It’s been quite a while since the Philadelphia Flyers were central figures at the NHL trade deadline.
In their heyday, though, the Flyers were consistently one of the most aggressive buyers, constantly looking to bulk up their roster for an inevitable playoff push. But over the past decade? The closest they’ve come to taking center stage was last season when they shipped longtime captain Claude Giroux to Florida, the only team that he would waive his no-trade clause to join.
Franchise-changing? Sure. But there was no bidding war, no deluge of offers. The Flyers decided they had to trade Giroux given their dismal season, and they did it. There aren’t many “what ifs” in its aftermath.
But that doesn’t mean the Flyers are completely lacking for trade deadline “what ifs” over the past 10 years.
So with the 2023 deadline less than a week away, it’s time to play the alternate history game. What if four key decisions made by three separate Flyers general managers at the deadline since 2013 went the other way? What if some trades didn’t happen? What if other potential trades did happen? And what might have been the long-term impact of all of them?
Let’s hop in our time machine and take a look back on deadlines past.
The 2022 trade deadline for the Flyers will long be remembered for the trade that general manager Chuck Fletcher did make in dealing Giroux to the Panthers.
But just as impactful over the long-term was one he didn’t: selling the soon-to-be UFA Rasmus Ristolainen.
When the Flyers traded for Ristolainen in the summer of 2021, they did so knowing he was a “rental,” with just one year remaining on his contract before he could leave via free agency. But Fletcher made it clear that he had designs on trying to keep the defenseman beyond 2021-22. However, he didn’t expect 2021-22 to go the way it did: a full team collapse, the firing of Alain Vigneault and ultimately the league’s fourth-worst record.
An expected buyer had become a clear-cut seller — and Ristolainen was a logical candidate to be sold.
And for a while, it appeared that Ristolainen would indeed be moved. Throughout February, he was popping up in scattered trade rumors, as contending clubs looked to beef up their blue line corps with physical defensemen supposedly “built for the playoffs.” Instead, 11 days before the deadline, the Flyers announced that rather than trade Ristolainen, they had extended him, agreeing to a five-year, $25.5 million contract that would kick in at the start of 2022-23.
Ristolainen was officially off the trade block.
But there is a scenario where Ristolainen’s ask proved too ambitious, or the Flyers simply determined that the better course would be to try to recoup some of the assets they spent bringing him in. What if that had been Fletcher’s final call?
For starters, they probably would have gotten a nice haul. Ben Chiarot — a defenseman with similar appeal for his physicality but three years older and not right-handed — returned a first and a third-round pick (plus a minor prospect) just five days after Ristolainen’s extension was finalized. It’s certainly possible — if not likely — that Ristolainen gets a similar return. At the very least, it’s difficult to imagine he would have brought back less than a second-rounder.
They also would have gotten something else: cap space.
Absent Ristolainen in 2022-23, they would have had an additional $5.1 million in cap flexibility entering the 2022 offseason. Which raises an interesting question: had the Flyers traded Ristolainen, could they have gone Johnny Gaudreau hunting without having to pay to clear James van Riemsdyk’s onerous $7 million cap hit?
The short answer is maybe.
Assuming the rest of Fletcher’s offseason moves still occurred — adding Tony DeAngelo, signing Nicolas Deslauriers, buying out Oskar Lindblom, bringing back Justin Braun, and re-signing all of the pending restricted free agents — the Flyers would have had about $4.64 million in cap space left for Gaudreau, who ultimately signed for $9.75 million per year with Columbus. So that’s not enough, even with a hometown discount.
However, the acquisition of DeAngelo certainly hinted that by July, the Flyers had largely given up on the possibility of a Ryan Ellis return — otherwise, why spend three draft picks and $5 million worth of cap space on a third-pair, power-play specialist? And if the Flyers had a strong indication that Ellis would be spending the 2022-23 season (and possibly far longer) on long-term injured reserve, they would have had about $10.9 million in functional cap room — more than enough for a $9 million Gaudreau, and even another depth RHD to help “replace” Ellis. Perhaps Ethan Bear, for example, who was shipped by Carolina to Vancouver in October 2022 with 18.2 percent contract retention for a fifth-round pick. The Flyers could have even still fit DeAngelo.
So what would have happened if Ristolainen was dealt at last year’s deadline? More draft capital, for starters. The Flyers also would have had an easier path to fitting Gaudreau, though it’s impossible to know if they would have successfully executed the signing. The negatives? Weaker right side depth on defense for 2022-23 and potentially beyond, especially given Ristolainen’s real improvement this season into a defense-first play-driver. Still, that $5.1 million cap hit for four more years is quite a price for that type of blueliner, even if Ristolainen’s improvement is real.
Ah, February 2020. Far simpler times for the Flyers, when the team was one of the hottest in the league, a lock for a playoff berth and seemingly well-positioned for years of contention.
How far they have fallen.
In the lead-up to that deadline, Fletcher and the Flyers were very much “in” on Pageau, in the last year of his contract with Ottawa and in the midst of a breakout season. But Fletcher drew a hard line: he would not be relinquishing a first-round pick for Pageau, unsure he would be able to re-sign and therefore more of a rental for the Flyers. The Islanders, on the other hand, were willing to give up a first, and did see Pageau as more than a rental, quickly signing him to a six-year, $30 million extension.
The Flyers exited the deadline instead with Derek Grant and Nate Thompson. Later that summer, the Isles, with Pageau, took down the Flyers in seven games in Round 2.
So let’s play the “what if?” game. What if Fletcher traded that first-rounder to Ottawa, outbidding the Isles and adding Pageau to the mix? Would they have beaten New York and moved on to the final four?
Honestly, they probably would have. Pageau was a significant contributor to the Isles’ success that postseason, and he scored three goals against the Flyers in the series while helping New York to a strong 55.98 percent xG share at five-on-five when he skated. He helped turn the Isles into a four-line team, with Pageau, Mathew Barzal, Brock Nelson and Casey Cizikas down the middle. Swap Pageau in for Grant, and that’s an enormous swing, especially in a series that went seven games. It’s possible that without Pageau, the Islanders don’t even make it to Round 2, but assuming they did, the swap probably is enough to push the Flyers over the edge.
Would the Flyers have had much of a chance of defeating the eventual Stanley Cup champion Tampa Bay Lightning in the next round, however? That seems highly unlikely.
So would trading for Pageau have been worth it, assuming he would have just been a rental player for the Flyers?
Well, a final four appearance certainly would have been nice for fans. It would have been at least a semi-tangible reward for the Ron Hextall years of retooling in mediocrity, in retrospect the clear high point of all that talent accumulation. And perhaps a longer playoff run in 2020 makes it less likely that the team loses faith in Vigneault’s system and coaching approach over the next two seasons. Or maybe, just maybe, Carter Hart stands on his head against the Lightning to push the Flyers to the Stanley Cup Final, and then they take down a just-OK Stars team to win their third title.
Most likely, however, Fletcher pays a first- and a second-round pick — which ultimately became Tyson Foerster and Emil Andrae — for one more playoff series win and a low-level chance of better future outcomes. Would that have been worth it? Debatable.
What if they didn’t trade: Braydon Coburn (2015)
Let’s rewind the clock back nearly a decade.
The 2014-15 Flyers were going nowhere. Aside from stellar goaltending on the part of Steve Mason, they were an underwhelming club, particularly in terms of skater depth behind Giroux, Jakub Voracek and Wayne Simmonds. So, first-year GM Ron Hextall made the decision to shop longtime top-four defenseman Braydon Coburn.
Coburn wasn’t a rental — he had one more season left on his four-year contract. But Hextall made the decision to sell him anyway, finding a taker in Tampa Bay for a haul on deadline day: 2015 first- and third-round picks, in addition to Radko Gudas.
The trade proved to be a smashing success. Hextall used Tampa’s 2015 first-rounder (in addition to the 2015 second-rounder he acquired by shipping Kimmo Timonen to Chicago) to move up five slots and take Travis Konecny in the ensuing draft. And while the third-round pick — goaltender Matej Tomek — proved to be a non-entity at the NHL level, Gudas was anything but. In fact, over the next four seasons, he dramatically outplayed Coburn, posting 29 Goals Above Replacement for the Flyers (per Evolving-Hockey’s public model) while Coburn managed just 10.3 GAR.
In other words, Hextall upgraded defensemen, and essentially picked up the Flyers’ current best skater as a bonus.
So what if Hextall decided to hang onto Coburn, figuring that his team would be better in 2015-16 and that they would need the veteran blueliner in order to bounce back?
For starters, the Flyers don’t have Konecny right now; it’s difficult to envision a scenario where they jump back into the latter half of the first round in 2015 without an extra first-rounder. They do get at least one more year out of Coburn, however, and it’s fair to note that per GAR, Coburn did significantly outplay Gudas in 2015-16, posting 8.1 GAR to 0.3 for Gudas. The Flyers did indeed bounce back in 2015-16 (Shayne Gostisbehere’s magical season), and Coburn likely would have provided a boost to that club.
But how much of a boost? Assuming that Coburn would have delivered the same value to the Flyers as he did to the Lightning in 2015-16 (a stretch, but let’s roll with it), he would have provided three extra standings points worth of value, per Evolving-Hockey’s formula. That would have given the Flyers 99 on the year — still the least of any Eastern Conference wild-card team. That means that they still would have faced the 120-point Presidents’ Trophy-winning Washington Capitals in Round 1, and probably still lose to that far-superior club.
After 2015-16, Gudas over Coburn becomes a no-brainer edge for the Flyers, who either would have let Coburn leave in free agency, or re-signed a quickly declining player. Gudas, on the other hand, was in his prime, and provided strong on-ice value to the Flyers over the following three seasons, before being shipped out for Matt Niskanen in the summer of 2019. So keeping Coburn means a slightly more competitive 2016 series loss to the Capitals. It also means no Konecny, no Gudas to help the Flyers make the playoffs in 2017-18 and no Niskanen to help Ivan Provorov so much in 2019-20.
Yeah, this was a good trade.
What if they didn’t trade for: Andrew MacDonald (2014)
And now, time for a bad trade.
In the second half of 2013-14, with the Flyers on the road to the playoffs, then-GM Paul Holmgren decided that his defense needed a further boost.
Holmgren, understandably, was still trying desperately to make up for the unexpected loss of Chris Pronger to a career-ending injury. He traded for Nicklas Grossmann in 2012 and signed Mark Streit in 2013. But Holmgren still felt the defense was lacking a mobile top-four minutes eater capable of taking on the toughest minutes.
Infamously, he circled in on Andrew MacDonald as the answer, coughing up a 2015 second-round pick and 2014 third-rounder to acquire the pending UFA defenseman from the Islanders the day before the trade deadline. Then, a little over a month later, Holmgren erased the “pending UFA” status, locking up MacDonald to a six-year, $30 million extension that was an immediate joke in hockey analytics circles and ultimately was viewed similarly by the league at large, if MacDonald’s successful pass through waivers in 2015 was any indication.
The draft picks matter, to a point, because hilariously enough, both players taken with those picks panned out. Brandon Carlo (2015 2nd) became a useful blueliner for the Boston Bruins, and Ilya Sorokin (2014 third) is one of the NHL’s best goalies. But there’s no guarantee that the Flyers would have selected either player had they kept the picks. Plus, Holmgren did essentially recoup the third-rounder just a day later by shipping out excess defenseman Andrej Meszaros to the Bruins. Playing the “what if?” game on those picks isn’t quite fair.
The bigger “what if?” is if MacDonald was never brought in to sign that $30 million contract at all.
MacDonald would ultimately only play out five of the six contract years; he was bought out by Fletcher with one year remaining in the summer of 2019. In those five years, he did provide some value via passable in-zone defense and penalty avoidance. But for the most part, he basically just ate up minutes as a below-average, slightly-above-replacement level top-four NHL defenseman with a knack for dragging down his partners at even strength. The contract can charitably be called a flop and not-so-charitably an abject disaster.
So what happens if MacDonald isn’t acquired at the 2014 deadline, aside from holding onto those two mid-round draft picks?
Holmgren and later Hextall still would have needed to work on the defense — after all, MacDonald did play 272 games across those five seasons, largely on the team’s first or second pair. But the Flyers front office would have had $5 million more in cap dollars during the back half of Giroux’s prime to spend on improving the team. It’s impossible to know which signings and trades could have been possible to add forward depth or legitimately solve the blueline issues, but it’s also very hard not to wonder what would have been behind Door No. 2 as opposed to MacDonald’s Door No. 1. In addition, Fletcher would have had about $2 million more in cap space available in the summer of 2020 — after the Flyers had fallen to the Islanders in Round 2 — to spend absence MacDonald’s remaining buyout charge. That wouldn’t have been insignificant — it’s the difference between $3 million to Erik Gustafsson and having the flexibility to outbid Calgary for Christopher Tanev (cap hit on his deal signed that offseason: $4.5 million).
Now, would $5 million more in cap space have been enough to change the trajectory of Giroux’s age 26 through 30 seasons? Would that extra $2 million have prevented the post-pandemic Flyers from falling off a cliff and ultimately leading to Giroux’s exit?
There’s no way to know for certain. But it couldn’t have hurt.
(Photo: Tim Nwachukwu / Getty Images )