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He can do it once per assignment phase. In general, things that happen "at the start of" can only happen once each time that happens.If there are any fierce minions, then there will be a second assignment phase, and his ability will trigger again. When that happens, he can choose the same or a different companion.
Larry50001 is the new Larry5000. We still have a separate place for you to ask questions as opposed to starting multiple separate threads.-wtk
Not at all, welcome back! It's just easier to keep things all in one place and organized, especially if some new player comes through and has many of the same questions you have. Remember you can always check into http://www.gempukku.com/gemp-lotr/ and ask questions in the game hall, too.