
A cave complex a couple miles outside of town. Just beyond where the city watch tends to patrol.
A rundown old boarding school full of Dodger-like pickpockets and a faculty of thieves.
The catacombs beneath the city.
A portion of the city where no police force has jurisdiction/is paid to go, where all manner of crime happens out in the open, ideally includes an abandoned amusement park.
The hull of a freighter washed ashore outside the city by a hurricane.
"So in the starter adventure theres a character who is a member of the zentarim that I always use as the thieves guild contact. She works in the miners guild cataloging claims for the area. The miners guild also serves as the bank for the are so they offer the heroes a safety deposit box for a fee. I bring it up because I like the idea of the guild hiding in plain site. Operating out of businesses that control the flow of cash and influence into town. Another good one may be the city guard, maybe the entire guard or an entire sect of the guard is corrupt and answering to the local thieves guild leader who may or may not also be a member of the guard."
HALIA!!!!!!! I love Halia!!! She's become a sort of running joke for my friends and I- every campaign I've played in/run she's ended up being involved with some crazy scheme. She's been a vampire, a servant of a lich aspirant, and, in my Saltmarsh campaign that takes place pre-Phandalin, a young Zentarim zealot looking to recruit the characters and eventually run a business in 'that new town east of here'.
As for ideas:
An abandoned tower
The government buildings (with or without the government's knowledge)
Picture a warehouse filled with HUGE wine casks. One of them has a fake front that swings open like a door.
Best part: The wine-makers that own the warehouse are the cover for the whole thing. The guild pays them for the use of the cask and they just keep making wine.
I'm running a campaign right now that has a guild that *may* have influenced the local governmental militia. Works out pretty well.
Rollback Post to RevisionRollBack
“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime.” - Mark Twain - Innocents Abroad
There was an amazing AD&D supplement called Den of Thieves that was describing a Thieve's Guild in details with the hideout underground with access in sewers, taver cellar etc it had street gang ally and rivals, information network of beggars, assassin etc...
I still think the Warehouse is the best because the owners could be simply agreeing to let the Thieves have some space in exchange for letting their products be safe from looting.
A second option I would explore is an abandoned tunnel or tunnel network. The tunnel leads into the basement of one or two craftsmen that allow the thieves access for protection from thievery.
A third option might be in a barn outside of town, or a stable. The stable could be operated nominally as a legitimate business, but the thieves meet in the loft where the hay is stored. The goods are kept in a barn if they become voluminous. Another good companion front for a business is a cooper (barrel maker). The goods are transported in barrels that are sold and taken by wagon to deliver.
As for a thieves guild contact, I have always favored a merchant (for fencing items) or an alchemist (for making potions that thieves would find very helpful).
Good luck and enjoy the game.
Rollback Post to RevisionRollBack
Cum catapultae proscriptae erunt tum soli proscript catapultas habebunt
I still think the Warehouse is the best because the owners could be simply agreeing to let the Thieves have some space in exchange for letting their products be safe from looting.
A second option I would explore is an abandoned tunnel or tunnel network. The tunnel leads into the basement of one or two craftsmen that allow the thieves access for protection from thievery.
A third option might be in a barn outside of town, or a stable. The stable could be operated nominally as a legitimate business, but the thieves meet in the loft where the hay is stored. The goods are kept in a barn if they become voluminous. Another good companion front for a business is a cooper (barrel maker). The goods are transported in barrels that are sold and taken by wagon to deliver.
As for a thieves guild contact, I have always favored a merchant (for fencing items) or an alchemist (for making potions that thieves would find very helpful).
Good luck and enjoy the game.
I have always like the 'if you let us use your basement, we'll see to it that you don't get robbed' idea. You don't even have to stretch the imagination to see this happening.
The corrupt city guard is always good too but I tend to play it so that only SOME are on the take because if they ALL are, someone talks and they all get busted. Same with corrupt officials. You don't need the entire town council or whatever...just one or two.
Does a thieve's guild need an HQ? Maybe they're more of a network spread throughout the city, no one member knows all the others except by certain hand signs or signals, taking jobs from certain contacts and such. Their 'guild hall' is the back room of taverns, dark alleyways, crowded markets, maybe a few wealthy drawing rooms, as befits a shadowy organization. "We are everywhere" they like to say; "you don't find us, we find you."
Does a thieve's guild need an HQ? Maybe they're more of a network spread throughout the city, no one member knows all the others except by certain hand signs or signals, taking jobs from certain contacts and such. Their 'guild hall' is the back room of taverns, dark alleyways, crowded markets, maybe a few wealthy drawing rooms, as befits a shadowy organization. "We are everywhere" they like to say; "you don't find us, we find you."
This.
In my Baldur's Gate, the Thieves Guild frankly, controls an "unofficial" economy that provides common and lower class folk with greater opportunity for prosperity than the structures imposed by the Patriars and the larger merchants who cater to them. Most establishments and businesses in the lower and outer cities keep two sets of books, one for the "legitimate" Baluder's Gate economy and one for the open secret economy. Flaming Fist, the official law and order tool in the Patriar's employ largely looks the other way since if everyone's getting paid things are stable. If factions within the guild get stabby with each other or non members, investigations and enforcement/consequences can happen (though even these are usually negotiated between the guild and the more streetsmart members of the Fist). The Guild also maintains its own banking system apart from the counting houses of the Partriars and larger merchants. Really, if you read about IRL mafias and organized crime syndicates, you'll often see that many of them actually did have a sort of community protection spirit attached to the racket (some legitimate some more extortive), and some members of those communities did in fact benefit. Whether that dynamic works I'm your game depends on how you characterize the "legitimate" authorities in your game world, this structure works really well for a place like Baldur's Gate.
As far as physical infrastructure. The "banks" have sites where business is done, usually the neighborhood Guild captains preferred hang outs, sometimes it's done at the front door, sometimes in a common room in plain view, and then there are certain transactions that happen "in the back." But that's just where the transactions take place, the actual loot is stashed in a system of stash houses no one but people in deep with the guild know much about. More traditional thieves guild business ... discipline sometimes happens "at the front door" or in the street in front of the local captains stoop, sometimes it happens in the back, depends on whether the guild wants to make an example of someone and also admit someone got their goat, or they want a situation to "disappear." Introductions usually happen in more common spaces through discrete conversation, but once it's determined a party is serious about a particular service or endeavor, the talk is taken to the back.
Having a building that basically has a "Thieves Guild" shingle hanging out front probably won't fly, unless your guild has truly corrupted the legitimate powers in the city and can be, and wants to be, that brazen. But a lot of organized crime does eventually try to go "legitimate" and open up legitimate business and markets. Some of that stuff is insulated from the criminal work outside initial start up funds, others allow illicit gains to be mingled into the legitimate economy more easily (some call some aspects of that money laundering).
But if you're talking just a more stereotypical "always up to no good" thieves guild, a sanitation cart. New members have to operate the cart with which they clean the streets of corpses, human and animal waste, etc., higher ups use wherever the cart is as a location to meet, or scout potential marks, it works as a cover because most people will give the cart a wide berth because of the smell. Olfactory camouflage.
I'm working on writing up my homebrew world for my upcoming campaign, specifically working on a Thief/Bandit ring located in a city somewhat similar to Waterdeep in the Forgotten Realms. However, I can't figure out a fun/interesting place to put the central hideout/lair. Any ideas?
So far I've come up with: Sewer Warehouse Tavern ...
Why not all of them? I would go for a warehouse, maybe not one far from the docks. So you have seaside access, town access, easy ways to move cargo in and out and a location where people are always about. Then, have certain locations throughout the city that are connected to tunnels/sewers where people can gain access to the guild HQ. A tavern, a stable, a few booths in the marketplace, a brothel, etc.
I for one LOVE the themes of the boarding school/orphanage where the admin is all thieves guild and the kids get raised up to join the ranks.
.....
In one of my campaigns, early on the PC's were hired to investigate a huge bank heist. No one could figure out how the thieves got in. The PC's eventually figured out there was no robbery at all... a bunch of higher ups at the bank had been stealing for years, but when a noble wanted to build a new castle and tried to withdraw a ton of gold, there wasn't enough to cover it and their embezzlement was going to be exposed. So they faked a break in to explain why all the money was missing.
Players being Players, instead of going to the City Watch, the PCs sold this intel to the thieves guild. Who in turn blackmailed the execs to the point the thieves were basically in charge. So now the thieves guild runs a bank. They moved their people in and that basically became their 'white collar' HQ in the city.
Rollback Post to RevisionRollBack
PC - Ethel - Human - Lvl 4 Necromancer - Undying Dragons * Serge Marshblade - Human - Lvl 5 Eldritch Knight - Hoard of the Dragon Queen
DM -(Homebrew) Heroes of Bardstown *Red Dead Annihilation: ToA *Where the Cold Winds Blow : DoIP * Covetous, Dragonish Thoughts: HotDQ * Red Wine, Black Rose: CoS * Greyhawk: Tides of War
The base doesn't need to be grandiose by any means. It could be an "unmarked building," which is to say one that has no signs hanging out of the front, perhaps no house number or other identifying features. It would take a particularly bored or perceptive character to find this building noticeably unnoticeable. Inside could tell a very different story, where it's full of people not trying to hide their activity because the occupiers just seem to think nobody would bother entering unannounced (leading to a moment of comic silence, before the sudden mad dash to exits, arms, and gathering up loot/evidence), or it could again be very drab, with a family (real or disguised) demanding the party leave their house because they're strangers who have invited themselves in, but up or downstairs tells a very different story.
Perhaps the Thieves' Guild no longer has a central base because its leader is in prison. How many gangs and other operations are run from behind bars, with messages going out with visitors and mail, despite the best efforts (or perhaps not) to decipher messages entering and exiting the place by guards? Perhaps a prison is the safest place for the leader to be, especially one who - for whatever reason - is best kept alive than executed (blackmail, wealth, a dead man's switch to something dangerous)? They have guards, regular meals, and are probably in a tactically secure location. Or maybe the leader was quietly executed, and someone unbenownst to the guild is calling the shots from within.
The final idea I can think of is where their base isn't. Red herrings and misinformation will become aggrevating to the players rather than just their characters if used in overabundance, but you could also give your magic users something to do with detecting illusions hiding secret entrances to spice things up. An alleyway concealed by an illusory wall, or building, or whatever you wish to put in plain sight should be an obstacle that also sets the tone for a well prepared Thieves' Guild that really doesn't want to be found.
I hope those ideas help, and do continue to consider the excellent ideas mentioned by others here! Best of luck in whatever you decide on!
Zero is the most important number in D&D: Session Zero sets the boundaries and the tone; Rule Zero dictates the Dungeon Master (DM) is the final arbiter; and Zero D&D is better than Bad D&D.
"Let us speak plainly now, and in earnest, for words mean little without the weight of conviction."
So far people have offered variations of secrecy. Someplace clandestine to avoid the law. Maybe even hiding in the space between the laws.
There’s also the option of ripping off John Wick. Before you dismiss that out of hand - it’s pretty easy to follow, which means less prep for you; and it’s pretty awesome. Just pretend the law isn’t even there. Completely abandon realism. It’s fantasy, go nuts.
Whatever you make it, though, you should make it the kind of place that the characters don’t go to very often. The actual HQ of the Thieves Guild (!) should always be an impressive location because it’s usually going to only show up at an important story beat. The start of your rogue’s career; the time your paladin has to compromise in the face of an even greater foe; the time your monk has to beat the hell out of the thugs that burned down his dads restaurant, whatever.
I dunno, I think Officer Jimmy would behave exactly as a Flaming Fist officer would in Baldur's Gate if a noise complaint near the upper city turned out to be Thieves Guild business.
The thing is, now I've only seen Wick 1 + 3, in the Wickverse, there are cops, there is a muggle world where spectacular gun fu skill sets aren't seen. The Wick World is a shadow world, and a glamorization of how underworlds like to think of themselves. It's just the system the "legitimate authorities" serve and the ones the "thieves guild" serve are so detached from each other they might as well be parallel universes. Sure you see weird things happening from the other side every now and then, but you're in one world or the other, rarely both, and things only get bad when they have to collide.
I mean on a more comic level the Pirates of the Caribbean franchise operates on a similar principle, there's the various official empires but also a very rich counter world with its own codes and traditions and culture ... it's sort of literally based in the word outlaw.
I'm working on writing up my homebrew world for my upcoming campaign, specifically working on a Thief/Bandit ring located in a city somewhat similar to Waterdeep in the Forgotten Realms. However, I can't figure out a fun/interesting place to put the central hideout/lair. Any ideas?
So far I've come up with:
Sewer
Warehouse
Tavern
...
So in the starter adventure theres a character who is a member of the zentarim that I always use as the thieves guild contact. She works in the miners guild cataloging claims for the area. The miners guild also serves as the bank for the are so they offer the heroes a safety deposit box for a fee. I bring it up because I like the idea of the guild hiding in plain site. Operating out of businesses that control the flow of cash and influence into town. Another good one may be the city guard, maybe the entire guard or an entire sect of the guard is corrupt and answering to the local thieves guild leader who may or may not also be a member of the guard.
A quaint, little house on a quiet street in a middle-class neighborhood. A couple of the thieves play like they live there to maintain the charade, and there's a tunnel network so the others can come and go unnoticed.
The attic of a church (of a different god). The folks in the main church don't even know they have an attic. Or they're willing to let the thieves do their thing up there for a regular donation.
A cave complex a couple miles outside of town. Just beyond where the city watch tends to patrol.
A rundown old boarding school full of Dodger-like pickpockets and a faculty of thieves.
The catacombs beneath the city.
A portion of the city where no police force has jurisdiction/is paid to go, where all manner of crime happens out in the open, ideally includes an abandoned amusement park.
The hull of a freighter washed ashore outside the city by a hurricane.
"So in the starter adventure theres a character who is a member of the zentarim that I always use as the thieves guild contact. She works in the miners guild cataloging claims for the area. The miners guild also serves as the bank for the are so they offer the heroes a safety deposit box for a fee. I bring it up because I like the idea of the guild hiding in plain site. Operating out of businesses that control the flow of cash and influence into town. Another good one may be the city guard, maybe the entire guard or an entire sect of the guard is corrupt and answering to the local thieves guild leader who may or may not also be a member of the guard."
HALIA!!!!!!! I love Halia!!! She's become a sort of running joke for my friends and I- every campaign I've played in/run she's ended up being involved with some crazy scheme. She's been a vampire, a servant of a lich aspirant, and, in my Saltmarsh campaign that takes place pre-Phandalin, a young Zentarim zealot looking to recruit the characters and eventually run a business in 'that new town east of here'.
As for ideas:
An abandoned tower
The government buildings (with or without the government's knowledge)
A nearby mine that is 'haunted'
Only spilt the party if you see something shiny.
Ariendela Sneakerson, Half-elf Rogue (8); Harmony Wolfsbane, Tiefling Bard (10); Agnomally, Gnomish Sorcerer (3); Breeze, Tabaxi Monk (8); Grace, Dragonborn Barbarian (7); DM, Homebrew- The Sequestered Lands/Underwater Explorers; Candlekeep
Picture a warehouse filled with HUGE wine casks. One of them has a fake front that swings open like a door.
Best part: The wine-makers that own the warehouse are the cover for the whole thing. The guild pays them for the use of the cask and they just keep making wine.
I vote for City Guard.
I'm running a campaign right now that has a guild that *may* have influenced the local governmental militia. Works out pretty well.
“Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime.” - Mark Twain - Innocents Abroad
There was an amazing AD&D supplement called Den of Thieves that was describing a Thieve's Guild in details with the hideout underground with access in sewers, taver cellar etc it had street gang ally and rivals, information network of beggars, assassin etc...
Wow! A lot of great stuff here, I will definitely be using some of these ideas. Thank you to all!
I still think the Warehouse is the best because the owners could be simply agreeing to let the Thieves have some space in exchange for letting their products be safe from looting.
A second option I would explore is an abandoned tunnel or tunnel network. The tunnel leads into the basement of one or two craftsmen that allow the thieves access for protection from thievery.
A third option might be in a barn outside of town, or a stable. The stable could be operated nominally as a legitimate business, but the thieves meet in the loft where the hay is stored. The goods are kept in a barn if they become voluminous. Another good companion front for a business is a cooper (barrel maker). The goods are transported in barrels that are sold and taken by wagon to deliver.
As for a thieves guild contact, I have always favored a merchant (for fencing items) or an alchemist (for making potions that thieves would find very helpful).
Good luck and enjoy the game.
Cum catapultae proscriptae erunt tum soli proscript catapultas habebunt
I have always like the 'if you let us use your basement, we'll see to it that you don't get robbed' idea. You don't even have to stretch the imagination to see this happening.
The corrupt city guard is always good too but I tend to play it so that only SOME are on the take because if they ALL are, someone talks and they all get busted. Same with corrupt officials. You don't need the entire town council or whatever...just one or two.
Does a thieve's guild need an HQ? Maybe they're more of a network spread throughout the city, no one member knows all the others except by certain hand signs or signals, taking jobs from certain contacts and such. Their 'guild hall' is the back room of taverns, dark alleyways, crowded markets, maybe a few wealthy drawing rooms, as befits a shadowy organization. "We are everywhere" they like to say; "you don't find us, we find you."
This.
In my Baldur's Gate, the Thieves Guild frankly, controls an "unofficial" economy that provides common and lower class folk with greater opportunity for prosperity than the structures imposed by the Patriars and the larger merchants who cater to them. Most establishments and businesses in the lower and outer cities keep two sets of books, one for the "legitimate" Baluder's Gate economy and one for the open secret economy. Flaming Fist, the official law and order tool in the Patriar's employ largely looks the other way since if everyone's getting paid things are stable. If factions within the guild get stabby with each other or non members, investigations and enforcement/consequences can happen (though even these are usually negotiated between the guild and the more streetsmart members of the Fist). The Guild also maintains its own banking system apart from the counting houses of the Partriars and larger merchants. Really, if you read about IRL mafias and organized crime syndicates, you'll often see that many of them actually did have a sort of community protection spirit attached to the racket (some legitimate some more extortive), and some members of those communities did in fact benefit. Whether that dynamic works I'm your game depends on how you characterize the "legitimate" authorities in your game world, this structure works really well for a place like Baldur's Gate.
As far as physical infrastructure. The "banks" have sites where business is done, usually the neighborhood Guild captains preferred hang outs, sometimes it's done at the front door, sometimes in a common room in plain view, and then there are certain transactions that happen "in the back." But that's just where the transactions take place, the actual loot is stashed in a system of stash houses no one but people in deep with the guild know much about. More traditional thieves guild business ... discipline sometimes happens "at the front door" or in the street in front of the local captains stoop, sometimes it happens in the back, depends on whether the guild wants to make an example of someone and also admit someone got their goat, or they want a situation to "disappear." Introductions usually happen in more common spaces through discrete conversation, but once it's determined a party is serious about a particular service or endeavor, the talk is taken to the back.
Having a building that basically has a "Thieves Guild" shingle hanging out front probably won't fly, unless your guild has truly corrupted the legitimate powers in the city and can be, and wants to be, that brazen. But a lot of organized crime does eventually try to go "legitimate" and open up legitimate business and markets. Some of that stuff is insulated from the criminal work outside initial start up funds, others allow illicit gains to be mingled into the legitimate economy more easily (some call some aspects of that money laundering).
But if you're talking just a more stereotypical "always up to no good" thieves guild, a sanitation cart. New members have to operate the cart with which they clean the streets of corpses, human and animal waste, etc., higher ups use wherever the cart is as a location to meet, or scout potential marks, it works as a cover because most people will give the cart a wide berth because of the smell. Olfactory camouflage.
Jander Sunstar is the thinking person's Drizzt, fight me.
Why not all of them? I would go for a warehouse, maybe not one far from the docks. So you have seaside access, town access, easy ways to move cargo in and out and a location where people are always about. Then, have certain locations throughout the city that are connected to tunnels/sewers where people can gain access to the guild HQ. A tavern, a stable, a few booths in the marketplace, a brothel, etc.
I for one LOVE the themes of the boarding school/orphanage where the admin is all thieves guild and the kids get raised up to join the ranks.
.....
In one of my campaigns, early on the PC's were hired to investigate a huge bank heist. No one could figure out how the thieves got in. The PC's eventually figured out there was no robbery at all... a bunch of higher ups at the bank had been stealing for years, but when a noble wanted to build a new castle and tried to withdraw a ton of gold, there wasn't enough to cover it and their embezzlement was going to be exposed. So they faked a break in to explain why all the money was missing.
Players being Players, instead of going to the City Watch, the PCs sold this intel to the thieves guild. Who in turn blackmailed the execs to the point the thieves were basically in charge. So now the thieves guild runs a bank. They moved their people in and that basically became their 'white collar' HQ in the city.
PC - Ethel - Human - Lvl 4 Necromancer - Undying Dragons * Serge Marshblade - Human - Lvl 5 Eldritch Knight - Hoard of the Dragon Queen
DM - (Homebrew) Heroes of Bardstown * Red Dead Annihilation: ToA * Where the Cold Winds Blow : DoIP * Covetous, Dragonish Thoughts: HotDQ * Red Wine, Black Rose: CoS * Greyhawk: Tides of War
The base doesn't need to be grandiose by any means. It could be an "unmarked building," which is to say one that has no signs hanging out of the front, perhaps no house number or other identifying features. It would take a particularly bored or perceptive character to find this building noticeably unnoticeable. Inside could tell a very different story, where it's full of people not trying to hide their activity because the occupiers just seem to think nobody would bother entering unannounced (leading to a moment of comic silence, before the sudden mad dash to exits, arms, and gathering up loot/evidence), or it could again be very drab, with a family (real or disguised) demanding the party leave their house because they're strangers who have invited themselves in, but up or downstairs tells a very different story.
Perhaps the Thieves' Guild no longer has a central base because its leader is in prison. How many gangs and other operations are run from behind bars, with messages going out with visitors and mail, despite the best efforts (or perhaps not) to decipher messages entering and exiting the place by guards? Perhaps a prison is the safest place for the leader to be, especially one who - for whatever reason - is best kept alive than executed (blackmail, wealth, a dead man's switch to something dangerous)? They have guards, regular meals, and are probably in a tactically secure location. Or maybe the leader was quietly executed, and someone unbenownst to the guild is calling the shots from within.
The final idea I can think of is where their base isn't. Red herrings and misinformation will become aggrevating to the players rather than just their characters if used in overabundance, but you could also give your magic users something to do with detecting illusions hiding secret entrances to spice things up. An alleyway concealed by an illusory wall, or building, or whatever you wish to put in plain sight should be an obstacle that also sets the tone for a well prepared Thieves' Guild that really doesn't want to be found.
I hope those ideas help, and do continue to consider the excellent ideas mentioned by others here! Best of luck in whatever you decide on!
Zero is the most important number in D&D: Session Zero sets the boundaries and the tone; Rule Zero dictates the Dungeon Master (DM) is the final arbiter; and Zero D&D is better than Bad D&D.
"Let us speak plainly now, and in earnest, for words mean little without the weight of conviction."
- The Assemblage of Houses, World of Warcraft
Now, there is another way of doing this entirely:
So far people have offered variations of secrecy. Someplace clandestine to avoid the law. Maybe even hiding in the space between the laws.
There’s also the option of ripping off John Wick. Before you dismiss that out of hand - it’s pretty easy to follow, which means less prep for you; and it’s pretty awesome. Just pretend the law isn’t even there. Completely abandon realism. It’s fantasy, go nuts.
Whatever you make it, though, you should make it the kind of place that the characters don’t go to very often. The actual HQ of the Thieves Guild (!) should always be an impressive location because it’s usually going to only show up at an important story beat. The start of your rogue’s career; the time your paladin has to compromise in the face of an even greater foe; the time your monk has to beat the hell out of the thugs that burned down his dads restaurant, whatever.
I dunno, I think Officer Jimmy would behave exactly as a Flaming Fist officer would in Baldur's Gate if a noise complaint near the upper city turned out to be Thieves Guild business.
The thing is, now I've only seen Wick 1 + 3, in the Wickverse, there are cops, there is a muggle world where spectacular gun fu skill sets aren't seen. The Wick World is a shadow world, and a glamorization of how underworlds like to think of themselves. It's just the system the "legitimate authorities" serve and the ones the "thieves guild" serve are so detached from each other they might as well be parallel universes. Sure you see weird things happening from the other side every now and then, but you're in one world or the other, rarely both, and things only get bad when they have to collide.
I mean on a more comic level the Pirates of the Caribbean franchise operates on a similar principle, there's the various official empires but also a very rich counter world with its own codes and traditions and culture ... it's sort of literally based in the word outlaw.
Jander Sunstar is the thinking person's Drizzt, fight me.