Boston probably gives Iginla the best chance to win a cup in the next few season. The east is relatively weak, and barring a major surprise they should win the division each year during that time. It didn't work out in Pittsburgh, and they are in turmoil right now. The west is such a crapshoot, unless maybe the Kings or Blackhawks want him (which I don't see happening with their depth) he has a smaller chance of getting far in the playoffs.
I suppose the Flyers could be a possibility, but if his main goal is to win a cup it will likely come down to a few teams.
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