Joined: Apr. 2017
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So, in my mind, I would remove all the potentials that are older than Laine (or not close). No reason to trade someone that young and accomplished for someone older. In many of those cases, you aren't saving much in the cap anyway, and you are shortening the runway to UFA.
After doing that, you are left with:
Hischier - Interesting thought. Cs are worth much more than Ws, but Laine is probably slightly more valuable. Hischier and a B+ prospect/late 2nd round pick might be the equivalent. But, I don't think NJD would do it, their C depth might be one of the best things about their future, and they can get a top W in this draft with 2OA and lock in cost certainty.
Travis Konecny - Slightly older, but close enough. Again, Cs are more valuable, but I think Laine is way better than Konecny, unless Konecny really turns around his trends from the last 2 years for his underlying numbers. It would have to be Konecny, an A prospect, and a pick to start.
Dylan Larkin - Again, slightly older, and a C. No way DET trades its hometown captain. The Illitches don't trade their captains unless they beg them to. They vetoed the Yzerman trade to OTT when Bowman was begging them to do it. Since Steve, all DET captains have been Wings lifers, once they made Larkin the captain that defined the UFA strategy for DET. Larkin is 1 year from UFA as well, so even if you could get him to sign an extension, you aren't saving any money, he'll command at least 8.5m/year. A realistic trade would be close to 1 for 1, but the required Yzerman trade would have DET winning HUGE, something to the effect of Laine + Johnson or Sillinger for Larkin, which is obviously a no-go.
Jordan Kyrou and Robert Thomas - Both interesting names, both in the right age ranges, but would that improve the team? Trades for either of them would be Kyrou/Thomas plus a B+ prospect/2nd round pick for Laine. Each would give you cost savings, and Thomas would add more runway to the UFA timeline.
Matthew Tkachuk - Tkachuk has played 1 more year, but is only slightly older. From an underlying numbers perspective, Tkachuk has more value than Laine, scores at a slightly higher pace (fewer goals, but more assists, and does it with fewer shots and a more sustainable shooting percentage), plays a much tougher game and can play on the defensive side too (does have future Selke consideration in him). Salaries will be about the same (8-8.5M/year). At best, CGY would do it as a 1-for-1 trade, but most likely CLB would have to pay more to get Tkachuk.