While none of those 3 deals are going to win awards for best bang for your buck none of the deals are crippling deals that have prevented us from signing, trading for or adding anyone so it is hard to be overly critical of them.
Engelland- I really don't get how this was a bad signing unless you think that teams need 6 #1 guys to play on the team. He was signed to be the 6th defenseman and provide the team with tougness and character and to me he has done that very well, stepping up last year when needed as well. He was a better option than anyone else last year in the 6th role and this year as well is better than anyone else to fill in on the bottom pairing. He is a big step up from Smid and showed this year he is better in the short term than a young guy like Kulak.
Last year the Hawks won the cup basically not playing with a 6th defenseman and a times a 5th guy, They would have loved to have a guy like Endgelland to fill those roles on their team but didn't have the cap. Calgary did so good for them to have him on their team.
Raymond- Not a great signing now but he isn't holding anyone back. The team can afford to sit him and play a young if it is warranted but so far nobody has stepped up to out play him. I think had the team known that Jooris, Bouma, Ferland were all going to take the steps that they were they likely don't make this move but at the time it looked like the team needed some secondary scoring.
Ramo- This to me is the worst of the 3 not because it hurts us in terms of the cap or stops the team from doing anything but because it doesn't make any sense to me and not just because I am not a fan of Ramo. If you didn't think Ortio was ready to be a back-up that's fine but there are/were plenty of guys available to fill that role- Scrivens, Budaj, Tokarski- are three off the top of my head that could have been fine fill in back-ups if Ortio struggled. If you didn't think Hiller was good enough to be a starter, well Ramo does nothing to improve that situation as he has continually showed he isn't good enough either. I guess there is a small chance that a 29 year old guy all of a sudden "gets it" but that seems unlikely and certainly not worth overpaying to have him on the team when you already have two options that are at worst as good and likely both better than him.
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