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Teams in the NHL have been trading for over a century at this point. So, the title of the “worst” in league history is hard to obtain. But the double whammy of the Philadelphia Flyers‘ Sergei Bobrovsky trade might just take the cake.
On June 22, 2012, the Flyers dealt Bobrovsky to the Columbus Blue Jackets for a 2012 second-round pick (Anthony Stolarz), a 2012 fourth-round pick (Taylor Leier), and a 2013 fourth-round pick (traded). What makes this deal such a calamity?
Who Is Bobrovsky? Why Did the Flyers Trade Him?
Way back when, Bobrovsky was an undrafted free agent whom the Flyers took a chance on. He was terrific in the Kontinental Hockey League (KHL) between the ages of 20 and 21, posting a cumulative .923 save percentage and 2.62 goals-against despite a 15–38–5 record.
While the Flyers reached the 2010 Stanley Cup Final, their biggest weakness was goaltending. Depending on Michael Leighton, a third-string journeyman, in the last two rounds of the postseason, they needed an upgrade. Playing 54 contests for the dominant 2010–11 Flyers (third place in the NHL standings), Bobrovsky certainly lived up to that expectation.
As a rookie, Bobrovsky put up a .915 save percentage, 2.59 goals-against average, and a 28–13–8 record in Philadelphia. Those are fantastic numbers for someone his age—indicative of a future star. However, a disappointing playoff run, which saw him lose his starting job in Round 1, led to the team rethinking things a bit.
In a Cup window, the Flyers felt they didn’t have time to deal with the ups and downs of a young goalie. So, they offered a contract to the best guy on the market: Ilya Bryzgalov. Signing a nine-year deal worth $51 million in total value, the writing was on the wall for Bobrovsky. Not wanting to be a backup for nine years, he quickly demanded a trade.
The Bobrovsky Trade: Detrimental and Insulting
Here’s where things get bad for the Flyers. In 2011–12, Bryzgalov and Bobrovsky shared the crease, but 57 starts belonged to the $51 million man. He had a .909 save percentage, 2.48 goals-against average, and a 33–16–7 record. The postseason was pretty discouraging, with a .887 save percentage across 11 games, but Philadelphia was committed to the high-paid veteran. Bobrovsky was dealt to Columbus in the summer.
Related: Flyers’ 2011 Offseason Has Caused Years of Misfortune
From that point forward, the Flyers’ franchise hasn’t been the same—and neither have the goalies. The 2012–13 campaign saw Bobrovsky win the Vezina Trophy as the league’s best netminder, posting a .932 save percentage across 38 games in the shortened season. Bryzgalov, meanwhile, played 40 games and had a .900 save percentage, leading to Philadelphia missing the playoffs for the first time since 2006–07. The remaining seven years of his contract were bought out on June 25, 2013.
Let’s move all the way up to the present. Bobrovsky has two Vezina Trophies and two Stanley Cups to his name. He may be 37 years of age, but he’s far from “washed.” Those championship wins came at ages 35 and 36, in fact, and he was the first goaltender to record a victory in 2025–26.
Then, you have the Flyers. Before the Bobrovsky trade, they were one of the league’s model franchises: eight Stanley Cup Final appearances and only eight playoff misses in 44 seasons. But since moving on from the future Hall of Famer, they have missed the playoffs nine times in 13 seasons and have just a single series victory to their name. Philadelphia has not hosted a second-round postseason game since the move.
Even over 13 years later, the Flyers are feeling the double whammy of it all. First, Bobrovsky is chasing his third consecutive championship ring with the Florida Panthers. Second, Bryzgalov is still receiving checks from Philadelphia to not play for their team—the buyout penalty runs through 2027. Finally, last season, the Flyers posted the NHL’s worst team save percentage of the 21st century: .879, according to QuantHockey.
The Bobrovsky trade is the worst in league history because it has marked the downfall of a once-great franchise. Young stars Matvei Michkov and Porter Martone may help the team return to its glory days, but for now, this decision continues to haunt the Flyers.