I think his point is that money by itself is not enough. You need a strong farm system to withstand the grind of an entire season. Remember that even though the Sox went on their short contract binge last season, if it were not for the contributions of Carp (minor trade), Workman, Bogaerts, Iglesias (who helped tremendously then brought Peavy), Britton et al, the Sox don't win the WS.
If a couple of important Yankee old timers get injured (which is very very likely), who replaces them? And if they need to acquire an impact player like Peavy at the deadline, who do they trade for him? Being able to absorb bad contracts doesn't give you the same mileage it used to.