In the early evening of April 12, Trident International Windy City and Leather Archives and Museum presented the 13th Annual Trident Cupcake Wars.
The event raises funds for Howard Brown Health’s Broadway Youth Center and serves each year as a traditional social gathering for LGBTQ+ members of the leather, kink and fetish community. The 2026 edition was loaded with surprises, exotic cupcakes and a touch of ribald naughtiness as seven organizations competed to raise cash and nab the title of Master Baker.
Among the contestants this year was ONYX, represented with a double chocolate cupcake with vanilla and chocolate frosting; Chicago Hellfire Club, with a chocolate and coffee cake topped with machismo cherries and “a salty surprise”); and Mr. Chicago Leather, who presented a “Leather Boy Cupcake”—a dark chocolate cake topped with green peppermint frosting with a white chocolate drizzle.
Other contestants included Illinois Gay Rodeo Association, with a key lime cupcake; Chicago Leather Dyke Picnic, a chocolate chip-sprinkled cheesecake cupcake; and two relatively new organizations, Women, Trans, Non-Binary (WTNB) Leather Kink Social, represented by a lemon hibiscus cupcake with lemon butter cream frosting, and Second City Boot Blacks, with a vegan orange chocolate cupcake with raspberry filling topped with butter cream frosting.
Apart from the Master Baker title, prizes were given out for Fan Favorite, Judges Choice, and Raise the Dough for fundraising. The fundraising element of the evening involved audience members buying five-dollar scorecards and sampling each entry for preference as the judges did the same.
One of the most popular aspects of the Cupcake Wars is a segment where bakers auction off full-sized cupcakes and can throw in off-site prizes and services for the highest bidder. In something of a saucy surprise, baker Joey Metler of Mr. Chicago Leather fueled bidding for his cupcake by stripping off an article of clothing for each escalating bid and the opportunity to “do anything you want.”
Needless to say bidding for his prizes was the most aggressive and tied with Justin and Hugh from The Chicago Hellfire Club’s top bid of $200.
That was hardly the biggest surprise of the night though, as bakers Justin and Hugh’s “salty surprise” swept the top prizes. For the ‘Judges Choice’ Lola Sunshine of WTNB took second place, with Emily of Illinois Gay Rodeo Association taking third.
Fan Favorite second place winner was WTNB again, with Corso and Finch of Second City Boot Blacks taking third. Mr. Chicago Leather took second place in Raise the Dough, while third place went to Corso and Finch of Second City Boot Blacks.
