I’ll have to ask him that too. He’s about seven years younger (but Punahou has all the grades mixed in — and he definitely followed the basketball team, at the time BO was supposedly a big hotshot star of the team).
In 2009 a classmate of Obama’s made a YouTube video of him in the Punahou yearbooks:
http://m.youtube.com/watch?v=ri_TnW6I7O0
and the Punahou School Senior Prom photo:
http://swampland.time.com/2013/05/23/time-exclusive-obamas-1979-prom-photos/
Your BIl is seven years younger?
So when Barry was a senior your BIL was in the 5th or 6th grade?