2. San Antonio Spurs add a better fit for Wemby
OR
Similarly to the Magic, the Spurs make a lot of sense as a potential offseason trade partner with the Blazers. A deal centered around Keldon Johnson in exchange for one of Portland's guards, either Simons or Malcolm Brogdon, could benefit both parties. The Blazers have a stockpile of guards and could be interested in a well-rounded forward like Johnson to balance their roster better.
Meanwhile, the Spurs desperately need a playmaking guard to get Wembanyama as much help as possible. Simons would be intriguing for San Antonio due to his elite shooting, making it more difficult for teams to double-team Wemby. Because Simons is perceived to have more trade value than Johnson, it makes sense to swap either of the team's two lottery picks in this upcoming draft.
At No. 4, the Blazers could potentially get Donovan Clingan, who they supposedly are high on. If they decided to trade up for No. 8 instead, Portland could take two back-to-back high upside swings. Some possible prospects include Ron Holland, Cody Williams, or Tidjane Saluan, none of which are guaranteed to still be around at the end of the lottery, especially in this unpredictable draft.
Ultimately, this type of trade depends on how high general manager Joe Cronin and the Blazers are on particular draft prospects and whether they think there's a significant enough gap between the available players to make a move up worth it.