Seems doubtful to me that they'll be able to turn this thing around any time soon. If we could've hit on a Pasta, or a Barzal, or a Mercer seasons ago, they're probably still right in the thick of things. But they were too busy trading those picks away so they could throw shit at a wall and hope it stuck.
I hear you. I get the frustration with the cupboard being so bare with young talent. We have veterans playing well and you wish their was more young to mix with that veteran group. Usually that's a good recipe for success in sports but we just haven't developed young talent or had picks to get young talent in the system.
We took Kapanen in the Pasta draft. Looks bad in hindsight but every team other than Edmonton (Draisaitl) is still kicking themselves over passing on Pasta in that draft. The fact that Pasta fell to 25th overall is just one of those weird league wide scouting blunders.
The pick that became Barzal was obviously lost in the Perron trade. It's hard to say how Barzal would have fit in here though. He's such a pass first type of player and that doesn't always work good with Sid and Geno but Barzal is so talented that he could probably have adjusted his game a bit to fit in here.
That said, there is a price you pay for being a contender. You have to go for it and I think you could argue those moves were worth it. We didn't get Pasta but we swapped Kapanen for Kessel. It sucks to not have a youngish guy like Barzal to extend the window but the pick that became Barzal was traded for Perron and then Perron was traded for Hagelin. That led to HBK and a Cup win. Contenders trade away futures to try to win in that moment and we got two Cups out of those moves. The bill has just started coming due in recent years with Sid and Geno not being able to single handedly carry the team to contender status anymore and no young talent to extend the window and help ease the load that those guys are asked to carry for this team. Pens are in a tough spot but we got 3 Cups and 4 trips to the finals out of these guys. Anything more is just gravy at this point.