free weight, of course. i never believed in machine especially when it comes to bench press. i was 6ft 175lb when i was 9th grade. there were plenty of 9th graders who did 225lb 5 times in my high school. i lived in south. we were country strong. everybody was trying out for football.
you don't have to believe me, but my best max was 375. i was 24.
I don't doubt that you can train up to 375 or more. I don't believe an unconditioned person can do 185x5 after only 2 months of lifting. At least from my experience. But I do agree that 185x3 for a 6 foot athlete should be easily doable. A lot of younger players avoid heavy lifting and bulking because it would affect their speed. I'm sure he'll be able to put on some muscle in the next couple of years.