That's a very common play nowadays. Our high school runs plays for that pass, regularly, and more often than not, gets good looks out of it. I would say Trey is pretty decent at it, actually. He had a couple errant passes from that general type of play last night, but I don't think any of them resulted in turnovers? But he also found CJ for a big three during our run, and connected on a couple that easily could have resulted in positive plays.
It works very well against teams that play good helpside defense. The rotations for a baseline drive often leave shooters open on the weak side of the court. As the defense rotates to stop the ball, and then dives to cover the rim. Usually leaves the weak side very vulnerable.
I would say when Trey fails to execute on this play its not because he's dumb. Its because he's not really as skilled a basketball player as most assume he is.