what if he drops out because he hates the people at the T14? what if China invades and we're all sent to concentration camps based on where we went to grad school? i don't think that it's so incredibly wild to assume that the OP may have a better shot at finishing better in his class at a T40 than at a T14 given the level of students. that being said, you failed to address my main point which is that there are MANY more things to consider than just academic prestige: scholarship money, location, family ties, to name a few. without more info regarding the schools he's considering, it's hard to say either way. if OP were talking about W&L (T40) and UVA (T14), then it's pretty much a no brainer. however, if we're talking about University of Arizona (T40) and NYU (T14), then there's a LOT more to consider.
again, i am aware of the consensus on this board that the T14 is sacred and should not be passed up NO MATTER WHAT, but i think OP COULD be in one of those unique situations where he may need to consider it.