I know the world will freeze at the end of the World Series, but during the rounds in-between, can players in the last year of their contract be offered an extension? Or does that window end when the season ends?

I've had older players refuse to re-sign.   But I've signed players during the playoffs a bunch of times.

So the older players would have re-signed during the season, but decided during the playoffs that they did not want to re-sign?

That's not what he said but yes, you can sign players in last year of contract during the playoffs.

Posted by swirldude on 12/29/2010 5:59:00 PM (view original):
So the older players would have re-signed during the season, but decided during the playoffs that they did not want to re-sign?

I really can't answer that with 100% certainty because I seldom even bother checking to see who'll re-sign until the playoffs.   The current system doesn't penalize you for waiting until the last minute.  However, because of this, I doubt a player's decision to re-sign changes in the playoffs.  His demands don't.   In all likelihood, the old guys were just intent on retiring.