If Toronto were to acquire multiple late 1st round pick in a 3-way trade with LA/ORL and/or by trading Barbosa, I expect/hope it is more likely that BC would attempt to move those picks (perhaps along with other assets - ie: Amir, Bayless) for a second lottery pick.
BC wants to "hit the ground running" next season - gutting the team and adding 5 mid-late draft picks is the exact opposite of that. The Raptors are no longer in a rebuilding mode (that is what your plan would be), they are in building mode, which is what turning older players and depth players into a second lottery pick would be.




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