Our Team

Chris Pappas Owner Chris is a Chicago native and longtime resident of the East Village neighborhood. He has been involved in opening and operating many known hospitality projects throughout Chicago. Prior to The Winchester, he worked as a lead on the operations teams for Mia Francesca, Soul Kitchen, Red Light, Old Town Social, Telegraph, Bluebird, Americano 2211, and Sepia, where his eclectic wine program was recognized as a “Best New Wine List” by Food & Wine in 2008. Chris loves yoga, dogs, motorcycles, vespas, healthy cooking and meditation.

Chris Pappas
Owner

Chris is a Chicago native and longtime resident of the East Village neighborhood. He has been involved in opening and operating many known hospitality projects throughout Chicago. Prior to The Winchester, he worked as a lead on the operations teams for Mia Francesca, Soul Kitchen, Red Light, Old Town Social, Telegraph, Bluebird, Americano 2211, and Sepia, where his eclectic wine program was recognized as a “Best New Wine List” by Food & Wine in 2008. Chris loves yoga, dogs, motorcycles, vespas, healthy cooking and meditation.

Tyler A Hudec Chef Tyler grew up in Northern New Jersey before settling in Chicago. He has spent time in kitchens across Chicago, most recently at Analogue in Logan Square. He spent 2 years in our kitchen as Sous Chef, before becoming our Chef. His food style is New American with Italian and Southern cooking influences. Tyler is a talented musician with 5 active music projects, and a specialization in building and replicating custom and rare synthesizers. He lives in the Ukrainian Village with his fiancée Amanda, and their dog Charlie Garbage.

Tyler A Hudec
Chef

Tyler grew up in Northern New Jersey before settling in Chicago. He has spent time in kitchens across Chicago, most recently at Analogue in Logan Square. He spent 2 years in our kitchen as Sous Chef, before becoming our Chef. His food style is New American with Italian and Southern cooking influences. Tyler is a talented musician with 5 active music projects, and a specialization in building and replicating custom and rare synthesizers. He lives in the Ukrainian Village with his fiancée Amanda, and their dog Charlie Garbage.

Reilly Drew Beverage Director Reilly grew up in the suburbs of Detroit before moving to Chicago. He spent time honing his cocktail chops at the Chicago Athletic Association Hotel and behind our bar before becoming our beverage director. Reilly’s beverage program is focused on unique ingredients taking starring roles in cocktails that skirt the line between classic and contemporary styles. He spends his time outside of work as a professional photographer, music video director, and progressive activist. He lives in Rogers Park with his boyfriend Connor. You can see his work here

Reilly Drew
Beverage Director

Reilly grew up in the suburbs of Detroit before moving to Chicago. He spent time honing his cocktail chops at the Chicago Athletic Association Hotel and behind our bar before becoming our beverage director. Reilly’s beverage program is focused on unique ingredients taking starring roles in cocktails that skirt the line between classic and contemporary styles. He spends his time outside of work as a professional photographer, music video director, and progressive activist. He lives in Rogers Park with his boyfriend Connor.

You can see his work here

 
Ben Montesanto Sous Chef Ben was born and raised in Chicago, now living in the Ukrainian Village. He has spent time in kitchens across Chicago, most recently at Frontier. Ben is inspired by the Italian cooking styles of his grandmother that led him into the kitchen. Ben is an avid sports fan, with a true love for his home team the Cubs! 

Ben Montesanto
Sous Chef

Ben was born and raised in Chicago, now living in the Ukrainian Village. He has spent time in kitchens across Chicago, most recently at Frontier. Ben is inspired by the Italian cooking styles of his grandmother that led him into the kitchen. Ben is an avid sports fan, with a true love for his home team the Cubs! 

Jordan Trammel General Manager & Caffeine Captain Jordan grew up in rural Tennessee before moving to Illinois. Jordan is a passionate coffee expert and  barista extraordinaire, spending time most recently at Wicker Park mainstay Caffe Streets. He operates his own small record label Washed Recordings under which he self-releases. You can listen to his musical creations under the moniker Slow Chapel. Jordan lives in Portage Park with his fiancée Amy and their two dogs.

Jordan Trammel
General Manager & Caffeine Captain

Jordan grew up in rural Tennessee before moving to Illinois. Jordan is a passionate coffee expert and  barista extraordinaire, spending time most recently at Wicker Park mainstay Caffe Streets. He operates his own small record label Washed Recordings under which he self-releases. You can listen to his musical creations under the moniker Slow Chapel. Jordan lives in Portage Park with his fiancée Amy and their two dogs.

Stacia Stitt Parties & Events Coordinator Stacia grew up in Southern California before moving to Chicago. Stacia spends her time away from the Winchester performing as an actor/comedian at various improv, stand up, and theatrical productions across Chicago. Stacia’s dedication to karaoke is unparalleled. She lives in the Ukrainian Village.

Stacia Stitt
Parties & Events Coordinator

Stacia grew up in Southern California before moving to Chicago. Stacia spends her time away from the Winchester performing as an actor/comedian at various improv, stand up, and theatrical productions across Chicago. Stacia’s dedication to karaoke is unparalleled. She lives in the Ukrainian Village.

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