The boss needed a place to spend when he would be in other cities, and since Chicago was one of the largest and most influential of all 1950s crime, it only made sense that this would be the first that he would explore options. Perhaps there was a nice condo or a family homestead where he could take refuge during those windy summer days. 

"What have you scoped out for me?"

A few photographs were set on the table in front of the boss, most of them unassuming and just standard fare. There were quite a few intricate homes in the Chicago suburbs, but the one that caught his eye the most was the one with dozens of windows-- it was huge, and it was clearly somewhere that any reputable businessman would be able to call his home.

"Tell me more about that one..."

"Well, it's expensive and large. The last family moved out to go to the countryside and they're taking their time getting rid of it, they want full price."

"Very well. Give it to them."

Once the transaction was made, the boss made his way to this extremely extravagant and fully furnished Mansion that he had just bought, it was the largest mansion by far and extremely impressive: all other mansions in Chicago looked almost pedestrian, which is exactly why he had to have it in the first place.

Too bad he'd only spend a few days in Chicago per year, but that was a problem for another time, I suppose.

"Let's host my first annual Biggest Mansion in Chicago Party."

and so it began, the largest party in the largest mansion, where thousands of the most influential figures in all of the mob would arrive in style to enjoy the festivities. There would even be a cheese fountain, which is a pretty big deal in most cheese-related circles, of which the midwest had a lot.

Welcome to the biggest mansion in all of Chicago! Enjoy.

What's the square footage?

Nice try, Dwigt. The last time I gave away how large my largest mansion was, someone quickly had one built with a single extra inch of space in the garage, which quite frankly shouldn't have counted. Garages should NOT be considered when speaking about how large a house is, it wasn't even INSIDE of the house. Give them a few extra acres of property, sure, but don't come telling me that my mansion is now the second largest and that I will no longer be awarded the plaque of "Largest Mansion in Rhode Island."

Fucking politics. Anyways, to answer your question: No, I will not answer your question.

Rhys heard that TheBoss had bought a new mansion in Chicago. Tired of crappy motels and hovels, Rhys decided to live there.

One night, he packed his bags and made his way to the mansion. It was huge. He sneaked in and found an empty room with the most comfy bed in the universe. The room was a little ways away from movement so nobody would notice that he was squatting.

He unpacked his bags, put his clothes in the closed (also the ones he was wearing) and started roasting some meat on the fireplace. Rhys liked his new home.

Craven had heard about the purchases of a large mansion in the great city of Chicago. One of his favourite cities to visit in his limited spare time. Upon arriving at the mansion, it was true what he had heard, it was massive!

Taking in the surroundings, he spent a little while trying to decide if this was indeed as claimed, the biggest mansion in Rhode Island. After a short while the decision was made... 

"Without a doubt, this mansion is one inch bigger than the last claimed biggest mansion in Rhode Island"

Indifference was floating around in the gangster circles looking for something that looked fun.

A mansion in Chicago?  Fuck yeah.  Let's do it.

Indifference packed up his bags and then took the flight to (where were we going?) Chicago.  Who gives a fuck.  Indifference certainly didn't.

He arrived with his bags and went straight to the basement. 

It's not bigger, it's not. I spent so much money and effort in attempting to make sure that I had to largest mansion in Chicago, I went to many different carpenters and had them measure this house from its basement all the way to the attic, and there was absolutely no way that I did not get the biggest fucking place in this damn city.

You're getting very close to having a court case brought up against you for slanderous accusations. I'm a businessman and a boss. I take my business and bossery both extremely and equally seriously. The only saving grace you have is that I recently fired all of my lawyers for being unable to keep me from false imprisonment, I did not attempt to pickpocket that person and these pieces of shit couldn't get me off the hook, so for now I am on my own.

Only me and my two bodyguards, both of which I had to save from false imprisonment too if you could believe it. Now, if you will excuse me, I am kindly asking you to leave my extremely large Mansion-- the BIGGEST mansion. If you do not, then I am afraid that I'll have to call my bodyguards on you.

Let's not make a scene, Dwigt. 

Rhys invited over some of his friends and threw a party in his new room. Thankfully the mansion was so big that the noise didn't reach TheBoss's ears.

Everything was going well, they were dancing and smoking crack when suddenly Rhys' STUPID bodyguard called AAAAAA (that was his nickname) decided to raid the kitchen. He was so crazy on drugs that Rhys was sure he would be noticed.

With his new Louisville slugger that he bought from HATS AND BATS he hits AAAAAA in the head.

"AAAAAA" Screamed AAAAAA in pain. Rhys continued to beat the man mercilessly. The party was over.

After cleaning the blood of the bodyguard from the carpet, Rhys went to sleep. He had sweet dreams.

Waking up in the middle of the night, he was hungry as fuck but he couldn't risk getting discovered. So he had a crazy idea. Do it anyway.

Sneakily moving from furniture to furniture, Rhys made his way to the kitchen. The mansion keepers were sleeping so it was easy. With his mouth watering, he opened the fridge. To his surprise, it was empty.

He returned to his room and grabbed his Louisville slugger and went to the kitchen to teach that fridge a lesson it wouldn't forget.

Hit after hit the fridge finally broke down after two minutes of violence. A light was turned on in the room next to the kitchen so Rhys fled the scene but not before leaving a note inside the fridge.

FUCK YOU THE BOSS 

TheBoss I am sorry does matter how big your Mansion is. It depends on how much spend living in it. Just because you want to make look like you are the biggest mine has been here for years and you built yours lol Mine was my ancestor when she was a Crew Leader here, That's how you should get your Mansion.

MarissaVixen, you have a lovely mansion. Honestly, and I mean it from the bottom of my heart that you have one of the largest Mansions in all of Chicago. Mine's just bigger, and has an entire pool in the basement, if anyone would like to go check it out-- you're free to do so. As far as Rhys and @Dwigt_K_Schrute, I do not care about any of that.

You're both just trying to upset me and you know what? It's working. I do care about it. I care so fucking much and I really want both of you to stop being so mean before I blow a fucking gasket. This is NOT your personal play house and this is NOT up for debate: So, the next person to make a malarky in this house will be subjected to my two most powerful weapons, the Boss punches his fists together.

These bad boys, right here.

Rhys was hiding in the shadows when he heard TheBoss' speech. The only thing he could understand out of all of that was "entire pool in the basement".

He made his way to the place and found the pool. He jumped in and started peeing. Also he didn't took a shower for nearly two weeks. That pool was now very NASTY.

"That'll teach 'em. And they'll never suspect a thing." 

Rhys thought about taking a shit in the pool, but he wasn't a savage barbarian. He left the scene and sneaked back to him room.

BIGGEST MANSION IN CHICAGO PARTY

WHEN: RIGHT FUCKING NOW!!!

Now that everything was ready, The Boss decided that he would start up the big party in what was known by everyone as the most influential place to be in any city in all of America. Surely, the man who invented the idea business would be able to think up something that would rival that of any common house affair.

We're not just having one cake, but two. No, three. Three entire cakes for this event. One chocolate, another one that's chocolate, and a third that's made entirely of rose petals. Ever heard of it? Neither had I until someone told me the price was exorbitant and I immediately had to have it. Same with those nine sculptures of ducks sitting around the premises, every duck with its own personality. My favorite is the one smoking a cigar and wearing glasses, but maybe you'll enjoy the duck holding a book: There's a duck for everyone here!

The finishing touches were placed on the house, and the pool was completely emptied and cleaned before anyone showed up, for no particular reason, but now it was completely clean and largely piss-free. Please do not be afraid of the pool having any piss in it. I cannot stress how little pee there is in this pool.

Cars will be parked by my very own butler, just make sure that you get your keys back later. He will keep them. He might eat them. I can't prove that he has been eating keys, but just to be safe NEVER leave him alone with your keys for too many hours, try picking them up as soon as you possibly can. Thank you!

There was nothing else left to do at this point, everything was set out, including the hors d'oeuvres which were mostly just little pickles and sausages and a lot of really little food items placed on toothpicks and lined up in neat rows. There were dozens of these things, and the boss's favorite was the gherkins. Even smaller than a regular pickle, but just as flavorful. Yum.

Also, if you see a weird guy who says he lives in my walls, please just tell him to move along. That's just Rhys, and in Detroit, he is a very powerful man, but I guess in Chicago he likes to live in people's mansions and eat all of their food. I think he may have gotten rabies on his last trip here, I'm worried for him.

If you find him, let him know people in Detroit are looking for him. It has been days since they've seen him last. They're beginning to worry.

Moving through the walls of TheBoss' mansion, Rhys waited for the perfect opportunity to ambush the man and end his miserable life. After minutes of staying still and barely making any noise, he finally saw his victim. White hat and white suit. Rhys made his way to the closet where he exits the wall and grabs his trusty Louisville slugger.

With a smile on his face, he rushes towards TheBoss and hits him straight on the head. The man falls on his knees and Rhys continues to beat him. After that, he pulled his revolver and shot him three times. Also bitch-slapped him for good measure, but when he grabbed TheBoss to bitch slap him across the face, he noticed it was a DECOY. IT WAS NOT THE REAL BOSS.

"Nothing to see here..." Rhys said, his voice cracking and tears falling down. He made his way back to the closet and made his way to his room through the walls.

After crying in his room for a few minutes, he had a great idea. To beat up another person, this time the butler. He left the mansion by the window and ran towards the garage where the butler was parking the car.

Rhys and the butler's eyes meet and they stare at each other. Rhys charges.

"WHAT ARE YOU DOING?!" The butler could not believe his eyes, with the speed of a cheetah Rhys closes the distance and delivers a POWERFUL DROPKICK to the butler's face and stole his clothes. Rhys was now the butler.