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The James van Riemsdyk signing represents a step forward for Ron Hextall

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It took a while, but in his fifth offseason in charge of the Flyers, Hextall finally made a move with the clear message that this team is ready to start winning games.

Boston Bruins v Philadelphia Flyers Photo by Al Bello/Getty Images

Where do you see yourself in five years?

Many of us have probably asked or been asked that question at some point in our lives. Five years has become the arbitrary future timeframe through which we’re often asked to try and plan our lives. It’s a period of time in which a lot can change, yet one that’s short enough where you can reasonably try and plot out where you’ll be when it elapses.

Ron Hextall, who took over as general manager of the Flyers a week after their 2014 postseason ended, is in his fifth offseason as general manager of the Flyers. In that offseason, he inherited from Paul Holmgren a situation that was largely unenviable: an average, aging, and expensive roster, with one of the worst defenses in the NHL and a largely barren group of prospects.

There were a few possible directions that Hextall could have gone from there. Double down, get aggressive, and try and make more moves to contend with young stars like Claude Giroux and Jakub Voracek entering their primes? Or blow it up and start from scratch, knowing how long it would take for the team to be in a legitimately good long-term position again?

Hextall has tried to thread the needle between those two endpoints. The Flyers haven’t tanked, and have never managed its roster like a team that didn’t care about the present. But at the same time, the Flyers under Hextall have mostly refrained from making moves. Not just big moves — moves, period. Call it conservative, call it risk-averse, call it slow, call it safe — call it whatever you want. It’s felt like, above all, the past few years have been about avoiding the possibility of making a big mistake.

That’s not to say there haven’t been mistakes, but they’ve largely avoided problems, so to speak. Dale Weise’s contract signed two years ago today has been bad, but at $2.35 million a year that’s more of a nuisance than a disaster. The decision to trade for Valtteri Filppula at the 2017 trade deadline in hopes of finding a short-term middle-six center didn’t work out (well, depending on who you ask), but that was a one-year rental that didn’t block anyone of significance. The move this past February to get Petr Mrazek when basically every other goalie was injured largely failed, but the Flyers still got into the playoffs and few expected Mrazek to be anything more than a pure rental, plus goaltending in a two-month sample is kind of a crapshoot anyways.

But while the losses haven’t been bad ones, the wins haven’t been particularly victorious ones, either. In fact, it’s hard to point to many real meaningful wins in terms of NHL-level acquisitions during Hextall’s tenure as general manager. Radko Gudas has probably been the team’s most successful acquisition of the past four years, and somewhat ironically, he was a throw-in in a sell-off trade where Braydon Coburn was sent to Tampa.

For the past four years, the Flyers have largely made small strokes while they waited for Hextall to replenish the farm system. On that front, Hextall has objectively done a good job. The Flyers had what was widely seen as the top-ranked prospect pipeline in the league as recently as last summer, and they’ve still got depth on the way at basically every position even after about a half-dozen graduations in the past few seasons. This is outstanding, and consistently having good young players available is crucial to maintaining success in a salary cap league.

Yet it’s hard to just wait the requisite amount of time for a bunch of young players to prove that they’re NHL-ready and then grow familiar with the NHL itself. It’s especially hard to do that when those young, prime-age stars that were there when Hextall took over will be 29 and 30 years old when the puck drops on next season. And as exciting as it’s been to see guys like Shayne Gostisbehere, Ivan Provorov, and Travis Konecny emerge onto the NHL scene in the past few years, it’s hard to really keep a fanbase’s attention and confidence when the on-ice product is basically about the same average quality right now as it was when you first took over four years ago. Far too often, it’s felt like the actual urgency to win games in the here and now just wasn’t there.

The way Hextall’s talked about this team in his time here, it’d have been reasonable for fans to wonder if the team would really ever try and make big moves. Hextall’s proud of the work he’s done to replenish the pipeline, as he should be. And in his defense, until this offseason, cap space has been pretty tight ever since he arrived here, largely thanks to contracts signed by his predecessor, so to some extent his hands have been tied at the NHL level. But rarely do teams draft, develop, and plan well enough to simply succeed by doing that alone. Because doing that alone just takes a really long time. That doesn’t mean it can’t work out! This year’s Winnipeg Jets finally broke through after more or less a decade’s worth of inaction beyond drafting and the occasional trade. Hopefully there’s some wisdom to his methods (or what have appeared to be his methods), and several years from now we’ll have a perennially competitive team that will make all the waiting feel worth it.

But even if we ignore the fact that waiting is a drag and team ownership doesn’t always have the patience to wait as long as it takes, the Flyers don’t have the privilege to just totally wait out their young players. Not anymore. Not after a season in which Claude Giroux drops 102 points, Jakub Voracek sets a career-high in scoring, and Sean Couturier is a runner-up for the damn Selke Trophy. These are guys in or exiting their primes, who are getting paid like guys that should be anchoring a legitimate contender (Couturier and his fantastic contract excepted). This is the time where you say that “we owe it to ourselves, to our top players, and even to our fans to take a shot.”

This is the time where you go and sign the second-best forward in free agency to a five-year, $35 million deal, the way that the Flyers are reportedly planning to with old friend James van Riemsdyk later today.

At first glance, this sure feels like a step out of the comfort zone for Ron Hextall. Not just based on his actions over the past four years, but based on his words. You could probably find a handful of quotes just like this one over the past few years, but here’s what Hextall had to say about free agency in his first summer with the Flyers:

To be honest with you, July 1 is one of those days where we all can get carried away. I look on my board here and look at our team, and we’ve got a good team. Sometimes this day, you make some of the poorest decisions you make, and quite honestly we didn’t have to think it through that hard.

This is the day where a lot of times you do something and you have buyer’s remorse. But it’s hard. You have a lot of holes to fill. Back in LA a few years ago, we were in that position where we had a lot of holes to fill, and it’s hard to fill all your holes in a cap world in free agency. Again, it’s one of those days where sometimes you look back and you did something good -- I think there’s some good buys in the market -- but there’s some other ones that are inflated.

To be clear: there’s a lot of truth in those two paragraphs. Teams make bad decisions in free agency every year. Some teams will inevitably make bad decisions later today.

But it’s July 1, and the Flyers — thanks to their having a strong core, a good group of prospects, and ample cap room — are now in a position where they can and should be willing to risk having buyer’s remorse with the right reward there for the buying. And Ron Hextall, for the first time as general manager of the Flyers, has pushed his chips in for a marquee acquisition, one that years from now people will point to as either a big win or a problem depending on how things go from here.

With due respect to the other moves he’s made, this is truly the first thing Hextall has done that has sent a clear signal to everyone paying attention that we are going to go out there and win as many games as we possibly can next year. Sure, young guys will continue to filter in and learn the ropes once they’re ready, as they should. But you don’t go out and spend $35 million on a 29-year old winger if you’re content with winning 42 games, making the playoffs on the last day of the season, and losing in the first round. You do this because you know it’s time to stop slow-playing it and win something meaningful.

Perhaps Hextall was just waiting for the right moment to flip the switch. After all, the acquisition makes complete sense if we’re willing to put aside the awkward history between the Flyers and van Riemsdyk. He fills in a hole on the left wing and is a shoot-first player who fits perfectly with the team’s current forward personnel. Maybe this was just the first time where a move like this truly made sense between the combination of cap space and talent available.

Perhaps, though, Hextall wanted to ensure that this team was going to be better five years into his tenure than it was when he took over. Maybe he felt the pressure — from owners, from fans, from his leadership core, from himself. Who knows. But in year five of Hextall’s tenure, the expectations surrounding his team are finally going to be there. Maybe more moves of significance are coming today and later in the offseason to further drive home that point, or maybe this was the one that Hextall felt made the most sense and the promotions from within will continue at places like third-pair defenseman and third-line center. We’ll see.

All we know is that Ron Hextall isn’t going to be happy if, at the end of his fifth season, this team is only as good as it was last year, which is only as good as it was when he got here. The Flyers are really starting to go for it. And that, believe it or not, is a big step forward.