One of the worst trades in St. Louis Blues history was the deal that sent Chris Pronger to the Edmonton Oilers in August 2005. Pronger, a dominant defenseman and team captain, was a crucial cornerstone of the Blues franchise and a fan favorite. The trade was made after Pronger requested to be moved following contract disputes. In exchange for Pronger, the Blues received a package that included defensemen Eric Brewer, Doug Lynch, and forward Jeff Woywitka. While Brewer had a respectable tenure with the Blues, the overall impact of the trade was heavily one-sided in favor of the Oilers. Pronger's departure left a massive void on the blue line and significantly weakened the team's defensive prowess. Compounding the issue, Pronger went on to have tremendous success with the Oilers, leading them to the Stanley Cup Finals in 2006 and winning the Hart Trophy as league MVP. Meanwhile, the Blues struggled to find a suitable replacement for their former star, making this trade a painful reminder of a missed opportunity and a major setback for the franchise.

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