As a practice partner, have your varsity heavywieght work on bottom against him. If he can get up and defend against a 370 pounder on top of him, he should have no problems with 285 pounder.
As for the weight problem, if he is weighing 370 then he probably doesnt get much excercise so the weight will come off realatively fast without altering his diet just from goin to no excercise to 2 hours of intense wrestling practice will make him drop alot of wieght. Just goin to practice, working hard, and maybe cutting out something simple like late night snacks or soda will probably get him down to a weight where he could cut to make 285.
I think he could wrestle at weight by the end of the year because big people cut weight alot faster, they sweat more and burn more calories just by walking around. So even if he can get to around 315 or 320 he could easily cut down to 285 in a few days.