Does this trade make sense for the Portland Trail Blazers?

Trading CJ McCollum is definitely an option for the Trail Blazers this offseason in search of adding more talent to their roster and this trade certainly gives them the means of doing so. OG Anunoby, Chris Boucher and the 4th overall selection in the 2021 NBA Draft gives the Trail Blazers three talented players who can contribute immediately, but they can probably get even more value for McCollum from another team. 

There have been discussions featured in trade rumors so far in the NBA offseason between Philadelphia and Portland regarding Ben Simmons, so maybe holding onto McCollum gives the Blazers a chance to add another All-Star talent in Simmons. Boucher and Anunoby are not All-Star talents and while a player like Jalen Suggs or Jonathan Kuminga at 4th overall could be an All-Star talent in the future, Portland needs to win right now. 

Damian Lillard is remaining “loyal” to the Trail Blazers, but based on his latest comments, Portland seems to be running out of time. Lillard wants to win right now and while trading McCollum to Toronto does give them a ton of assets, do any of these players really change the fate of the Blazers in terms of being true contenders? 

Portland is not going to become a championship team overnight, which is why holding onto CJ McCollum and trying to add another, third high-level talent is more likely for the Trail Blazers. Even if the do end up trading McCollum, they can definitely get an All-Star-like talent for him, which is something they would not get from the Raptors. 

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This trade really does not make much sense for the Trail Blazers to make this offseason, unless they can see the writing on the wall that Dame is going to leave. Given how everything has played out, Lillard is not going to be in Portland much longer, which is why they could very well just blow everything up now and start their rebuilding process a year before it will likely begin. 

Time has seemed to run out the Portland Trail Blazers with Damian Lillard growing restless, which is why at the end of the day, this trade could be a very enticing offer for them. Adding young talents and a high-level prospect with the 4th overall pick is a lot of value to say no to, which is why Portland leveraging C.J. McCollum seems more and more likely this offseason.