Alright I'm floating a blockbuster here. The instant quick fix for 3 teams involved. (Yes 3 teams!)
https://youtu.be/s3DQg_jtaAw (Insider Trading TSN)
I honestly think there is a solution here where all 3 teams win this. Each pick and player involved is someone that fills an organizational need.
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To Ottawa:
David Rittich (2019 RFA/$800,000) - Potential #1 Goaltender, young.
Micheal Frolik (2 years/$4,300,000) - Veteran Top 6 LW/RW
Oliver Klylington (2 years/ $730,000) - Young Top 4 LHD
Jacob Trouba (RFA 2019/$5,500,000) - Young Top 4 RHD
Calgary 1st (25th - 30th pick)
Winnipeg 3rd round pick
To Winnipeg:
Mark Stone (2019 RFA/$7,350,000) - 1st Line RW, Winnipeg native.
Craig Anderson (2 years/ $4,750,000) - #1 Goaltender, playoff proven.
Michael Backlund (6 years/$5,350,000) - Veteran 2nd Line Center.
Michael Stone (2 years/$3,500,000) - Top 6 D, Winnipeg Native.
To Calgary:
Connor Hellebuyck (6 years/$6,300,000) - #1 Goaltender, Vezina nominated.
Matt Duchene (2019 RFA/$6,000,000) - Scoring top 6 center.
Bobby Ryan (*27% retained to 4 years/ ≈5,350,000) - Veteran Top 6 RW.
Josh Morrissey ( 2 Years/$3,170,000 ) - Strong Top 4 D, Calgary native.
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Optional: Waive Mike Smith
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And to just compare what each team gives up in this:
Spoiler!
Calgary: Rittich, Backlund, Frolik, Stone, 2019 1st, (Smith waived) Lose $1,800,000 in cap space
Winnipeg: Hellebuyck, Morrissey, Trouba, 2020 3rd, (Ryan's Cap Hit $1,950,000 @ 4 years) Lose $4,200,000 in cap space
Ottawa: Stone, Duchene, Ryan, Anderson. Gains $14,680,000 in cap space
Each team gets a combination of a young RFA, at least on player that fits an organizational need, at least a pair of teammates coming from the same team, four roster players, a defenseman and a goalie.
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And this is why I think teach considers this move to some degree.
Spoiler!
Ottawa gets a goalie for the future in Rittich, fellow countryman Frolik signed for 1 more season, 21 year old Oliver Kylington, and two 2019 1st Round picks. Eugene Melnyk sheds a boat load of cap and he can start his rebuild off with serious prospects.
Winnipeg gets a the best player in the deal Mark Stone, Winnipeg boy and replaces Blake Wheeler as captain (when he retires). Playoff veteran goaltender Anderson, Top 6 offensive anchor Michael Backlund and depth D Michael Stone, Winnipeg native, and the brothers are playing together in Winnipeg for a cup run. Winnipeg picks up a goalie.
Calgary gets a #1 Goaltender locked up in Conner Hellebuyck, teammates and top 6 forwards Matt Duchene, and Bobby Ryan, and left handed D Josh Morrissey a Calgary native. Ryan and Duchene also played with another Tkachuk on their LW this season.