Should Flyers sign Simmonds long-term? It’s complicated

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An NHL GM can make mistakes in a lot of different ways.

One of the most challenging hurdles an executive must clear is determining whether they should keep quality (but aging) mid-level talent around. It’s easy to pinpoint the nucleus of your roster, and try to lock those players down – ideally for value – and it should be easy to disqualify the filler. But what about nice assets with cloudier stances in the pecking order?

It’s maybe a bit amusing that the Flyers signing James van Riemsdyk – a player the Maple Leafs ultimately decided wasn’t a core player – might open the door for Wayne Simmonds to leave Philadelphia under similar circumstances.

Flyers GM Ron Hextall admits that he’d like to keep Simmonds, but he also doesn’t know if it will work out.

“We’d like to sign Simmer,” Hextall said, via Sam Donnellon of the Philadelphia Inquirer. “Whether we can or not, I don’t have the answer to that.”

It’s fair to ask if the Flyers can sign Simmonds. It’s also reasonable to wonder if they should.

Now, if this wasn’t a salary cap league, a big-budget team like the Flyers probably wouldn’t fret about signing Simmonds, who’s an undeniable talent. Things get trickier when the belt tightens, and Hextall’s wise to acknowledge that there are some big decisions – and possibly mammoth raises to brilliant younger talents – coming in the near future.

So let’s explore many of the ins and outs of this situation, and the Flyers’ fascinating outlook with or without one of the league’s best power forwards.

Superb situational scorer

Possessing prolific power-play prowess might sometimes seem like a backhanded compliment (“He can’t score at 5-on-5,” – hypothetical jerks), but it can be highly valuable to unearth players who seem to score in those situations, year-in, and year-out.

Simmonds has been, unquestionably, a fantastic scorer on the power play since being traded to Philly. Since 2011-12 (his first season with the Flyers), Simmonds scored 86 power-play goals, the second-best total in the NHL during that frame. Only superhuman Alex Ovechkin was better, leaping tall buildings with a signal bound at 131 goals; Simmonds leads third-place Steven Stamkos by 10 goals (Stamkos had 76, albeit limited by injuries).

Fixating on the power play is only natural with Simmonds (86 of his 187 goals in 522 Flyers games came on the man advantage), yet he brings other strengths to the table.

While the physical winger’s fantasy value gets bumped up another notch by frequent trips to the penalty box (958 PIM in 762 career NHL regular-season games), Natural Stat Trick’s metrics show that he tends to draw about as many penalties as he takes. So that grit doesn’t necessarily put his team at a massive disadvantage.

Simmonds’ possession stats ebb and flow, but some of that might come down to the quality of his linemates. They were mostly “meh” at even-strength in 2017-18, with Valtteri Filppula and Jordan Weal ranking as his most common forward partners.

Between power plays and normal minutes, the bottom line is that Simmonds has been very productive. Last season’s 24 goals and 46 points were borderline alarming for him for the simple reason that he’s been very, very good at times for the Flyers. Simmonds previously scored at least 28 goals for four straight seasons, and with 24 last year, has five in a row with at least that many. He’s essentially been a 30-ish goal guy for most of his Flyers run, as he managed 15 goals in the 45 contests during the pattern and streak-ruining 2012-13 lockout season.

Long story short, there’s a lot to like about Simmonds. If the Flyers let him walk, plenty of teams will clamor for his services, and there are scenarios where he’d sign with a divisional rival and make his former team miserable.

The questions

Again, there are some stumbling blocks, especially if Simmonds wants serious term.

He’ll turn 30 on Aug. 26. While his rather unusual ability to score in tight might be a skill that actually ages well, there are reasons to also wonder if he’d hit the aging curve especially hard.

Most obviously, a physical player is involved in more demolition derby moments, and even if they “win” those collisions more often than not, they take a toll. (Consider that Scott Stevens retired in large part for health reasons, despite being the guy who was usually the culprit rather than victim of vicious hits.)

[James van Riemsdyk signing could spell end for Simmonds with Flyers]

Simmonds was slowed in 2017-18 by issues that ended up requiring core surgery. Maybe those issues can be considered a one-time thing, but age is a serious question here. With Claude Giroux (30), Jakub Voracek (28), and JVR (29) all signed to serious term and combining for a cap hit of $23.525M, the Flyers already boast some forwards whose contracts could become future problems.

JVR’s skills may also make Simmonds’ PP gifts relatively redundant. During his time with Toronto, 45 of James van Riemsdyk’s 154 goals came on the man advantage.

A clever special teams coach would look at a power play featuring JVR and Simmonds – along with gifted assets such as Giroux and Shayne Gostisbehere – as a buffet of brilliant options. Still, the salary cap sometimes dictates that team give up on luxuries to afford necessities, and JVR might make Simmonds expendable.

The bill’s coming

According to Cap Friendly, the Flyers currently enjoy a robust $13.22M in cap space.

With that in mind, it would be tempting to dismiss the fact that Simmonds is due to make a lot more than his bargain, expiring rate of $3.975M. The issue gets thornier when you consider other looming expenses, particularly if Simmonds – justifiably – seeks both a raise and serious term.

Ivan Provorov is entering a contract year, and Hextall might just want to get that situation wrapped up. The Flyers’ two goalies (Brian Elliott and Michal Neuvirth) will see their combined $5.25M evaporate after 2018-19. One way or another, netminding decisions are coming; it could be a cheap situation once more if Carter Hart ends up being ready, but it’s fuzzy right now.

Locking up the Provorov’s and eventually the Nolan Patrick‘s stand as serious concerns, yet there are also some positives that push the Simmonds decision closer to “go for it.”

Hextall’s been crafty with erasing the mistakes of the past, sometimes quickly and sometimes gradually. Some dead money will be fading soon, making it more plausible for a Simmonds deal to come into focus. Jori Lehtera‘s ghastly $4.7M goes away after next season. Andrew MacDonald‘s ridiculous $5M mercifully expires after 2019-10. They’ll also get to wave goodbye to Dale Weise, Michael Raffl, and Radko Gudas if they want to fairly soon.

Between some money coming off the books and (in an ideal world) another healthy jump for the salary cap, retaining Simmonds might become quite manageable. As Hextall acknowledges, some of the details need to be sorted out.

Wait-and-see?

Donnellon reports that Hextall said he’d be willing to negotiate with Simmonds into the season, and while that might seem like a throwaway detail, it might just be the ticket.

The bottom line is that it will be easier to understand how the pieces fall together (between JVR, Simmonds, and rising young talents such as Patrick and Travis Konecny) after seeing them all in action. JVR’s presence could just as easily boost Simmonds as it could push him to a secondary unit or clog too much of the same real estate in front of the net.

Taking that extra time could also give Hextall the opportunity to achieve cost certainty if he can figure out how much Provorov will cost, and if it would make sense to keep Elliott or Neuvirth around to support Hart.

The Flyers stand as a truly fascinating team to watch. There’s an appealing mix of established players and rising young stars, and if they can come to productive conclusions with the eternal questions about goaltending, they could rise from a playoff bubble team to a frequent, scary contender.

Figuring out what’s the best step to take with Simmonds – whether it be to sign him, let him walk, or trade him before his deal expires – is a very important decision.

For all we know, it could be one of the make-or-break factors as Hextall hopes to convert all of this potential into playoff glories.

James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.