Many poor transit investments have arisen from a too-small group of fortunate people assuming that everyone shares their tastes and priorities. They forget that to be elite is to be a minority, and it makes no business sense to design transit around elite tastes if what you really want are lots and lots of riders.
And good transit to airports or baseball stadiums might be good projects (though not if these destinations are the primary purpose, usually), but transit decisions are driven by people who imagine riding transit is something they would do occasionally in certain circumstances, instead of by/for people who use it every day.