What comes to my scenario (Datsyuk traded and rebuild started at 2014 deadline)
Tampa Bay got 2x 1st round picks + Ryan Callahan for Martin St. Louis.
Ler's expect Yzerman/Holland would have got same trade value for Datsyuk at 2014.
That 2014 NYR 1st turned to be 30.overall, Yzerman traded that down at 2014 draft, getting two 2nds at #35 + #57.overall. Drafted defenceman Dominik Masin and defenceman Jonathan MacDonald with those picks. Both busted.
That 2015 NYR 1st turned to be 28th overall, and again Yzerman traded that down at draft, getting 2nd+3rd as #33 + 72.overalls. Drafted Michell Stephens and Anthony Cirelli with those picks.
Also, 2015 TBL own 1st round pick turned to be 29th overall, and Yzerman traded that 1st + Radgo Gudas + 3rd for Braydon Coburn at trade deadline.
Imo, quite a big overpay for Coburn. They reached the finals, but don't think Coburn was any kind of factor. Anthony Beauvillier was drafted to NYI (after multiple trades between multiple teams, pick ended to NYI) with that Tampa 1st.
Trading Datsyuk for two 1sts + Callahan:
Datsyuk
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Callahan
2014 1st (busting picks Masin + MacDonald)
2015 1st Cirelli + Stephens
So Datsyuk would have converted to 2nd line Center and borderline 4th line Center + cap dump (Callahan).
Lots of variables on the play, but just one example, how these could go.
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And story continues, you don't trade for David Legwand. So you keep Patrick Eaves, Calle Järnkrok + 2nd (Julius Bergman, bust)
Sent out:
Datsyuk
don't get David Legwand
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Got/kept:
Ryan Callahan
Patrick Eaves
Calle Järnkrok
2nd (busting julius Bergman)
2014 1st (busting picks Masin + MacDonald)
2015 1st Cirelli + Stephens