But it sure seems to me that purely as a baseball question, you would much rather give a guy a bigger and shorter contract than stretch it out over six or seven or eight years, where everyone finds themselves facing an awkward ending when the player isn’t worth the money anymore and the team has to figure out how to handle it, the player has to deal with the abuse, and so on.

Honestly, in some cases, I’d rather give a guy four years at $100 million than six years at $100 million.

– Joe Posnanski, SI.com.

I enjoy Posnanski’s writing as much as you probably do, but I’m not sure this makes any sense. Why would a team want to lock up a guy for four years for the same amount of money with which they could lock him up for six years? Is the awkwardness he refers to really so intolerable that teams should give up the chance they’ll get two extra years of production from the player for no additional cost?

I think the problem is only perception: Since teams almost always reap most of the returns on a free agent deal in its first couple of years, they (and their fans) should approach the deals that way and consider anything they receive from the player on the back end as gravy. Actually I wrote almost exactly this same thing in June.

The biggest reason I can figure for any awkwardness is that teams are often hesitant to part ways with sunk cost. I realize there are human interactions involved, and maybe it’s too hard a PR hit for a team to just up and cut a former star player it expects won’t give them any more production than some available replacement. But it happens pretty frequently in football (since large parts of contracts aren’t guaranteed) and somehow the NFL soldiers on in spite of any ill-will created by disloyal franchises.