Which risks will Chuck Fletcher be willing to take coming out of this offseason?

As the Flyers approach the offseason with some limited flexibility, they’re going to have to take some chances. It’s up to Chuck Fletcher to take the right ones.

As we sit and ponder what this Flyers team is going to do this offseason, there’s a question that the folks in the front office need to be thinking about and deciding as they try and draw up their perfect offseason: what risks are they willing to take?

The reality is that every team, especially right now in the time of a flat salary cap, has to take some risks and some chances in putting together a team. Now, those risks can be and are very different depending on the circumstances a team is facing. Maybe you’ve gotta take the risk that a key piece who had a bad year last year is going to bounce back. Or that the guy you got on the third day of free agency for a one-year deal can fill a legitimate role for your team. Or that all of your young players are just going to take a step forward at the same time. Or that you’ll be able to get away with flagrant cap circumvention without the league doing anything about it.

Similarly, the impact of those risks and chances depends a lot on the team. If every risk and chance that the Ottawa Senators took last offseason worked out this past year? They’d probably still not be very good, though surely better than they were. Similarly, if every bet Tampa took last offseason blew up in their face? They’re probably still a playoff team, even if they aren’t the obvious Cup contender we still know them as.

For most teams in the middle of the league, though, how those risks work out largely dictate the direction of their season. And that brings us, of course, to your, my, and our Philadelphia Flyers.

In his first offseason running this team, Chuck Fletcher made a few bets. He guessed that two veteran defensemen who had good track records but struggled the previous season would be able to rebound. He thought going out and making an aggressive move for a second-line center would make the rest of the forward lineup fall into place. And in maybe his biggest bet of all — months after being hired to replace a guy who was fired in no small part because he didn’t seem to want to mess with this group of players — he more or less said that he thinks this group of players can compete if he just gets them a bit of help.

Those bets? They hit. Nearly all of them. And the Flyers enjoyed their best regular season in about a decade.

A bit over a year later, at the helm of a team that looked to be on the fringe of Stanley Cup contention, Fletcher again had to take a few risks. He bet that his group on defense, minus its top-pair right defenseman from the year before, would be able to hold up, or at least stay steady long enough to hang on until he could acquire reinforcements during the season. He guessed that young guys that had career years or breakouts in 2019-20 would be able to build upon them in 2020-21, and that the two young forwards that had to deal with life-changing illnesses the year prior would be able to step in and get back to where they need to be, and that the young goalie would be good enough that the team didn’t need to invest much in a backup plan.

But the biggest risk he took was the quietest one, the one that tied all of those smaller ones together: the risk that things were going to work out.

From last October, about a week into free agency, at which point it was clear that the Flyers were not going to be big players in the offseason:

[Y]es, every team has questions. But I can’t shake the feeling that there are more “what if this thing that was good last year goes wrong this year” questions than there are vice-versa when it comes to this team.

Now, if the answers to all of these questions end up being positive ones? Well, this team’s a Cup contender. Hands down. But holding on to the possibility that everything — or even close to everything — that you need to go right will break your way? That’s taking a risk. A different kind of risk than, say, giving out a big contract to a defenseman in free agency or via a trade acquisition, and one that’s less directly obvious. But it is a risk. And as much as adding a no-doubt reinforcement via free agency or trade (one who, with due respect to Erik Gustafsson, is better than Erik Gustafsson) may add some long-term risk, a guy who can wipe out a question mark or two that currently exists with this team helps eliminate some short-term risk, and that’s what the Flyers are missing out on by essentially sitting out the offseason.

The risk the Flyers took last offseason was that they didn’t need to take one.

And that burned them. Real bad. Every coin they flipped that came up heads in 2019-20 came up tails a year later. If there was a question about anything or anyone other than Joel Farabee, James van Riemsdyk, and maybe Claude Giroux, that question came up with an answer far below what any of us were hoping for.

And as such, for the third straight offseason, Chuck Fletcher is going to have to ask what risks he’s comfortable bringing with him into the 2021-22 season.

The Flyers are in a decent position. Not a truly enviable one, where they’ve got long-term cap flexibility and a young roster already in serious contention. Not a catastrophic one, where their whole team is over the hill and they’re capped out for the next half-decade. A decent one. Some young players that have flashed talent, some old players that still have something in the tank, and a bit of cap flexibility. You do not have to work your imagination muscles very much to end up with a team that is better than what this past year was (perhaps not having the worst team-level goaltending of the salary cap era would help there), even if the team just re-signed its RFAs and made some minor adds in what we could call a fairly low-risk offseason.

Of course, the goal here isn’t to be better than last season, it’s to put together a team that can make actual noise and contend. And to do that, in this environment where cap space is going to be tough to find and so many young players are coming off down years, you’re going to have to take some risks. Even beyond the inevitable ones that they’re already taking that their young players are going to be able to bounce back, the Flyers are going to have to really take a chance or two or several to put together the team they’re hoping to, and those moves are going to have consequences and risks.

Maybe you want to dump off James van Riemsdyk and/or Jakub Voracek in a trade to clear out cap space to make a big add. Cool, that makes sense ... buuuuuuuuut you’re going to have to find a way to replace those guys’ scoring, and there’s no obvious internal candidates for those jobs. Got your eyes on a prized defenseman in free agency? One Doug Hamilton, perhaps? Love it. Absolutely go for it. But if your offseason is building up to that, and you wait as other candidates come off the board or get traded to/sign with other teams, you better be real sure you’re going to get him, or have a solid, adequate backup plan if you don’t.

Those are just two examples of things that I would honestly love this team to do, yet they’re going to create issues. Maybe those issues are worth it, and the Flyers are willing to handle one or two more question marks in their forward group (another rookie? A bargain-bin free agent?) if it means that they can bring home the defenseman they want to get. What risks are Fletcher willing to tolerate in order to get what he needs to, and which ones will have to put his foot down on and say he can’t go for?

That, as much as anything, is the question of this offseason for him and for this franchise. It’s an extraordinarily tight rope to walk, and I don’t envy Fletcher for having to do it, but then again, maybe if he’d done it better last offseason he wouldn’t have to this time around.