Teams in the NHL have been trading for over a century at this point. So the title of ‘worst’ in the history of the competition is hard to come by. But the double whammy of the Philadelphia Flyers’ Sergei Bobrovsky trade could 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 disaster?
Who is Bobrovsky? Why did the Flyers trade him?
Long ago, Bobrovsky was an undrafted free agent who the Flyers took a gamble on. He was stellar in the Kontinental Hockey League (KHL) between the ages of 20 and 21, with a cumulative save percentage of .923 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. Relying on third-string journeyman Michael Leighton, they needed an upgrade in the final two rounds of the postseason. Bobrovsky played 54 games for the dominant 2010–11 Flyers (third place in the NHL standings) and certainly lived up to that expectation.
As a rookie, Bobrovsky posted a .915 save percentage, a 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 that saw him lose his starting job in Round 1 led the team to rethink things a bit.
In a Cup era, the Flyers felt like they didn’t have time to deal with the ups and downs of a young goaltender. So they offered a contract to the best man on the market: Ilya Bryzgalov. By signing a nine-year deal worth a total of $51 million, the writing was on the wall for Bobrovsky. I don’t want to be a backup for nine years, he quickly demanded a trade.
The Bobrovsky trade: harmful and insulting
This is where things get bad for the Flyers. In 2011-12, Bryzgalov and Bobrovsky shared the crease, but 57 starts went to the $51 million man. He had a .909 save percentage, a 2.48 goals-against average and a 33–16–7 record. The postseason was quite discouraging, with an .887 save percentage through eleven games, but Philadelphia committed to the highly paid veteran. Bobrovsky was dealt to Columbus in the summer.
Related: Flyers’ 2011 offseason brought years of bad luck
From that point on, the Flyers’ franchise hasn’t been the same, and neither have the goaltenders. In the 2012–13 campaign, Bobrovsky won the Vezina Trophy as the league’s top netminder, with a .932 save percentage over 38 games in the shortened season. Bryzgalov, meanwhile, played 40 games and had a .900 save percentage, which led 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 go all the way to the present. Bobrovsky has two Vezina trophies and two Stanley Cups to his name. He may be 37 years old, but he is far from ‘washed’. Those championship victories in fact came at ages 35 and 36, and he was the first goaltender to record a win in 2025-2026.
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 one series win to their name. Philadelphia has not hosted a postseason second-round game since the move.
Even more than thirteen years later, the Flyers are feeling the double whammy of it all. First, Bobrovsky is chasing his third straight championship ring with the Florida Panthers. Second, Bryzgalov is still receiving checks from Philadelphia not to play for their team – the buyout penalty runs through 2027. After all, the Flyers posted the NHL’s worst team save percentage of 21 last season.st century: .879, according to QuantHockey.
The Bobrovsky trade is the worst in league history as it marked the demise of a once great franchise. Young stars Matvei Michkov and Porter Martone may be able to help the team return to its glory days, but for now this decision continues to haunt the Flyers.
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