So your master plan to rebuild is obtain future 1st rd picks from MIL and hope Kryie leaves and Giannis doesn't still take them to the playoffs?
Then turn around and some how pry Cousin's expiring contract away from NOP for an expiring contract?
Why not just use your most valuable asset and get Cousins in the first place?
CLE gets Cousins and Middleton
MIL gets Holiday and Frye's expiring contract
NOP gets Kryie and Monroe's expiring contract
Sure you miss out on all those valuable 2020+ early 20th picks from MIL but you might convince Lebron to stay a little longer.
Lebron is gone. He's out.
Why would Milwaukee do that? They are a small market team and Holiday is earning huge money and hasn't really done all that much to prove he is elite. Milwaukee cant afford contracts like those.
Expiring contracts are useful for a team like the Lakers who will then have more room to sign players next summer.
Cavs are in the luxury tax, an expiring contract does not buy them any space to sign a new big contract next summer.
You are essentially saying Cavs should trade Kyrie, a superstar, for 3 mediocre non-lottery picks. Which is absolutely godawful return.
I'm essentially saying that Lebron is gone. Cleveland have 125M next year committed to 9 players including Lebron. That becomes 90M to 8 players should Lebron leave. That would give Cleveland roughly 10M in cap room to try and move forward post Lebron.
Having someone like Monroe or Boogie expire would take that to 75M in committed salaries. That gives Cleveland approximately 28M in cap space for the 2018/19 season assuming the 103M cap projection is accurate.
This leaves cleveland with 3 possible scenarios
1. Lebron changes his mind and decides to stay. Cleveland now have Lebron, Monroe/Boogie, Warren and Bledsoe as their best 4 players, all can create for others and shoot.
2. Lebron leaves Cleveland has Bledsoe Smith Warren Thompson and Monroe/Boogie as the starting 5 and stays a perenial playoff team in the east for the next 5 years because they are able to add talent via the non taxpayer MLE and the picks collected from Milwaukee can be used as trade assets.
3. Lebron and Monroe/Boogie both leave for nothing.
Cleveland has 28M in cap space, 3 promising young/prime players who will be worth something on the trade market hypothetically (Bledsoe, Warren and Thompson) and two first round draft picks per draft for the next 3 years. They will also likely have a big expiring contract like Jared Dudley or Tyson Chandler.
This means that Cleveland can take on up to 40M in bad contracts for picks/assets while tanking for the next 3 seasons and they will be ready to be a contender post Lebron within 3 years or less provided they don't screw up the rebuild.
All of those scenarios are good for Cleveland.