I do see Raptors moving one of OG or Siakam. I do want to say that those are two of top available wings. I could see Rockets making a move on of those wings if the Harden rumors were true.
If that package is true, than you're talking Dame-Thybulle-OG-Grant-Nurkic. That drastically improves perimeter defense. But unless you're expecting OG to turn into a premier two-way player, I don't think it raises their ceiling to a contender. I don't know how think that bumps them up that high in standings. I can see that being a #6-8 seed team. Plus they still don't have great depth. Thybulle should be a 7th man off the bench, and you're hoping Sharpe pops.
Honestly if I'm Portland, I'm seriously considering trading Dame and rebuilding. I'm saying that because they're not just a move or two away from contending. They could upgrade both SG and SF spots, and one of those would have to be an elite two way wing. Then, could also upgrade over Nurkic as well. Then still could still upgrade the bench as well. I think it would be more easier and wiser to trade Dame while his value is higher than thinking they can realistically be a contender. The West should be better next year and making a marginal upgrade, would still likely leave them as a play-in team.
Comment