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Predicting Which Chicago Neighborhood Each Barstool Employee Will Be Moving To

Pedro Lastra. Unsplash Images.

The big Barstool Sports New York to Chicago move is upon us with a number of folks ready to hit the Oregon Trail as soon as June so I figured why not play a little game of neighborhood prediction before they come.

Big Cat

Neighborhood - xxxx N. Noble

Big Cat is one of the people where I know which neighborhood he'll be living in and it felt like kind of cheating to put it down so I just went with the new office's address. Plus I'm sure he doesn't want people screaming "Suck my dick, Lenny!" at him as he takes Stella and the kids on their walks too.

He'll also basically be living at the office anyways because the man grinds.

Wicker Park

PFT is a multifaceted man so I think Wicker fits best. He can go let his hair down and be Ska/Pup Punk PFT at one of those bars on Milwaukee. Then he can put the bun up and watch a game on Division street. Plus I heard a rumor that 'Exit' is supposed to be coming back soon (it's borderline Old Town, whatever) and while I know PFT isn't necessarily one of those people who drinks blood on the second floor I do think he'd be down to hang out with the people who drink blood just to see what it's all about.


It's safe to say that there won't be as sharp of a change of scenery on this list quite like Uncle Chaps going from the Lone Star State to the land of Darren Rovells, but I know it's a change Chaps would sure as hell be excited for. The Texas heat to the lake front breeze. Tex Mex to Buffalo Joes. The Cons to the Libs.

I'd give our Purple Heartsman one full Winter here before he starts being a head honcho on the D streets shoveling all the driveways out while his glasses fog up, but still being as happy as a clam just to be in Illinois.


Good old Philly Kate and Canaryville are a match made in heaven by herself. Then you toss in 'The Beav' plus a couple kids running around and we'll have ourselves a Shameless reboot with Kate schilling her world famous Spaghetti-O's at Kelly's Tavern in no time.


I have zero basis for saying that Donny would be good for Andersonville, but Little Bad Wolf is there and Donny makes a great smash burger so that's what I landed on.

Gold Coast

Ah, Corporate Hank.

The elite businessman of the bunch has to live where the other elite businessmen live. He'll be taking shits in JB Pritzker's gold toilets and walking around the Viagra Triangle with a hot blonde he plucked from the Playpen in no time.

Jefferson Park

Blue Collar JJ is perfect for a neighborhood like Jefferson Park because while it is blue collar it still has some rough around the edges places where if Jerry was in a pinch he could shit his pants and nobody would bat an eye.

Old Town

Kyle's kind of a tough one to peg. I chose Old Town for the simple thought of how much he'd be seething every time he walked past Fireplace or Benchmark to see the line 50 people deep of 25 year olds. I don't know why this would make Kyle seeth, but the thought of it makes me laugh so here we are. The other option that popped into my head for some reason was Oak Park so he could be an assistant wrestling coach at OPRF. Power program. (No disrespect to Grant)


Simply put, when I think of the most "country" surrounding suburb I think of Kankakee. I know it's probably too far out to even be considered a Chicago suburb, but Bishop Mac used to be in the CCL and that's how I count borders dammit. Speaking of Bishop Mac you can set an easy lock that Tommy Walker would be donning that green and be the starting free safety for the Fightin' Irish if the Walkers stay in Illinois that long. Another added bonus is that it's already a nice head start for a quick trip (8.5 hours) back to Tupelo, MS. Brandon will have a quick stop off at the Marion, IL Taco Johns then be there before he knows it on the same tank of gas.


The Makin' Money's are great people. They love to have a good time, but even more so they love to gamble. Find yourself at any event with Mr. Makin Money and he won't only be guzzling down some whiskey he'll also be challenging you to a $500 Paper, Scissors, Rock game. At the end of the day though we only support responsible gambling here so I chalked the Makin Money's down for Aurora so they can legally gamble at Hollywood Aurora as well as take the kids for a little special treat at the Aurora Outlet Mall which is low key pretty damn good.

Ukrainian Village

Nothing more to add. Respect.

Mount Greenwood

Spider gets shit done. He does some dirty jobs for this company and he could use a nice union working neighbor to give him recommendations on where to buy the most comfortable pair of work boots in the city. That's where Mount Greenwood thrives. In exchange our guy Spider would be getting everybody a carton of Reds in their stocking come Christmas time and share all of the Miller Lites from his cooler at Papa Hops in the Summer.

Terminal 5 (O'Hare)

Chinatown was the easy answer, but there was a Chinatown in New York and Donnie didn't live there so I didn't go with it. I suppose this answer is also cheap, but don't tempt Donnie with an outrageous content idea. All it would take is for someone to challenge him to replay the Tom Hanks 'Terminal' movie and he'd have his selfie stick, a termie, and be sleeping on his rollie bag in a millisecond.


WSD gets himself some back up to knock Jerry Reinsdorf off of his iron throne on the south side. Dave ain't gonna do the dirty work anymore. He's too busy living in ritzy Lincoln Park, drinking vodka sodas at Halligan's to be on the front lines where he is needed most. That's where Zah will step in to look out for White Sox kingdom while picking up a generous 15% discount at Phil's Pizza for his troubles.



Barstool River North

No mattress or pillow needed. Give this man his laptop, a bottle of Pink Whitney, and Stool Scenes playing on loop and he'll be as happy as a pig in shit.