I don't look at Calgary being in a 'win now' mindset. They are in 'stay competitive' mode. I guess if you just look at things either black or white, you would counter that this is just semantics. In my opinion, teams in 'win now' mode generally load up on veterans and sending out futures. This is not what the Flames have been doing for the last couple of years really - outside of the Cammy deal that was a bit more complex.
I personally didn't want the offer sheet to go through on RoR, just because I think the Flames can potentially draft a better player this year for the future, but it definitely didn't scream 'win now' at all. It would if RoR was 32 instead of 22. There is no denying that RoR would have really helped this team in the short AND long term - these are the moves that Feaster has been making.
As for the topic at hand in regards to Kipper, the returns are really tough to project. If the Flames keep 100% of his salary, then it will off-set the cap hit to a contender, making him a further attractive piece to a team like Pittsburgh. I highly doubt Pittsburgh is in the market for a goalie, however. Tampa and Carolina could both be good destinations for him.
As a side note, I would prefer that Kipper get moved to a true contender this year. The guy has been a total workhorse and a big part of this team for practically a decade. Would be really nice to see him win a cup as well.
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