Local Pool Shark Not as Put Together as He Looks

GLENWOOD TAVERN, CHICAGO — Like many bars within the Chicago area, Glenwood Tavern has become a staple of its neighborhood. The space gained notoriety for their craft cocktails and especially for their pool table. On any given day during the week, if you were to look at the pool table, all challengers would likely be playing a single man. Local Pool Shark Cliff Finley is yet to be defeated within the walls of The Glenwood. But despite his cool and calm demeanor on the table. We were surprised to find that Cliff’s home life left something to be desired. Glenwood Bartender Rachel Miller claims she always knew something was off with Cliff. 

“It’s a bold statement to wear a Zoot Suit, in the year 2026. So yeah I didn’t think it was wild to assume that Cliff might be coming here to avoid some stuff. I’m no stranger to it, you work in any bar long enough and you inevitably start to figure out where people keep coming in. I know Cliff looks like a solid guy, with his greased up hair and his feathered cap. But beneath that purple velvet, stands a man that’s been running from something for a long time.” 

After closing our tab, we followed Cliff home from the bar. What we found could not have shocked us more. Despite hustling nearly $800 dollars from unsuspecting patrons at the bar. Cliff retreated to his one bedroom apartment and sobbed for hours. Our correspondent elected to break into Cliff's apartment to get the whole story. After some light grappling, Cliff agreed to give a statement. 

“Fuck…You hope folks will never see you like this. But the fact of the matter is, my life is a wreck. Sure you take one look at me, you see the cigars and the pocket watching sticking out of the neon suit and you think. Hey there’s a guy who's got it all figured out. But no matter how great my life looks from the outside, there’s no hiding the mistakes of the past.” 

Cliff revealed to press that, over the past decade, he had lost nearly a quarter of a million dollars to corner store slot machines. After agreeing to fix the front door, Cliff shared even more with our correspondent. 

“Hustling pool is really just my day job. I go down to The Glenwood at five, hustle pool until 2 AM. Then the real fun starts. Slots are the only true gentlemen's game left out there, and corner store slots are the best of them all. I know what people think, my mother has given me an earful more times than I can count. But most people just don’t get it. It may leave my life in shambles. But for a corner slots man like myself. There’s no other way to live."

At press time, Cliff has been admitted to the emergency room at Saint Frances Hospital. After suffering a near fatal heart attack during hour 18 of his latest corner slot endeavor. The community has come together to support and pray for this unsung hero. In his honor, all gambling city wide will be put on hold Tuesday nights.