Depends a lot on how the board shapes up. Personally, my 2 targets at 4 are Risacher and Castle. If both of them are projected to go top 3, I might consider moving up if the price is reasonable (say, future lottery protected first a few years down the road). If those 2 are gone, I'd definitely consider all options for trading back or out, I'd probably do 4 for 7+14 with Portland, as for Chicago I do see them as very interesting trade partners because of the protections on the owed '25 pick. Say, move back to 11 in exchange for them unprotecting their '25 pick, or make it top 2 protected but add a '26 or '27 pick swap, or something Presti-esque to that effect.

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