The Portland Trail Blazers were expected to trade Anfernee Simons, but no one saw their decision to swap him for Jrue Holiday coming. Before shipping him to the Boston Celtics, the most frequently rumored landing spot was the Orlando Magic.
It was a perfect fit, as Orlando desperately needed Simons' combo guard skill set. He would've provided valuable floor spacing for a team that ranked dead last in three-point shooting (31.8%) by a wide margin last season. He also would've relieved some of the playmaking burden from star forwards Paolo Banchero and Franz Wagner, offering them a secondary offensive initiator.
Of course, the Magic ultimately decided to take their roster in another direction, addressing their shooting woes by sending a massive haul to the Memphis Grizzlies in exchange for Desmond Bane. That blockbuster deal took a Blazers-Magic trade off the table. It's unfortunate, as the Blazers could've potentially stolen an underrated up-and-coming piece: Anthony Black.
Blazers missed their chance to steal Anthony Black from the Magic
Black wasn't directly linked to Portland by any means, but he was included in the majority of proposals that were floated during the seemingly never-ending Simons-Magic rumors. That would've been an excellent addition for Portland to add to their young core, especially given their current question marks in the backcourt.
Now in Year 3, Black has quietly had a breakout season in Orlando, averaging 15.3 points, 4.1 rebounds, 3.8 assists, and 1.3 steals on 45/34/72 shooting splits. He's taken a significant step forward with a red-hot December in which he averaged 18.9 points per game, including a stretch where he had 20+ points in six of seven games.
The most impressive aspect of his breakout is that Black is a two-way guard who isn't known for his scoring. Undersized, offensive-minded guards are quickly losing value around the league. Black, a versatile 6-foot-7 guard, is the antithesis of this.
This league trend also suggests that Portland was wise to move on from Simons. Still, time will tell if Portland's decision to take on Holiday actually turns out to be in their favor. Holiday played well for the Blazers early on, but unfortunately, we only saw that for 12 games before he suffered a right calf strain. He certainly doesn't fit their rebuilding timeline as well as the 21-year-old Black, whose careers are trending in opposite directions.
The Blazers still need to find their long-term solution at the point guard position, and having Black's combo guard skill set as an option would've made them feel much more comfortable about their future outlook in the backcourt.