Thanks for your responses guys. Yeah his entire upper body is shit lol.
He can military press 95x8 and do one chin-up with 75 pounds assistance. I know that seems really, really shitty but keep in mind he is significantly overweight.
The only thing that concerned me is the starting strength program doesn't include any other upper body exercises then pull-ups, bench, and military press. This doesn't seem to be enough for my friend. I'll start including more upper body exercises.
Next time we bench I'm really gunna make sure he's keeping his upper back tight. It's probably a technical aspect because when he benches it just doesn't look quite right. I'll actually upload a video of him benching as soon as I can. That should help explain things better.
It's just strange because his lower body is developing at such an incredible rate. I want to see how fast I can get his deadlift to 500 pounds lol. I think I could do it within the next 6 months.