I think during the season, but that depends on how well Matheson and Jankowski play.
Even if Jank is playing well, I just get vibes of 2018 here. Is JR really going to be happy going into the playoffs, in one of the few remaining years with Crosby, Letang and Malkin still both as elite players, with Jankowski as his 3C? I think the ED has to be considered, but winning now is more important than good asset management with the ED.
All take 2018 compared to the last few years. In that 2018 most experts thought we had a good chance to 3peat going into those playoffs. We lost to the eventual Cup Champs which was no shame in that. We had several game 7 wins in 2016 and 2017. It is just a matter of getting a few bounces go your way that is the difference between those years. The main factor was that Murray was outplayed badly in that Caps series and that wasn't the case with our goaltending during those Cup wins.
I really don't see any comparison to the 2018 team and this team is built much more like the 2016 team but even faster and more skilled wingers now and a good chance of having a better defense group. It will all come down to goaltending as usual when it comes to the playoffs. This team has the horses to cause opposing defenseman fits with the speed on the forecheck with this winger group. Not only is this wing group faster than 2016 but also more skilled.
We haven't had wingers like this for our top 6 since the 90's. Even that 2016 team had Sheary and an old and declining Kunitz on the top line. The 2nd line was not much better with Rust as a rookie and not near the point getter he is now and Hornqvist who is a great net front presence guy but nobody even back then would call him a fast skilled forward. Hornqvist was the only winger you could make a case for that was a top two line winger. Comparing that group to Guentzel, Zucker, Rust, and Kapanen now is night and day both with speed and skill. That 2016 team had Kessel on the 3rd line but Hagelin was nothing more than a good 3rd line winger himself. So Pens had a dominant team with literally 2 wingers of top two line ability with one of those playing on the 3rd line and the other in Hornqvist who well deserving of being called a top 6 didn't exactly bring skill and speed.
Every team has its holes so we will just have to see how this group works. I contend this team is built to play Sullivan's system better than any team we ever assembled. Time will tell if I am right but no doubt we have the wingers to keep a constant forecheck pressure offense.
No matter if this team fails to win a Cup it is going to be one of my favorites to watch since that 2016 group. That group was so much fun how they kept a constant forecheck. I rather lose with that system than win a Cup playing old NJ style.