Grading the trade for the Blazers
It would likely take a serious offer to get Cronin to even consider trading Simons. Picks are important to a rebuild, but based on the Lillard/Holiday trade, Portland's GM is interested in young, controllable talent.
That's where Anthony Black and Wendell Carter Jr. come in.
Black was picked sixth in the 2023 draft, three spots behind Henderson. His natural position is point guard, which seems redundant with Scoot on the roster, but at 6-foot-7, he brings a drastically different element to the Blazers' backcourt.
Where Henderson is a downhill creator and Sharpe is developing into a go-to scorer, Black is an intelligent and natural connector. He'll keep the offense humming with ball movement and smart decisions.
He proved to be a good pick-and-roll orchestrator in his one season at Arkansas and has a herky-jerky, stop-and-start ability that, combined with his size, allows him to separate on drives to the rim, similar to Shai Gilgeous-Alexander or Luka Doncic.
The main selling point on landing Black, though, is his defensive upside. Instead of rolling with a pair of small guards, the Blazers would swap out the 6-3 Simons for an instinctive 6-7 defender to add to the duo of Henderson and Sharpe.
Carter Jr. can be what Robert Williams III was supposed to be when Portland traded for him in the Holiday deal. Deandre Ayton has struggled with consistency and injury this season, and while Duop Reath has found a nice role off the bench, Carter is simply a much better player.
Across his two full seasons in Orlando, the Duke product has averages of 15.1 points and 9.6 rebounds in 29.8 minutes. He's developed into a respectable threat from deep. Including the 13 games he's played this season, Carter is hitting 34.6 percent from three on nearly 4 attempts per night.
The two first-round picks - one of which comes in 2025, a draft class widely regarded to be loaded with talent - make it 13 first-rounders for the Blazers between 2024 and 2030. Portland would be approaching Oklahoma City Thunder territory with its draft assets.
Meanwhile, Henderson can continue his recent ascent and either move into the starting lineup in Simons' place or remain as the Blazers' sixth man behind Malcolm Brogdon. Sharpe can get more time on the ball as a scorer and shot-creator. Black will get a longer leash to develop in Portland than he would in Orlando, and Carter Jr. can add more size and skill to Portland's frontcourt.
Losing Ant would certainly be a blow, but he's the Trail Blazers' most valuable asset outside of Henderson and Sharpe. If Cronin is willing to take another step back with the future in mind, this deal would at least be worth an extensive conversation within Portland's front office.
Blazers trade grade: B/B+