I've watched Ospreay his entire run in NJPW all the way into AEW.
He's a fantastic wrestler but I've never been into his character work. There were quite a few times in his career (his BoSJ wins, those matches with Shingo, the NEVER belt, move up to heavyweight, feud with Okada) that I felt like Will is starting to figure it out and get a clue, but it feels like he just plateaus rather than break into that next level. Some of his AEW promos have been good, but he's the same guy he was coming in well over a year ago at this point.