If there’s one date on the calendar that contains a lot of Flyers franchise-altering history, it has to be June 23. Over the last 15 or so years, Philadelphia has somehow made moves on that specific date.
A handful of these over the years include the drafting of Nolan Patrick (bad), and years later Matvei Michkov (good). Then there’s the trading of Jeff Carter and Mike Richards within hours of each other, with Philadelphia signing Ilya Bryzgalov hours later that fateful day. Scott Hartnell was on the move one year, as was James Van Riemsdyk and Brayden Schenn, also on various years, but always on June 23. In 2025, Flyers general manager Danny Briere continued that tradition, with Philadelphia acquiring Trevor Zegras from Anaheim while parting with a package that included Ryan Poehling.
Which brings us to the 2026 version of June 23. And what might happen with the organization this coming Tuesday. While there could be a variety of scenarios that play out with the club, there are a few frontrunners when it comes to resigning players with contract extensions, or possibly parting with them in a trade scenario. Here then, in order of leading candidates, is a list of some possibilities that might transpire on Tuesday. (Note: Because Dan Vladar remains under contract and has a year and a few days remaining on his current two-year deal, the Flyers can’t announce a possible extension until July 1.)
1) A Trevor Zegras extension
We won’t know the term and the number until it’s finalized, but it seems likely that the Flyers and forward Trevor Zegras are going to be partners for a good chunk of his future playing career. Zegras’ first year made a great impression on the club, and the club made a great impression on “Ziggy.” A bright spot on an awful power play, Zegras started the season at wing but the transition to center was rather strong, albeit with a few hiccups. The fact the move was made during the homestretch, when the Flyers were seemingly out of the playoff race, made it a low-risk move. But Zegras and the team came alive, and Zegras became more comfortable playing down the middle.
It would be safe to say that the deal is probably going to be in the $8 million range in terms of average annual value, and it’s probably also safe to say it will be north of six or seven years. Zegras would also most likely be given some clauses when it comes to no movement or no trade, at least for the first few seasons. It would be another piece of the Flyers puzzle locked up for the foreseeable future. And perhaps a good bit of business done by Philadelphia general manager Danny Briere given the rise in the salary cap and a short-term deal might cost the club more in the bigger picture down the road.
2) A Jamie Drysdale extension
It might be the antithesis of the Carter/Richards transactions if Philadelphia announced that Zegras and his good friend Jamie Drysdale were extended on Tuesday. Drysdale won’t cost the Flyers nearly as much as Zegras, and they would probably be reluctant to give him anything longer than five years on a new deal. The blueliner looked like a deer in the headlights on arriving from Anaheim after the Flyers and William Gauthier couldn’t work things out. It took some time for him to adjust to the new team and new expectations.
Over the last two seasons though, Drysdale took a step forward, looking far more confident than at any time in his tenure with Philadelphia. And finding a secure spot in the top four alongside Cam York. Drysdale appears to be beyond his injury-plagued seasons, and is looking forward to taking another step into being a quality, dependable, minute-munching defender the Flyers can rely on for a handful of years to come.
3) A Rasmus Ristolainen trade
With one year left on the five-year contract Chuck Fletcher signed him to, Flyers defenseman Rasmus Ristolainen looks like he could be on the trading block. The question is where Ristolainen might end up, and if the Flyers can get a first-round pick or a prospect in return, then it will be another bit of business done by Briere. It turned out to be a blessing in disguise when Philadelphia kept him at the trade deadline as he was another key piece in keeping the Flyers heading in the right direction towards the third seed in the Metropolitan Division. But it would be rather risky to see Ristolainen at this year’s training camp, especially when he’s still healthy and can be dealt before either the trade deadline or a lengthy injury.
Ottawa has been linked to him but there are others who might find him to be the right piece. This is particularly true because it’s a one-year deal, so it’s not a huge albatross hanging over a team should they trade for his services and he doesn’t deliver. And, as previously mentioned, Ristolainen’s contract is far and away less risky than the likes of acquiring Darnell Nurse or Toronto blueliner Morgan Rielly and their respective deals.
Considering as well the fact Ristolainen might be impeding on Philadelphia moving forward with younger (and cheaper) defensemen like Oliver Bonk, Hunter McDonald, or David Jiricek (who has to clear waivers should he not make the club after training camp), it might be time to see Ristolainen the door so the Flyers can move forward. On the whole, Ristolainen had his game completely revamped by former coach John Tortorella and his staff. He might take that game elsewhere with the Flyers reaping some rewards.
4) An Owen Tippett trade
Owen Tippett has six more years left on a contract that, if he continues to develop and flourish as he did the last two seasons, will be a steal for the majority of it. At an average annual value of $6.2 million on a contract that expires in 2031-32, the winger is looking like a player who has the talent, speed, and mindset to take over a game and change its course with one shift. Tippett, who had internal bleeding which saw him miss all four games of the second round against the Canes, tied his career high in goals (28) and ended up with 51 points.
The question then is why would Philadelphia trade a forward who can score, can skate, can change a game, has missed a combined 15 games the last four regular seasons, and is on a contract that could make the Flyers look like geniuses, trade Owen Tippett? Well, if there’s a chance the team can secure a need that helps them now and in the future years, then it’s something that has to be considered. Seeing Tippett go but having a top-end center coming back might be the price required to pay. A top-pairing blueliner who can quarterback a power play effectively might also see Tippett going. It’s a forward you’d hate to see go, but one that been talked about in circles for some time.
5) A Nick Seeler trade
This seems to be unlikely, but, like Ristolainen, Seeler might be seen as a player the Flyers can ship off to create a spot for another younger blueliner. The trading of Emil Andrae (and addition of Simon Benoit) didn’t really solve any possible logjam being one coming and one going. Seeler, who turned 33 earlier this month, has two years left on his four-year deal worth $2.7 million per year on the cap. He didn’t have a standout season, mainly because he was part of a far sounder defensive structure that didn’t need Seeler playing the role of a second goalie on the ice. But he wasn’t a liability out there either, doing what he usually does on the third pairing while being a quiet policeman for the club.
Again, Seeler wouldn’t command a huge amount in return, but could be part of a package to land more depth up front (and down the middle) should a center be on the trading block. Another possibility is seeing Seeler part of a package during the NHL Draft that sees Philadelphia moving up from the twenty-first spot to land an asset they’re seeking. It’s probably the longest shot of the five mentioned thus far, but there’s always a chance.
Stats courtesy of HockeyDB.com and Capwages.com.
