1. With two lottery picks, Blazers can swing for upside
Not only did the Blazers lose the "coin flip" to the Hornets to determine draft position, but they also seemingly lost when the Golden State Warriors received the No. 14 spot, giving the No. 13 spot to the Sacramento Kings. Both teams finished with a 46-36 record.
The Blazers obtained the Warriors pick from the Jrue Holiday trade with the Boston Celtics, in which they also sent over Malcolm Brogdon, Robert Williams, and a 2029 Celtics unprotected first-round pick. One could even argue that it wasn't that significant for the Blazers that the Warriors received the 14th-best lottery odds as opposed to the 13th because the pick was top-four protected. The Warriors winning the coin flip would've resulted in them having a 3.8 percent chance at a top-four pick instead of the 3.4 percent chance they had.
The Blazers' most significant need to address this offseason is shooting, yet many top draft prospects aren't great shooters at this stage in their careers. The elite shooters that will likely go in the lottery include French wing Zaccharie Risacher, first-team All-American Dalton Knecht, and Kentucky guards Rob Dillingham and Reed Sheppard.
Unfortunately for Portland, Risacher likely won't be available by the time they are on the clock, and neither Kentucky prospect seems to make sense in terms of fit, as both are undersized guards. If the Blazers went the Knecht route, they'd be sacrificing defense and upside, as he is already 23.
After finishing dead last in the Western Conference, the Blazers shouldn't rush into trying to contend anytime soon, regardless of Anferenee Simons' recently expressed desire to win now. With two lottery picks in a draft and many unknowns, Portland can afford to take two high-upside swings on prospects.
Multiple prospects already contribute to winning but aren't efficient shooters, which is Portland's biggest weakness. The Blazers can afford to select players that fit this mold and bet on them becoming above-average shooters, making them NBA-level starters if they reach their potential.
There is some good that comes with finishing with the worst record in the Western Conference after trading away arguably your franchise's best player ever, and that is the fact that expectations are low for years to come. The Portland front office can take advantage of this low bar by taking flyers on prospects that may need more years to develop, especially now that they officially have two lottery picks.