4. Toronto Raptors get established pieces to fit their timeline
Another shooter the Blazers can look into acquiring to compensate for Simons' departure is Gradey Dick. Portland can essentially view this deal as acquiring three first-round picks since the Raptors selected Gradey Dick with last year's No. 13 overall pick. Losing Robert Williams III would be another blow for Portland. Still, the big man's health isn't reliable enough for the Blazers to consider him off-limits, even if he does fit their rebuilding timeline at 26. Williams has played 35 games or less in four of his six NBA seasons.
As mentioned in the Orlando proposed deal involving the No. 18 pick, the Pacers' No. 19 overall pick would be an excellent opportunity for the Blazers to target a big man. Many exciting options should be available in that range despite a weak draft class. They could potentially select Williams' replacement in the form of a younger, cheaper, and healthier backup center.
Due to their contradictory moves, the Raptors' approach to constructing their roster has been unclear in recent seasons. Currently, indications are that they are retooling, but not entirely rebuilding, around 22-year-old Scottie Barnes; this is primarily suggested by their trade with the Knicks for Immanuel Quickley, 25, and RJ Barrett, 24.
Meanwhile, Simons is 25 and would fit nicely with Toronto's retooling timeline. The Raptors need to surround Barnes with as much shooting as possible to complement their franchise player's strengths as a playmaker and weaknesses as a shooter. Simons would be a seamless addition as a combo guard who can give the Raptors more lineup versatility.
Another element of this trade worth mentioning is the financial benefits Portland would get from moving Simons and Williams, especially for players and picks who would all be on their rookie deals. Simons is owed $25,892,857 next season, while Williams is owed $12,428,571. The Blazers would offload over $38 million total for next year, which would get them well under the $171 million luxury tax that is projected for next season.