• Andrew McGuinness

Why The Philadelphia Flyers Did Not Win the 2019 Stanley Cup... And All the Ones Before It

The 2019 Stanley Cup Finals are on the tip of the hockey world's tongue. At some point in the next three weeks, heroes will emerge, memories will be forged, and one team and it's fanbase will witness the ultimate joy that is the whole reason we play and watch this glorious sport anyway.

Unfortunately, none of those heroes will come from the Philadelphia Flyers. Two months ago Thursday, the Flyers played their final meaningful game of the 2018-19 season. Needing a miracle to qualify for the playoffs, the Flyers were soundly beaten 5-2 by Carolina, officially killing Philadelphia's Cup hopes.

This year marked the fourth time in the last seven years the Flyers have missed the playoffs. They have not won, let alone led, a single series in that time span. Philadelphia has won just seven playoff games since 2012, being outscored 61-37 in ninteen games. Whether it's been the stars going silent, the depth falling dead, or a gamping casam in goal, the Flyers have not been able to get the job done.

But why? While it's been easy to spot the Flyers fatal flaws on the ice, the reasons why they occurred can be found high above the Wells Fargo Center's ice.

Earlier this year, I wrote about the Jeff Carter and Mike Richards trade trees. These deals, which occurred within hours of each other, completely changed the Flyers identity. But that wasn't a bad thing. Though successful on paper, the 2011 squad that was swept in Round 2 by Boston clearly had internal issues. These two deals netted four young forwards that played big roles beginning the very next year and a few more picks.

These two moves did not lead to the downfall of the Philadelphia Flyers - far from it, actually. So what did?

Nearly every move after. For the next three years.

Throughout their history, the Flyers were one of the more aggressive teams in the NHL when it came to both free agency and big trades. Paul Holmgren, the team's general manager at the time, fit this bill to a tee. That was fine when the salary cap didn't exist - with it, it's a major problem. The scary thing is that things could've been even worse - had the Shea Weber offersheet not been matched, the Flyers could've been stuck with a good defender on an albatross contract (though Marc Bergevin may still have bailed them out).

There's no easy way to do this, so we'll keep it simple. Here is every single notable move the Philadelphia Flyers made after the Carter and Richards deals through May 7th, 2014 - the day Holmgren was fired via promotion to president, swaped for the recently-replaced Ron Hextall.

Transaction 1 - June 23, 2011

PHI Acquires

Rights to UFA G Ilya Bryzgalov - Signed to 9 Year, $41,880,000 Contract ($4,653,333 AAV)

PHX Acquires

RW Matt Clackson

2011 PIT 3rd (#84 - D Harrison Ruopp)

2012 PHI 3rd (#81 - C Oskar Sundqvist)

The 2011 Stanley Cup Playoffs exposed the Flyers confusing goaltending situation. Michael Leighton, Brian Boucher, and Sergei Bobrovsky all started games in the playoffs, and all posted save percentages below .905. The Flyers, desperate for stability in the crease, made a rash decision. Rather than trust Bobrovsky, fresh off an outstanding rookie season (.915 save percentage in 52 starts), Homer went all-out, trading for pending UFA Bryzgalov's rights and then signing him to a massive 9-year pact, trading two picks (one that turned into a legit NHLer in Sundqvist) in the process.

It was a disaster on multiple fronts. Bryzgalov was awful in Philadelphia, posting a .905 save percentage (.887 in the playoffs) in two years as a Flyer. To this day, Bryz is still more known for his half-hilarious, half-moronic interviews with the media and HBO. This deal led directly to another disastorous move later on this list, too. Though the Flyers were able to escape the cap complications by using a compliance buyout on Bryzgalov two years into the contract, by then it had already made its devastating mark on the Flyers crease, and team as a whole.

Transaction 2 - July 1, 2011

RW Jaromir Jagr Signs 1 Year, $3.3 Million Contract

While most of the moves in this list will be negative (hence the title), there were a few moves that actually paid off. Jagr was one nut that the Flyers blind squirrel was able to find. Returning to the NHL for the first time since the 07-08 season, Jagr chose to come to Philadelphia on the perfect low-risk, high-reward any GM should look to make.

Holmgren pounced on the chance, and Jagr wound up fitting in seamlessly in Philadelphia, creating a juggernaut of a top line with Scott Hartnell and Claude Giroux. Jagr's 54 points were third on the Flyers that year (behind only Hartnell and Giroux). If anything, the only thing you can criticize is that Holmgren let Jagr leave on a one year, $4.5 million deal with Dallas the next summer. This was one of his most shrewd moves as GM.

Transaction 3 - July 8, 2011

LW Max Talbot Signs 5 Year, $9 Million Contract ($1.8 Million AAV)

This, on the other hand, was not. This may come as a surprise to some Flyers fans, considering Talbot was a fan favorite in Philadelphia. But giving a 5-year deal to someone who had never scored more than 26 points is a major red flag. Talbot did have a career-high 34 points his first year in Philly. But it proved to be a mirage, as Talbot's production dropped shortly after and he was dumped to Colorado about halfway into the deal. Not a detrimental deal, but certainly not a good one.

Transaction 4 - February 16, 2012

PHI Acquires

D Nicklas Grossmann - Signed to 4 Year, $14 Million Extension ($3.5 Million AAV)

DAL Acquires

2012 LA 2nd (#61 - C Devin Shore)

2013 MIN 3rd (#77 - LW Jake Guentzel)

Even if you ignore the names of the two players taken with the picks the Flyers gave up, this wasn't a very good trade. Looking to upgrade the Flyers blueline in response to the Chris Pronger injury, Holmgren parted with two picks in exchange for physical defenseman Nicklas Grossmann. Granted, physical defensive defenseman still had a place in the league back then. But it shouldn't cost a 2nd and 3rd to acquire someone with 5 goals in 5 seasons, even if their main job wasn't to score.

The fact that both picks turned into NHL contributers makes it even more painful. Shore is a decent middle-six, defensively sound center, but it's the latter name that makes this move so painful. The 3rd was flipped to the Penguins, allowing them to select the same Guentzel that dominated the 2017 Finals and scored four goals in Game 6 to eliminate the Flyers in 2018. By not making this deal, Holmgren could've saved the Flyers an albatross contract, kept the money to bring back Matt Carle, and prevented a playoff elimination six years down the road.

*Wheeps into Gritty pillow*

Transaction 5 - June 22, 2012

PHI Acquires

2012 OTT 2nd (#45 - G Anthony Stolarz)

2014 VAN 4th (#117 - LW Taylor Leier)

2013 ARI 4th (#103 - RW Justin Auger)

CBJ Acquires

G Sergei Bobrovsky

Ever since Ron Hextall, the Flyers had been looking for a stable option between the pipes. Names such as Robert Esche, Martin Biron, and Michael Leighton were unable to hold down the crease long-term. Unbeknownst to Holmgren, the Flyers already had their goalie of the future in Bobrovsky. Despite a rough playoff debut in 2011, the Flyers would've been much better riding Bobrovsky long-term.

Instead, the splash move of Bryzgalov pushed him out of the picture. Bob struggled in a lesser role in 2012, and in the offseason was sent to Columbus for a few mid-round picks. Bobrovsky was absolutely dominate his first year in Columbus, winning his first of two Vezinas in the 2012-13 campaign. Bryz posted a .900 save percentage that year, and was bought out in the summer. Had the Flyers kept Bobrovsky, he could've given Philadelphia an elite netminder for a half-decade.

The scary part? He still wasn't done.

Transaction 6 - June 22, 2012

C Scott Laughton Selected #20

Laughton saved himself from potentially falling to complete bust status by establishing a niche on the Flyers bottom six the last two seasons. That being said, that type of player does not warrant a first round selection. Defenseman Mike Matheson and Brady Skjei, both picked later in the first round, would have been much better choices (though taking Shayne Gostisbehere in the 3rd round helped save this draft).

Transaction 7 - June 23, 2012

PHI Acquires

D Luke Schenn

TOR Acquires

LW James van Riemsdyk

It's not a stretch to say that in just two days,the Flyers back set themselves back years. After seeing the Flyers fail to contain the New Jersey Devils in the second round of the playoffs, falling in five games, Homer decided the defense needed to change.

That thinking wasn't a problem. What was is that, like Grossmann, Schenn was a burly, physical defenseman, the same style that was fading fast from the NHL. Schenn never lived up to the hype of being a top-5 pick; van Riemsdyk, on the other hand, did, developing into a 30-goal scorer with the Maple Leafs. While it's nice that JVR came home last summer, he should've never had to leave, at least like that, in the first place.

Transaction 8 - April 3, 2013

PHI Acquires

G Steve Mason

CBJ Acquires

G Michael Leighton

2015 PHI 3rd (#68 - RW Martins Dzierkals)

Needless to say, the second move involving a goaltender between the Flyers and Jackets went much better for the Orange and Black. Mason, a former Calder winner that was in danger of falling off, desperately needed a change of scenery. With Bobrovsky set as the team's long-term starter, 'Lumbus could afford to ship out Mason. Holmgren took advantage, sending a past-prime Leighton and 3rd to acquire Stone Cold Stevie Mae.

While he was no Bob in his four-year tenure, Mason was spectacular his first three years with the Flyers, particularly in 2014-15, when his .928 save percentage was 3rd in the NHL (minimum 25 games played). He was great in the 2014 playoffs despite missing the first three games to injury, but struggled in 2016 after being overused down the stretch. Mason struggled in the 2016-17 season, and was allowed to walk to Winnipeg.

Transaction 9 - June 12, 2013

PHI Acquires

Rights to UFA D Mark Streit - Signed to 4 Year, $21 Million Contract ($5.25 Million AAV)

NYI Acquires

RW Shane Harper

2014 PHI 4th (#108 - D Devon Toews)

Another flawed move for an aging pending UFA's rights, followed by signing him to a questionable four-year contract. Yay.

At least he wasn't a defensive defenseman.

To be fair, the Streit contract, while risky at the time, actually paid off. Streit was a solid point-producing defenseman for three and a half years before being shipped out for a decent haul at the 2017 deadline. Unfortunately, the fourth round pick here wound up becoming Devon Toews, a budding defenseman who spent time on the Isles top power-play unit. It's hard to say from hindsight, but how much of an advantage did the two-week head start really give the Flyers?

Transaction 10 - June 30, 2013

D Samuel Morin Selected #11

Morin fit the tall, imposing, poor puck moving model that Holmgren believed a defenseman should be, but that the NHL was quickly rendering obsolete. Morin is still just 23, so his legacy is still be shaped. But he has played just eight NHL games and projects to be no more than a 3rd pairing defenseman. Max Domi, Alexander Wennberg, Ryan Pulock, and Nikita Zadorov were the next four picks - any of them would have been a much better fit.

Transaction 11 - July 2, 2013

C Vincent Lecavalier Signs 5 Year, $22.5 Million Contract ($4.5 Million AAV)

If you look at a list of notable Flyers alumni, you can find some of the all-time NHL greats. However, some deserve an asterisk next to their name, as they were acquired near the end of their legendary careers when they were nowhere near as good as people remember them. Vinny Lecavalier deserves this asterisk. This was not a problem before the salary cap, but in 2013, Lecavalier's massive deal was a gut-punch to the Flyers already terrible cap situation.

To say Lecavalier was a dud in Philadelphia would be an understatement. By year one of the deal, he was already relegated to a bottom-six role. Dave Hakstol flat-out refused to play him in the 2015-16 season because of how bad he was. Though Ron Hextall was able to miraculously pawn him (and Luke Schenn) off to Los Angeles, that doesn't excuse the bad decision and awful fit that signing Lecavalier was.

Transaction 12 - March 4, 2014

PHI Acquires

D Andrew MacDonald - Signed to 6 Year, $30 Million Extension ($5 Million AAV)

NYI Acquires

C Matt Mangene

2014 PHI 3rd (#78 - G Ilya Sorokin)

2015 PHI 2nd (#37 - D Brandon Carlo)

There are so many terrible layers on this deal. First, MacDonald himself. Heralded as a legitimate top-four blueliner when he first arrive, MacDonald's flaws were laid out for all to see during his first full campaign (2014-15). It went so terribly that he spent most of the 2015-16 season in the AHL. But then Dave Hakstol fell in love with him and AMac spent two and a half years in the Flyers top four despite atrocious puck movement and moronic defensive zone coverage.

Acquiring MacDonald in the first place wasn't a great move. But then came the extension. Oh, the extension. 6 years. 30 million. The term and the value have been mocked by all sects of the Flyers and hockey fanbase. It was part of the reason why MacDonald was relegated to the minors in the 2015-16 campaign and has amplified his critics cries for him to never see the Wells Fargo Center ice again.

To pour a little more salt on the wound, take a look at what those two draft picks became. Carlo is a developing top four defenseman on the Eastern Conference Champion Bruins, and Sorokin is arguably the best goalie prospect in the NHL (until Spencer Knight is drafted).

So, to recap:


Bryzgalov Megadeal

Giving Away Bob and JVR in a 2 Day Span

Lecavalier Albatross

MacDonald Trade and Extension

Trading Away Picks Used to Take Guentzel, Carlo, Sorokin, and Devon Toews


Stole Mason from Columbus

Jagr Signing Was an Excellent Fit

That's a pretty lopsided list. It basically forms a demonic type of hat trick - three unmoveable contracts, three terrible trades, and three elite young talents wasted (Toews is a peg below). Between the salary cap and the useless veterans and the lack of young talent, the Flyers have became one of the most mediocre and frusturating teams in the NHL. And they haven't broken out of that spell since.

You can't blame those three years for Brian Elliott being hurt, or the Flyers PK being terrible, or the regression of Provorov and Gostisbehere, or any other reason the Flyers struggled this season. But all of these nightmare moves have cost the Flyers, not just this year, but in all the ones between them. Imagine if the Flyers have had Bobrovsky in net or van Riemsdyk upfront or Carlo on the backend in the last few years.

They still might not have won the Cup. But they would have been a lot closer. And they probably still would be today.