I think Wilshire is pretty far ahead of him, but then I don't think they're ever going to be playing the same role. Henderson is a foil, Wilshire is the one that conducts. I think Cleverley wants to be the most involved one as well to be honest. Neither Wilshire or Henderson are typically "English" of the last 10-15 years. Every English midfielder wants to be at the centre of things, but few of them genuinely manage to control it like Wilshire does. Just as few are happy to provide the platform like Henderson or Carrick does. I don't mean "the dirty work", that shit that people suck Scott Parker off for as if they're still serving a lifetime sentence for failing to recognise Claude "shite Didi" Makelele as the greatest footballer ever to kick the ball. I mean the one touch passes and the plethora of selfless off the ball running he does.
... Course that often looks like nothing, and it often is, because at 21 Henderson's biggest crime is basically that he only really plays well when the team is functioning. If we're doing well, he's usually there with a bit of swagger. If we're not he looks invisible because, hey-ho, most of his contributions are. The thing that got Carrick bit of praise was that in his mid-20s at Spurs you saw a few more expansive passes, or dribbles like when he almost scored at Highbury for Spurs (youtube it). The sort of stuff we saw from Henderson against Fulham but is intermittent that you've forgotten the previous example from months ago when he comes up with a new one.
There's the other thing as well for me personally. I don't really think he knows exactly his role. He knows that he's there to be a foil for Charlie Adam or Steven Gerrard, and he makes good off the ball runs to give them space... but the truly telling bits of play, like making sure he gets up in support of his front man. That's not there. That's not entirely his fault. He's moved about a fair bit for one, but he's also playing a really weird role because of Charlie Adam. I'm not having a go at Adam 'cos I rate him and this is what he is and what we knew we were getting. He's the one that likes to do the attacking stuff in midfield, but he's not the one that's getting into the box and backing up the play. You kind of need Henderson to be the one doing a lot of the doggy work and being quite passive, but also the one that's gambling when the ball gets up there to Carroll, which he doesn't. He doesn't read those situations at all really. We sort of need him to play like Carrick did, but make Frank Lampard gambles into the box. Increasingly so with Gerrard getting older.
That's one of the reasons I prefer Shelvey personally. I think he has a lot more idea of what he's meant to be doing in his role, when he gets the chance to play. Plus there's the general swagger he has about him that Henderson does't. Henderson is just like so many players we've had over the last X years. It's like no one has told him he could actually be really bloody good. Shelvey seems to believe he's the best player on the pitch even when he's playing Napoli or United away.