[beorn]

In an online league, I re-signed a 39 year old reliever to a two year deal right at the end of the regular season. He then retired at the end of the playoffs.

This is not a big deal, and not unheard of, although not the usual way things would go.

It would be a nice touch if older players very late in the season accepted offers, but responded to a good offer in the general vein, "I like your offer but have not yet decided whether to continue my playing career next year." Then send either a retirement or acceptance at the end of the World Series.