I don't think Hamilton will be really bad, we're still keeping Strome, Saigeon, Kaliyev, Donofrio (who has been decent), Gleason and Mattinen and decent odds of getting Thomas back. Certainly not cup contenders, but I think there's enough still there to avoid an early exit. The is especially true with the state of Kingston, Missy and Sudbury and Peterborough still rebuilding. I'm expecting a squeak into the playoffs season with a big sell happening at the deadline.
The season after next will likely be really bad though, little doubt of that. The team just doesn't have enough picks right now to make a splash and I don't think they are going to get enough immediate returns back next year.
True. But you can imagine Staios will be preparing for a full blown selloff as soon as this season is up, Memorial Cup or not. And you left out Entwistle.
The problem for Hamilton is the defense (who's going to play defense?) and the goaltending (Donofrio barely played and isn't trusted by Gruden and will likely be traded similar to Ceci as he's not part of the Bulldogs future, Zachary Roy's raw and unproven, Costantini will likely be with the Hamilton Kilty B's (formerly the Ancaster Avalanche) or somewhere as he won't be an option until 2019.)
Thomas is highly unlikely to return unfortunately--St. Louis' depth in centre is very thin, plus being a first rounder, has a strong chance of making the Blues.
Saigeon is 100% gone--AHL eligible and expected to be drafted, and his strong season and playoffs means an OA year is basically out of the question, similar to what happened with Matt Luff.
Mattinen is also 100% likely to not return--he'll be on the Marlies or ECHL next year as he'll likely go pro (AHL eligible)
Ben Gleason is 50/50.. depends if he gets drafted.
Strome and Kaliyev are the only ones returning for sure (unless Strome really impresses the Flyers, though he's likely looking at one more OHL season.)
And as you said, once the 99's graduate--this Bulldogs team is in serious trouble. After Kaliyev, the cupboards are very bare.. even if they make the playoffs next season, it'll be a one-and-done, as they'll likely get matched up vs. a top team (Oshawa? Barrie? Ottawa? Niagara?).. and they need to sell quickly--don't end up like what happened to Guelph, who waited too long to rebuild after their Memorial Cup run, and ended up with a devastating plunge which the franchise is still trying to recover from--don't want to see this happen to Hamilton, especially if they decide to bid for a Memorial Cup in 2021 (pending a new arena).