This sounds hauntingly like a book I read about 25 years ago called "The Magic Feather" about a child who got shunted into special education... and unfortunately thousands of parents could have written a similar story.
YOu have few choices and most of them are of the Catch-22 variety. Be sure to consider ones that might not have occurred to you, like homeschooling for a year to get those skills he didn't learn and to get some maturity and confidence.
I think in your position I would make a list of the choices and discuss it with your kiddo, and write down the good & bad of each. INclude the option of simply going to the school and telling them you refuse "special ed" services. If he is not going to learn, he might as well not learn in the regular classroom.
I would also aggressively look for ways to keep school from being the dominant force in his life. Robert Brooks talks about developing "islands of competency" -- making sure your child has somethign that *he* is good at, knows about, and continues to grow & leanr about. He jokingly talked about teaching the child to use a screwdriver and to tighten the screws in the chairs at the house... and loosening them if need be to make sure there was a need... and then spreading that to noticing other things that needed ot be taken care of and getting those skills. (And I have learned not to underestimate this from my sister, who suggested to a sully, lazy worker on our swimming pool crew that while we were doing a fast-paced part of the job that he couldn't keep up with, he could go back to the truck and prepare it to load things back on... and then she praised his efforts. Danged if this guy didn't start looking forward to that part and getting a more positive attitude and looking for things he *could* do well instead of leaning on the scrub brush and scowling. The ego is an amazing thing!)
Now, that's all based on the idea that the school is utterly dysfunctional -- it just might not be **that** bad. Just don't count on it.
What do their educational evaluations say about him?
When students were mainstreamed where I taught, they tended to get lost in the shuffle. SInce they went from my class of 7-10 students, to classes of 20 or 30, they tended to sit in the back and disappear; they didn't turn in homework or classwork, both because they struggled with the language demands (much more words, words, words and less drama and pictures and songs -- no grabbing your buddy and acting out "impressment" into the Navy) and because nobody noticed if you didn't hand it in (sometimes teachers didn't want to "make them feel bad" because they were "those special ed kids").
If I were a mom in that situation, I'd try to make a positive impression from day one -- call the secretary and make an appointment to see some of those teachers in the regular classes that busy week before school. Maybe ask the secretary if chocolate would be good currency :-) Then don't take too much of her time, but let her know you really want your child to succeed and *learn,* but that you know he struggles with some things, and ask what kinds of homework she assigns and for suggestions for how you can help your child learn to do this harder work, and for suggestions for how to keep up with the assignments so he doesn't come home and say "don't got no homework" until you get the report card.
I'd be totally honest with the kiddo about how it could be really hard to pass the classes, but that your goal is that he be learning and trying his best, and that he can tell you if things aren't going well and you'll work together on it, and you aren't going to be horribly disappointed in him -- that your biggest disappointment would be if he didn't trust you enough to tell him if things weren't going well. Then I'd find a way to make myself not get disppointed, frustrated, etc ... or at least not to let it show :-)... because 'way more important than ANY of this school stuff is having a kiddo who can come talk to you about stuff. (Now, I don't know your relationship with him so I don't really know how much this applies -- I do know sometimes it just doesn't matter, some young & old teens will go to *anybody* before they go to Mom, somethign about the biology... in which case you have to try & find an ally who Is NOt Mom who can serve the same function.)
Okay, I"ve matched you for rambling :-) Of course the advice is worth at least what you paid for it... and I'm not a mom (though I've been that Ally Who Is Not Mom a few times :-)), just somebody who's worked with teens & adults on this stuff.
Sue J, webmastress
www.resourceroom.net