If the Caps were willing to solve Edmonton's complete lack of goal scoring wings that cheaply, Edmonton would have made this trade months ago. Connolly was a UFA two years ago, but so was Eric Staal, and the Wild traded a couple great young players to avoid losing Staal (okay, or some other guys, but I would've picked Staal) in the expansion draft. Player value fluctuates with performance. Connelly has back to back 15 goal seasons and a Stanley Cup ring. He would be the Oilers' best goal scoring wing right now who isn't actually a center. Definitely fits into the Oilers' top six, somewhere.
I'm not opposed to the lineup above, but I think Connolly is worth Dracacula (
https://www.hockey-reference.com/teams/CGY/2018.html). I'd even throw in Barber for a 4th round pick to get it done.
The down side of bringing up Gersich right away is that then you have one less replacement ready to come up from Hershey after next summer's salary cap crunch, in case Vrana, Burakovsky, and Djoos each has a big year, offensively. If Gersich also scores 20 goals... half those guys are gone. But if Gersich scores 30 goals in the AHL, he still comes up to the NHL next year, at less than 1M. Yes, moving them up early will give someone else time to develop in the AHL, but the Bears missed the playoffs last year. They need more help than the Caps right now. I mean.... unless all those UFAs they added this summer are enough to put them back in the postseason alone?