Should teams in Cleveland's or KC's position even try to trade elite pitchers for young pitching prospects, even in masses as we have tried to do, or are we just kidding ourselves and should we instead try to accumulate hitters (who can more reliably be evaluated and also expected to get to the majors)?

Rob Neyer directs our attention to a public Google Doc compilation of 21 years of Baseball America top 100 lists (pretty good work from anonymous, in and of itself) and draws the sad old TINSTAAPP lesson. He then goes on to bemoan the recent Greinke to the Brewers trade. Given that the Tribe has itself been known to trade a Cy Young award winner or two (nearly three) in recent years, his criticism of KC can be seen by reflection as also a criticism of Cleveland.

Should teams that are predictably going to be mediocre at best while rebuilding keep or trade a great pitcher for more though younger pitching prospects? And if the team decides to trade that pitcher, should the team try for pitching or hitting prospects back in return?

Attempting to keep a good pitcher on a terrible team is unrealistic and a waste of money, we can all probably agree. "Cashing in" before the pitcher reaches free agency seems to be the only way to go, pragmatically speaking, and not just the right way. Neyer, pointing to TINSTAAPP, seems to be saying by way of warning, "just don't think you are getting any real pitching back in return" if you trade for pitching back.