This is a first-time post, so please forgive me if I'm violating any etiquette, or protocols.

I'm playing in a 5e homebrew game. There is a Brothel that I was performing at, but the Madame sold me out to some folks that didn't have my best interests in mind and they tried to kidnap and assassinate my companion. We survived.

So, long story short... We've decided to put her out of business, put her in the poor-house, then buy her brothel and open our own in its place. 

Does anyone have any super-creative ideas on how to put her out of business, without opening a competing business. The idea is to ruin the reputation of the Brothel-Casino and then ruin her name, or drive her mad.

I'm an 8th Level Bard and my Companion is an 8th Level Rogue. We have resources, and decent magic. He is a Forgery Master, and I'm a Magic-heavy Duelist. The DM is very creative and encourages this sort of thing in his games. I want to dismantle her flea-circus and replace it with my own Cirque du Soleil, and we want her alive to see it all, and not be able to do anything to stop it.

We want to hit her with about 4-5 different attacks at once. No bedbugs or lice. We have class.

Any creative, devious, underhanded, or particularly malicious and nasty ideas would be greatly appreciated. Remember the mission is to destroy the trust in the casino, make the brothel undesirable and ruin the Madame's reputation while making her go bankrupt.

If you've read this far, thanks. Looking forward to any ideas.

This seems like a complex undertaking and so we'd probably need more background about the Madame and her establishment for our answers to be useful.

Here are some ideas, rated from classy to not.

1) Find sincere(and well financed) Suitors for the Madame's Best Girls, causing them to pursue family life.

2) Hire a Master Gambler to play the fool and drain the other gamblers and the house for big losses. Be sure to pay for an entourage of personal bodyguards.

3) Pay off undesirable types to gamble, get drunk and generally raise hell in the establishment. Tell them to "pick fights and break stuff". Note: may backfire creating a new hotspot.

4) Bribe someone to take bad food and drink into the food stores. Either really poor quality or stuff that would cause explosive bowel movements.

send rats into the kitchen followed by a health inspector a couple minutes later

Quote from Wtfdndad >>

1) Find sincere(and well financed) Suitors for the Madame's Best Girls 

And/or Boys! :)

This is a very neat little player-driven objective.  I approve.

1.) Do not hire outside people to screw with the brothel.  Not yet.  Instead, investigate the brothel thoroughly, try and find out if it's connected to local mafia/crime guilds.  The Madame needed to know people to sell you out; I recommend finding out who she knows.  That has to be Step 1 - building a picture of the Madame's connections.

2.) Use your connections to start severing her connections.  You're level 8 adventurers with resources and magic - you've got to have some clout.  Offer deals, do some jobs for folks, start cutting the Madame off from her allies.  It'll take some convincing, especially if the brothel is profitable, but if you cut people in on the takeover, offer them some minor concessions or sweetheart rates or the like, you may be able to start isolating the Madame.

3.) Depending on how able you are, infiltrate the Madame's establishment and search for blackmail material she's holding against clients - or even just a client list.  Any documentation proving that Fine, Upstanding Gentlemen of Society are making use of her services.  Releasing that information proves that the Madame cannot be trusted with her client's secrets, which is a blow to her reputation ranging from 'Severe' to 'Fatal'.  Heh, frankly?  Even if you can't find any such documentation, you can manufacture it with your forger.  Have him falsify love letters to the girls from prominent figures that just-so-happen to fall into the wrong hands, or letters offering shady bargains to the Madame in exchange for services rendered.  Be careful there, don't make it too obvious - the people you're framing are canny and experienced, they wouldn't blatantly admit to anything in writing, but you can create letters, notes, and other documents alluding to such bargains with some work and out-of-game discussion and prep.  Circulating those false documents has much the same effect; if the Madame cannot stop you from doing it, then she cannot be trusted to protect her clients' reputations, which is a fatal flaw in her position.

4.) This isn't as classy and is also riskier, but you can potentially use spells that aren't Charm Person to compromise the staff.  Get the bullyboys to look the other way when clients get rough with the girls, get the front attendants to be rude to guests, get the cooks to be sloppy with their cooking, the like.  Sow discontent amongst the brothel's workers, set them against each other, and generally disorder the Madame's house.  This makes her look incompetent and unable to manage even her basic tasks effectively, especially if her girls start getting vocal in their complaints or start refusing to serve certain unpleasant clients.

That's hopefully a start.  Good luck, and be nice to the girls once you've taken over.

I think some necromancy spells, in particular ray of sickness and contagion, when applied at the right times and to the right clients, might really ruin the place’s reputation. 

Thank you for all of the awesome ideas and feedback so far.

As for Madame and her brothel...  The brothel is in the 2nd-quarter of town.  Not shady, and kind of nice actually for a brothel.  The place is large.  Larger and nicer than most of the Inns.  She has over 25 working girls and guys at any given time.  There is also a casino area where mostly card-games are played for high stakes.  Nobles of this city, including a dozen or more of it's princes that are currently competing for the throne after the recent death of their father, frequent the establishment.  She has about a dozen bouncers/ bruisers that work for her and it was one of the more powerful princes that paid assassins to abscond with my companion and attempt to kill him.  That didn't work out well for them, so I'm assuming he will send someone more powerful next time.

The Madam is human, and not of any D&D class.  She has connections with the Thieves Guild, but so does my companion.  She is mainly connected to the Nobles of the city, and they use her place as a social club.  The Brothel isn't viewed as a "House of Ill Repute."  More of a tavern that has live entertainment.

We're definitely going to find out who her supporters, investors, and connections are and work that angle.

We also plan to forge large orders from her suppliers that she can't afford.  We are also going to flier the town with an advertisement for a Card Tournament with a huge prize that she can't afford to lose.  She will either have to risk the loss, or get caught cheating to ensure she wins.  Either way, it should damage her reputation.

But we will absolutely consider all of the above ideas and make sure we hit her with so much at once that she can't react to it all.  Thanks again everyone.  Keep them coming if you have any more.  

Replace her dice/cards with loaded or marked versions. The all it needs is a patron with an ill temper to loose big.

Rumors. That's how. 

I mean, there are more... direct ways of dealing with the matter. But if you want to stay classy, use word of mouth. See chapter 6 of the DMG for the "Sowing Rumors" downtime activity.  It'll take some time and money, but as a bard and a rogue, you should have little problem finding the best places to spread the word that, maybe...

1. The Madame is a spy for the local authorities. All customers are secretly reported to the cops.
2. The Madame viciously beats her employees when they don't earn enough on a given night. 
3. The Madame accepts payment to allow spellcasters to scry on her employees while they are "working". So customers are effectively unwitting pay-per-view actors without their knowledge or consent. 
4. Several of the Madame's employees have been raised from the dead. So the customer may not be the only "stiff" in the room! 
5. The Madame's casino games are rigged. Loaded dice, decks of cards with only 3 Aces, etc. 
6. The burgers may taste good, but that ain't beef! 

Your rogue could forge some shipping invoices showing that the Madame has been receiving large quantities of anti-fungal cream, or maybe some apothecary salves to treat syphilis. And if those invoices accidentally get left on a table at the local tavern... well... oops.

Also - find out where the Madame buys her alcohol. Her supplier must be in cahoots with a theives guild. They all are. Target them! If the booze stops flowing, the business stops growing. 

Have fun!

maybe mass suggestion and/ or geas to persuade customers to leave, then fill the store with stinking cloud

Use pickpocketing and/or illusion spells to make it look like the dealers are cheating in the casino.  Start fires using cantrips (make sure that they're not going to spread too fast- don't want to murder people).  Swipe some (but not all) of the money in her safe, preferably right before the Thieves Guild representative comes to get their cut- make it look like she's trying to cheat the guild.  Use disguise kits and/or magic to come in as different people, lift a few coin purses (or have a  partner do it), then complain that you've been pick pocketed.

 Magic protection is expensive.  This isn't apparently a top-of-the-line, highly exclusive place.  That means that there's a limit to how much they can afford to spend on having mages on duty.  And that means that there will be gaps in their protection.  Find them, exploit them.

Here are some suggestions, rated easiest to most complicated.

1. Go with the rats idea, it will work very well.
2. Put rats/spiders/whatever in the Madame's room (Or even drink)
3. Go for the old-fashion robbery
4. Rumors (Especially with people who know her well.)
5. Hire some fake chefs to put something nasty in the food.
6. Hire fake waiters to put some sort of ooze in the water/sewage pipes.
7. Set up stink bombs around the store (Hired waiters, probably)
8. Go to a morgue/graveyard, take a body, put it in the closet of the casino (When its closed) then, take something special to the owner, make it look like the person was stabbed by the object, then wait until the waiter opens the closet. Then, take them to court. (Litterally)
9. Marry the eldest offspring of Madame, then, when  she meets her "Unexpected demise", you take over the store (Its super evil, so only chaotic evil people)\
10. Build the iron man suit, and...
11. Nevermind.

lawsuit...

True, True.

sue her over unsanitary conditions (it can't be that clean) for starters

I don't see any way to leave her alive to see all this play out that doesn't include her hiring another assassin to make another attempt on your life, and another, and another, ...

Just take her out yourself or have someone else do it and move on.

If you want her to suffer, have her arrested for something and sent of to prison.  Then periodically check in on her condition in prison and reward a few prisoners or guards for screwing with her.  But don't lose track of her cause then she'll hire an assassin, ...

First, assassins cost money.  Typically they cost a lot of money if they're any good at their job.  If you leave her broke and without allies, she's hardly going to have the resources to send infinite assassins after you.

Second, assassins need to know who to go after.  If you're good at covering up your tracks (and better, implicating someone else), the assassins won't be going after you in the first place because she doesn't know that you're the one who did it.

... The Count of Monte Cristo ...

Don't leave her alive.