The Blazers are probably seeking a package featuring multiple first-round picks and promising young prospects. Their return for Lillard currently features only one first-round pick and two pick swaps from Milwaukee, as well as Deandre Ayton. Clearly, their return is incomplete as they need to convert Holiday into future draft picks and players that fit their timeline.
As far as first-round picks, it’s unclear if they’re seeking quantity or what they perceive as quality. Meaning, do they want the most amount of picks they could possibly get, or do they want particular draft picks that they think could end up being high selections? For example, they could be weighing offers featuring a contending team’s next few first-round picks versus those with one that is far out in the future.
If the Blazers can acquire a certain type of player for Holiday, it would ideally be a forward. Their backcourt of the future is set with Scoot Henderson and Shaedon Sharpe, and Ayton is as good a starting center a team could wish for. Their top forwards include Jerami Grant, Matisse Thybulle, and Kris Murray, but Grant doesn’t fit into their plans anymore, and neither of the latter players projects to be high-end starting caliber players.
Below is a list of several teams that could use Holiday and make a reasonable offer for him.