I found a few references to the same problem:
iTunes 9.1 - Smart Playlist Sort Order Still Wonky
iTunes 9 + Smart Playlist + Live Updating + iPhone = FAIL
Preserving smart playlist order on iPhone
and then this "fix" from Apple
None of those solutions worked for me. What did seem to work was to set iTunes to sync all copies of all podcasts (the default was to sync only unplayed).

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