See, this is something that I as a non-US citizen just don't get. Jackets with letters on them? 'Lettering' in something? Does M really stand for mathlete?

All that cross-culture confusion aside this was a simple tale of a teenaged boy trying to be normal. His life is anything but so it is easy to see why this is so important to him. Nice of Dean to recognise the need and accept it rather than ridiculing him over it. But then Dean does idolise Sam, always has. A nicely done snippet of pre-series.