Michael O'Reilly

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Penny O'Reilly

Michael O'Reilly
23 Feb 1962 - 7 Jun 2019
Chi-Town Squares Memorial Panel 3LR


Longtime Chicagoan Michael Francis O'Reilly—a queer artist, activist, Radical Faerie and sometime provocateur best known as Penny—has died at age 57. After surviving decades with HIV, he received a lymphoma diagnosis last autumn; he passed away peacefully June 10, surrounded by friends and family in his Rogers Park home. Born in 1962 in Lansing, Michigan, Penny moved with his parents and four siblings to Wilmette in the early '70s. He attended New Trier East High School, where he was president of the 1980 graduating class. He studied engineering at Rice University in Houston, where he also came out. After college, he lived in Kankakee, Illinois, before settling in Chicago. Penny worked for many years as a phone installer for AT&T, then took an early retirement and worked for himself as a painter, handyman and declutterer.

Those varied professional skills abetted his artistic pursuits. For a 2001 large-scale public-art/activism project, he constructed and painted an enormous canvas with a pro-environment message, which he used to cover an abandoned billboard on Peterson Avenue just west of Ravenswood. Meanwhile, his penchant with telephone technology led to a few occasions of him performing in drag as Ernestine, Lily Tomlin's classic phone-operator character.

In 2002, Penny and his then-partner and dear friend Matthew Gleeman Long bought a home in Rogers Park that the pair envisioned as a small urban sanctuary for faeries. They dubbed it "The Castle," although it's known to most as as the leopard-print house, thanks to Penny's bold animal-print paint job. Penny and Gleeman welcomed dozens of faeries, queers and artists under The Castle's roof—both as permanent residents and as travelers. Some of those wandering through hailed from rural faerie communities in Tennessee and Minnesota, both circles in which Penny was active.

Penny Michael O'Reilly is survived by his siblings, nieces and nephews: sister Camille; sister Eileen, her husband Tom Gerspach and their children Ryan, Megan and Annie; brother Kevin and his son Dylan; and brother Steve, his wife Christine and their sons, Joseph and Eric. ( The middle child of five, Penny often joked that he was "the youngest girl, oldest boy." ) He is also survived by many aunts, uncles, cousins and countless friends.

In his final years and months, Penny found great joy and fellowship in the Queer Contra and Chi-Town Squares dancing groups. The Queer Contra group is dedicating its Saturday, July 27, dance gathering to Penny's memory. All are welcome; details are on Facebook ( at www.facebook.com/events/315922625977629/ ). A private memorial will be held Saturday, Sept. 14.

His family requests that donations can be made in his name to Howard Brown Health Center ( HowardBrown.org/donate/ ), where he long received care.

- Windy City Times, 14 Jul, 2019


I have lots of memories of Penny. Great guy and friend. We read books together and discussed. He was a willing and cheerful worker, always willing and eager to climb 25 foot ladders! Not me.. always smiling, happy, cheerful, never a mean or gossiping word. Truly a good and decent man. I loved dancing with Penny. Had rhythm and knew how to move to music. Excellent dancer. Danced with a certain grace. I miss him already. Gone too soon. — Jeff Hutchins.

Penny was a jewel and I originally met him in 2006, funny, articulate and down right to earth. I feel very blessed and privilege to have known him, may his spirit always be a shining star in our hearts, GOD BLESS YOUR SPIRIT PENNY, SHINE BRIGHT! — Bernard Boynkin

The last time I saw him at a dance he pulled me aside and said “What I wish for you is that you would think less and celebrate more.” — Rebecca Abisdris

Penny was one of the nicest people I know, he will be missed. — Peter Lang

I did not know Penny well, but I remember him as someone always helpful and encouraging to new dancers like myself, helping others to discover the joy he himself found in dancing. — Chris Murray

I'm in total shock. Very sad news. Penny will be dearly missed by everyone who knew him. I'm glad I got the opportunity to know him. — Bobby Poyner

I’m devastated to hear this. Penny was always kind and welcoming to me. I only knew him for a short time but I will miss him greatly. 😞 — Tracy Ruppman

OMG! He was the nicest guy! He will be missed. :-( — Rich Sehnert

He will be missed! He was one of the nicest guys I ever met. — MJ Collins-Ruebensam

I will always remember Penny for his willingness to give a helping hand! Several years ago I was home watching TV and poof, half the house went dark. So out came the extension cords until I could call an electrician. During one of the Thursday night square dances I was lamenting about my electrical problem and Penny said he was an electrician and was willing to come over and take a look. After going room to room he figured out what the problem was, a loose wire in one of the light switches and quickly resolved the problem and poof my house was fully lit up! I was very grateful for his help. Then in April I went I broke my leg skiing he sent me a get well text stating that he would be happy to help me again with getting Rx's groceries or whatever I needed. He was a very sweet man always ready to help. I will miss his friendship, his great Halloween costumes and dancing with him! — Gloria Maile

Penny was always the sweetest dance partner. — Paul Caulfield

A couple of years ago Penny joined my Plus class all the way up in Kenilworth. He took the train up there once a week. Penny was such a wonderful addition to the class. He was an excellent dancer. Explain a call once and he had it. Yet he was always patient with those who needed a little more time. He was just a wonderful presence. I got to tell him how much I admired him about a month ago. He seemed so alive. It was a shock to hear he'd passed away so soon after. The man had courage and kindness. I feel lucky to have known him. — Bruce Holmes

I'm still coming to terms with this loss. But everyone in this picture is smiling . . . and it's because we all got to dance with Penny and laugh with Penny, make delightful fools of ourselves with Penny. Such sweet sadness. — Jack Neiditch