(author’s note: if you regularly complain about how negative i can be, don’t read this post)

1. Getting Bennett

Given all the different rankings of the top four prospects in the league, it really wouldn’t have been too shocking to anyone if any of those guys went in any particular spot. That Sam Bennett fell to Calgary, though, is perhaps the least surprising because he couldn’t do a pull-up and he’s not a big center like Leon Draisaitl and he’s not a bigger defenseman like Aaron Ekblad.
That this was the No. 4 prospect in the mix is something, I think, that is very good for the Flames. The kid turned 18 just days before he was drafted (he’s a June 20, 1996 birthdate), making him some eight months younger than Draisaitl, seven months younger than Sam Reinhart, and four months younger than Ekblad. In some ways, you have to think that gives him a little extra value, even beyond the fact that he still scored a boatload of points, and led all draft-eligible players in even-strength points per 60 with 3.5. (Draisaitl checked in at 2.9, Reinhart at 2.8.)
This is a very nice get for the Flames at No. 4 because it wouldn’t have been out of the question to take him at No. 1. The team should be very excited, because three years from now, a 1-2 punch down the middle of Bennett and Sean Monahan will probably be very solid indeed.
With that having been said, for the love of god keep him in junior next year. Like, 100 percent, make sure he is back with Kingston next year getting heavier minutes against better competition. Maybe let his strength improve to a place where he can do one (1) pull-up. That’s what should happen.
Again, I know it will never happen. And I know that people think because Monahan scored 22 goals that his being up with the big club for the duration was viewed as a success, but even if you look at it from a strictly-hockey standpoint (and you shouldn’t), you have to consider that his sky-high shooting percentage isn’t going to be replicated now or ever, and his piss-poor possession numbers are only going to continue. On a team that got buried every night in possession, Monahan got buried-er, and that was against some of the softest competition Bob Hartley could find him. Among forwards, only Brian McGrattan had it easier.
I bring this up because if you keep Bennett with the big club for all 82, he’s going to face the same fate. And he’s probably not going to shoot almost 16 percent, so there goes the production angle.
Beyond the hockey-playing, though, there’s also the fact that, as with Monahan last year, you’re burning a year of Bennett’s entry-level deal on a season in which this team is going to be a tire fire. Probably better than last year — mainly because Hiller can’t be as bad as what the clown car in the crease provided last year (but we’ll get to that in a minute) — but let’s say they finish eighth from the bottom of the league. 
What’s the point? And “experience against NHLers” isn’t a valid answer.

2. The rest of the draft

This is why I have significant concerns about Treliving’s ability to make good decisions in player evaluation. As the comparison goes, a potato could have drafted Bennett, and if he works out that’s going to paper over the fact that the rest of the draft was a disaster.
For one thing, you don’t pick a goalie that high. Let alone based on one U-18 tournament, which seems to have been the case with Mason MacDonald. I’ve never seen the kid play — and boy do you hear that a lot about every prospect you think wasn’t worth the pick, as though those naysaying the naysayers all saw Johnny Gaudreau play a few dozen times before he got drafted out of the USHL so now they can say, “See, I knew it.” — but I have seen Thatcher Demko play a bunch and if you’re going to take a goalie there (you shouldn’t), doesn’t it stand to reason that you take the kid who put up better stats playing against grown men than someone who got lit up in the Q? Whatever, it’s dumb to draft a goalie that high, so if you’re basically throwing the pick away regardless, I guess there’s not much of a difference.
Then there’s Hunter Smith who, why waste a pick on a guy who’s big and tough? The Sharks proved yesterday if you want you can get one for real cheap and it doesn’t cost you a shot at controlling the rights to a player who might actually be good one day. The guy can’t score in junior. When your career upside seems to be AHL fourth-liner, maybe don’t waste a second-round pick on him. Ludicrous.
Outside of that, the draft is mostly teams taking fliers on players. If they work out, great. The vast majority of them don’t. Really can’t bother criticizing any of them too much unless they’re Hunter Smith types, because you should never draft guys who can’t score in junior.

3. Signing Hiller

In theory, adding a goalie who’s fairly reliable in his averageness is something that the Flames should have done a long time ago. I am not, however, sure why they did it now.
A thing this team doesn’t need is a 32-year-old goaltender who is going to actually be good. Again, I don’t see the point if he’s still going to get lit up every night, because of how bad the Flames are going to be. They had a goalie, more or less. All they needed was a backup. Karri Ramo posted the exact same save percentage as Jonas Hiller last year, so there’s no real reason to bring aboard a $4.5 million player for two years to do the exact same thing as the guy you’re already paying $2.75 million.
Maybe Ramo regresses a little bit under the weight of more games, but the Flames really couldn’t have asked for much more from him. And moreover, they should want to ask less from him (or Hiller) because the smartest thing they can do right now from an organizational standpoint is be bad. Fans don’t want to hear that but it’s true. Want a better chance at being the future home of Jack Eichel or Connor McDavid? Having a good team save percentage doesn’t help.
A redundant move and little else, probably done for no other reason but to get to the cap floor. That really isn’t the best way to run a team.

4. Signing Engelland and trading for Bollig

Uuuuuuuuuuugggggggggghhhhhhhhhhh wwwwwwwwwwhhhhhhhhhhyyyyyyyyyyyyyyy?

5. Signing Raymond

Now this is a deal I like and I get. Mason Raymond is a good, solid hockey player. He’s coming to his hometown. Nice all around.
He drives play forward pretty well (plus-1.2 corsi relative for his career, which you take). But I have seen him being characterized as a scorer, and if you think that about Mason Raymond I have some bad, bad news for you.
He’s going to put up 40-something points, no doubt about that, but if that’s what you think is even a second-line forward’s production, you’re a little off on that. Since his career began, his points per 60 is in Dave Bolland, Olli Jokinen territory, RJ Umberger territory, and David Legwand territory. In short, not great. Not bad, but he’s not going to drive the bus for you going forward.
I like the signing overall, and I’m glad he got three years, and the money seems more or less correct for a “Please sign here we need help” contract. Fine with it across the board. But a “scorer” isn’t really a good descriptor. On the Flames? Sure, he’ll be like top-3 in points I bet. But not overall.
What I’m saying is: Don’t get your hopes up.