It can be more satisfying to help an up-and-coming program reach heights they haven't in years, rather than be a cog on a team that is already great and has won titles. That is a risk, because you might not reach the team goal or your individual goals.
But there is a risk with going to a top team also, you might not become a team leader, you might not be that special to them. Whether the up-and-coming team reaches their goals or not, your leadership skills will increase greatly.
Almost all schools have great academics, don't listen to the people who insult them. But do check out which college fits your academic style the best.