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Series contains materials collected by Al Stewart as part of his involvement with the Halifax-based TightRope leather brotherhood, which was established in the early 1990s, incorporated in 1997, and disbanded in 2007. Series also contains materials related to the Mr. Atlantic Canada Leather [MACLeather] organization, which operated between 1999-2010, and the leather community more broadly. Materials include TightRope administrative and financial records, correspondence, and promotional materials; event cards, flyers, posters, programs, and certificates of participation for TightRope events, MACLeather contests, and leather events across Canada and the United States; photographs of TightRope meet-ups, MACLeather contests, and other leather community events; web print-outs; issues of the Phalia newsletter published by Spearhead leather and denim club in Toronto; erotic gear catalogues; and one copy of the 2002 Men of Pumpjack calendar.

Series contains materials collected as part of Stewart's LGBT advocacy at St John's United Church in Halifax, and his subsequent involvement with Affirm United, an advocacy organization founded in 1982 that supports LGBTQ members of the United Church of Canada. Stewart was involved in the process of achieving Affirmed status for St John's United Church through the Affirming Ministries Program. Series contains articles, essays, and pamphlets regarding homosexuality and religion; informational documents associated with Affirm United and the Affirmation Congregation Program; manuals and other reference materials relating to the operation of Affirmed congregations; correspondence; issues of Consensus, the Affirm United newsletter; and issues of Open Hands, a journal published by Affirmations: United Methodists for Lesbian/Gay Concerns.

File contains one copy of the summer 2000 issue of the AIDS Coalition of Nova Scotia newsletter, featuring an obituary for Al Stewart's friend Wilson Hodder, and one copy of the Nova Scotia HIV/AIDS in the workplace policy enacted 2001-11-16.

File contains notices and flyers for events held by the TightRope Leather Brotherhood, as well as newsletters, correspondence, and event notices from other leather organizations. Materials include copies of the newsletters Smoke Signals, produced by Poconowarriors in Pennsylvania, and The Brand, produced by the Chicago Hellfire Club; correspondence, pamphlets, and registration forms from Spearhead Leather/Denim Social club in Toronto; event notices and registration forms from East Coast Bears, based in Fredricton; correspondence from the Ottawa Knights; one registration form for the Toone Towne event held by Firedancers Texas ; and notices for TightRope events held between May and August, 1999.

File contains five copies of Phalia, the newsletter of the Spearhead Leather/Denim Social Club based in Toronto, published between July, 1999 and July, 2002.