Windy City Gridiron Publishes Three All-Time Chicago Bears Fantasy-Draft Teams

Using a 25-player, position-specific draft that 'transports' each player's skills to the modern era, the series will conclude with a reader vote once all eight teams are posted.

Overview

Windy City Gridiron has published three of eight planned All-Time Historical Chicago Bears rosters so far, with entries released across June 25–27 that apply the series' shared draft rules.
Each roster follows a fixed 25-player format with 11 offensive slots, 11 defensive slots, and three special-teams slots and treats each player's historical ability as if adapted to today’s game.
Authors highlighted different roster philosophies in the published pieces, including era-focused selections (Sid Luckman, Bronko Nagurski), trench-and-identity choices (Bill George), and a special-teams emphasis that features Devin Hester as the primary returner.
The site has posted a tournament bracket pairing the eight planned teams and says it will run a reader-voted tournament to determine the best draft once all teams are revealed.
Beyond the matchups, the series aims to teach readers about Bears history by centering Hall of Famers and franchise standouts and it ties into broader fan engagement including a referenced charity partnership linked to the Gridiron Greats project.