If you had a nickel for every time the Flyers, goaltending, and playoff failure were tied together, well…you would have a lot of nickels. Despite trying their best at times, or having the best of intentions on the day the Flyers reached out to sign a goaltender in unrestricted free agency, sometimes things went pear-shaped quite quickly. Looking back, there have been some signings that belong on the Mount Rushmore of lunacy. But because there’s only so much bandwidth, we’ve decided to narrow it down to just three signings.

Here then are the three worst free agent goalie signings the Flyers have made, in no particular order (although after reading you’ll put them in order yourselves).

1) Jeff Hackett — July 1, 2003

With Roman Cechmanek not capable of doing the job, the Flyers once again needed to find the goaltender who would get them deep into the playoffs and eventually a chance for their third Stanley Cup. They put all their cards on the table, all their chips in the pot, and decided one goalie was capable of doing just that. That goal was, er, Jeff Hackett.

Hackett spent the previous season between Montreal and Boston. In 18 appearances with the Habs, Hackett was a game under .500 with a 2.54 goals-against average and a .926 save percentage. Montreal then traded Hackett to San Jose on Jan. 23, 2003 for Niklas Sundstrom and a third-round pick in 2004. San Jose then flipped Hackett off to Boston (along with Jeff Jillson) for Kyle McLaren and a 2004 fourth-round pick. In his regular season stint with the Bruins Hackett had a 3.21 goals-against average and a .894 save percentage. The playoffs were a different story for the goalie, despite playing only three games. The netminder had a solid .934 save percentage, winning one of three games for the Bruins who lost to the Devils in five games in the opening round.

Maybe it was that short playoff spurt that clouded the Flyers judgment. But early in July 2003, Philadelphia pulled the trigger, signing Hackett to a two-year contract. “Our scouting staff, our coaching staff, our whole organization feels that Jeff Hackett will give us the solid and steady goaltending that we will need to take a run at the Stanley Cup,” Flyers general manager Bob Clarke said on signing Hackett at the time.

Hackett started the season with two consecutive shutouts, so clearly the early results demonstrated Hackett was the real deal. Things were rolling along, with Hackett losing only two games in his first two months of play. In November Hackett was 5-0-1 and that ridiculously hot streak continued through the first five games in December where he went 3-0-2. However, beginning with a 2-0 loss to New Jersey on Dec. 13, 2003, Hackett lost six consecutive games to close out 2003. An early January victory temporarily righted the ship. But it was short-lived as Hackett lost the next three games, including a 6-2 loss to on Jan. 13, 2004.

Sadly for Hackett (and the Flyers) it wasn’t just poor positioning and terrible rebound control that was affecting him. It was a serious medical condition: vertigo (a sense that your spinning or moving causing dizziness). Hackett was kept off the ice for about a month, then decided to go to the American Hockey League to play a game for the Phantoms (then playing in Philadelphia). After that Feb. 6 game, Hackett simply couldn’t hack it anymore. He announced his retirement on Feb. 9. He finished his season going 10-10-6, posting a .905 save percentage and a 2.39 goals-against average.

Clearly nobody could foresee the problem Hackett encountered that ended his career. But the Flyers ran into a bit of good fortune thanks to the 2004-05 lockout, effectively giving them a year to try to figure out how to move forward after Hackett and the resulting disaster. By the time the 2005-06 season rolled around, few were thinking of Hackett, instead focusing on what Robert Esche and Antero Niittymaki would do. It started off so well, but it ended miserably for all concerned.

2) Ray Emery — June 10, 2009

After former Senators goaltender Ray Emery wore out his welcome in Canada’s capital, he ended up playing in Russia in the KHL. But due to KHL rules giving Russian-born goaltenders a chance to play, Emery was only able to play approximately two-thirds of games that season. That’s not a lot considering there were fewer than 60 regular season games that year (56 to be exact). But he managed to start fresh, particularly after how the Senators situation steadily unraveled following getting dinged for speeding in Ottawa and reportedly one instance of road rage.

Flyers general manager Paul Holmgren, who had battled his own personal demons, saw Emery as a great chance for the Flyers to improve while at the same time helping a once great goaltender get back in the spotlight. “I spent a great deal of time talking with Ray,” Holmgren said at the time of the signing. “The thing that kept coming back is he’s recognized there was a period in his life when he made some mistakes.”

“I learned maybe more from those bad experiences than the good times we had there,” Emery said on signing with Philadelphia. “I realize I had a great thing going and lost a lot of people that I enjoyed hanging out with. I want to get back to having those good relationships. I think that’s the reason I’m going to change.”

Emery, much like Hackett, started the 2009-10 season strong and steady. He was 16-11-1 with a .905 save percentage and a respectable 2.64 goals-against average. He was providing great numbers and it looked to be a promising and pleasing outcome on the one-year deal. But things were starting to come to the surface. A problem with his abdomen was discovered in November, but Emery reportedly tried cortisone shots and rehabilitation to help the injury and avoid going under the knife. On Dec. 8 it was announced Emery would go under the knife to fix the torn abdominal muscle.

“You know how hard he practices,” Holmgren said when announcing that surgery was needed. “He’s been trying to fight through this, but couldn’t practice the way he normally does, and his game suffered. He’s a down young man, and feels he let his team down. It has gotten progressively worse. The tests and the MRI we’ve done showed a tear in his abdominal wall.”

That was just the tip of the iceberg. Doctors discovered far more serious problems Emery was facing: Avascular necrosis in his right hip. In layman’s terms, Emery’s hip was dying and rotting away. Forget hockey. Doctors just wanted Emery to be able to walk again. However Emery had bigger aspirations, and underwent an arduous, invasive procedure: bone from his fibula was taken out and placed where the dying portion of the hip bone once was.

Needless to say, Emery’s season with the Flyers ended with that news. The Flyers wished Emery the best but realized it was a small chance Emery would ever play again in the NHL. Even more bittersweet was the fact the Flyers made an improbable run to the Cup finals later that season, a playoff run a healthy Emery might have made a difference in. But it was not to be. The first go around was messy for both sides. But it wasn’t the end of the story.

In March 2011 Emery returned, playing for Anaheim. The feel good story continued with six consecutive wins. He then signed a contract with Chicago, earning two consecutive one-year deals and putting up good numbers. Finally, a little over four years from first signing with Philadelphia, Emery signed a one-year deal with the Flyers. And then another the following year for $1 million. The two-year stint was highlighted by a glorious old-school brawl the Flyers and Capitals got involved in back in November 2013. Emery beat the supreme feces out of Capitals goaltender Brayden Holtby on that night.

Emery played his last NHL games with the Flyers in 2014-15. Tragically, Emery died in a drowning accident in Hamilton on July 15, 2018. He was just 35 years young.

3) Ilya Bryzgalov — June 23, 2011

The capo du tutti capi of all-time bad Flyer free agent signings, goaltender or otherwise. The day that will live long in Flyers history began with the trading of Jeff Carter and Mike Richards to Columbus and Los Angeles, respectively. The trades of two forwards — both of whom had essentially locked themselves into ending their career as Flyers with lengthy contracts — made Philadelphia a little bit younger and cleared cap space. That cap space was used to sign Bryzgalov, a player they needed to lock in before the free agency deadline started as they acquired his rights in a June 7 deal. Hours after the two massive trades were made, the Flyers announced that Bryzgalov was a Flyer. For nine years. And $51,000,00! The Flyers finally found their answer in goal. No really, this was the guy!

Bryzgalov’s tenure with the Flyers started with three straight wins including a shutout. Then he came back down to earth the following five games, all of them losses with save percentages under .900 (including stopping 6 of 10 shots against Winnipeg in a nutty 9-8 loss). Suddenly, there were a few more concerns with Bryzgalov. Meanwhile off the ice, the goaltender’s approach with the media was lighthearted and amusing, making some feel he wasn’t serious about his game or the outcomes.

Bryzgalov was streaky, which is okay for a goal scorer like Owen Tippett, but pure hell on earth for teams relying on consistently good goaltending. A seven-game winning streak for the keeper was followed by a four-game losing streak with Bryzgalov in goal. Up and down. Another seven-game streak in March consisted of four being shutouts, with Bryzgalov in the zone. In 57 games, he had a .909 save percentage and 2.48 goals-against average. Not stellar, but again with highs and lows.

The 2012 first-round matchup against the Penguins has been exhaustively recounted. Needless to say Bryzgalov looked a tad more competent and Marc-Andre Fleury did. But that’s not saying a lot. In round two he faced the Devils, having moments of great saves but other moments leaving people scratching their heads. The first year would be a chance for Bryzgalov to work out the kinks in a new city with his new team for the long run. The second year would be better…right?

The second Bryzgalov season was worse than the first one. Despite a lockout shortening the season, Bryzgalov’s goals-against average ballooned to 2.79 while his save percentage dropped to .900. He only had one shutout, a 7-0 win over the Islanders. A ten-game stretch in March saw him with just two wins against eight losses, most of those seeing him letting in goals that your average NHL goaltender wouldn’t be giving up, let alone a supposed cornerstone of the franchise for the rest of the ’10s. The Flyers missed the playoffs and Bryzgalov was done.

On June 25, 2013, two years and two days after welcoming him with open arms (and an open chequebook), Bryzgalov was bought out of his remaining seven years, severing his ties with Philadelphia by using one of the two compliance buyouts each team was allotted after the lockout. “Obviously it’s a costly mistake that we made,” general manager Paul Holmgren said regarding the situation. “You know Ilya, it’s hard to fault him. I still believe he played pretty good, but in a salary-cap world, you need to make decisions from time to time that put you in a better light moving forward and this is one of those.”

The move eventually changed in some respects how the Flyers went about addressing their goaltending issues. Large, long-term contracts to goaltenders the Flyers didn’t draft or develop were put on the backburner a bit. Instead the team focused on drafting goaltenders and building from within. Those UFAs who were signed were given far fewer years and often far less money to perform. And none of them (until perhaps Dan Vladar this coming season) were expected to be anything more than a reliable backup.

If you want to remember Bryzgalov’s contract, it is still on the books on some cap-centric sites. Although he is $0 on the official salary cap, Bryzgalov is being paid by the Flyers just under a reported $2 million a season. That will conclude at the end of the 2026-27 season. And our long nightmare will officially be over.