The Sergei Bobrovsky trade by the Philadelphia Flyers on June 22, 2012, to the Columbus Blue Jackets is increasingly viewed as one of the most regrettable transactions in NHL history. Hindsight, amplified by Bobrovsky's subsequent success, casts a harsh light on the Flyers' decision to part ways with the promising young goaltender.

At the time, the Flyers were in a Stanley Cup window, and despite reaching the 2010 Stanley Cup Final, they identified goaltending as a weakness. Bobrovsky, an undrafted free agent, had shown promise in the Kontinental Hockey League (KHL) and impressed during his rookie season with the Flyers, posting a .915 save percentage and a 2.59 goals-against average. However, a shaky playoff performance led the Flyers to question his ability to be their long-term solution in net.

Driven by a perceived need for immediate stability, the Flyers traded Bobrovsky for a package of draft picks: a 2012 second-round pick (Anthony Stolarz), a 2012 fourth-round pick (Taylor Leier), and a 2013 fourth-round pick (Justin Auger). None of these players achieved substantial success with the Flyers or elsewhere in the NHL. Stolarz ironically became Bobrovsky's backup on the Florida Panthers.

Meanwhile, Bobrovsky blossomed into one of the league's premier goaltenders after leaving Philadelphia. He won two Vezina Trophies as the NHL's best goalie and led the Florida Panthers to back-to-back Stanley Cup Finals in 2023 and 2024, winning the Stanley Cup in 2024. His consistent excellence and playoff heroics stand in stark contrast to the Flyers' continued struggles to find a franchise goaltender.

The Flyers' search for a reliable goalie has been a recurring source of stress and disappointment for fans. The team's save percentage this past season was the worst in the NHL. This ongoing goaltending instability, juxtaposed with Bobrovsky's accomplishments, has cemented the trade's legacy as a major misstep.

While some argue that it was impossible to predict Bobrovsky's future stardom, the Flyers' impatience and misjudgment are undeniable. The trade not only deprived the Flyers of a potential franchise cornerstone but also yielded virtually no return. As Bobrovsky continues to excel, the Flyers are left to grapple with the consequences of a decision that continues to haunt the franchise.