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, July 14, 2019