How do you ensure that with a free agent you don't sign, a trade you don't make or a player you don't draft?
What if we decided to skip over drafting/trading for one of these pitchers we have down on the farm now. Instead we grabbed a positional player to begin with - then the pitcher skipped out on beats us in a playoff series. Do you feel better that way?
What if you lose that playoff series to said pitcher, but you narrowly made it there to begin with? A huge reason being the positional player you received in compensation for that pitcher?
If you want to play this game - it's a never ending circle.
Bottom line, it's never a bad thing to have an influx of talent in any given area and you make moves to better your team. The whole point is that the other team is trying to better themselves as well. So, if you two meet in the playoffs - large in part to the players you've dealt to each other. What a smashing success of a trade that was for everyone.