I believe it could since HT would be the last card played (and it was by the opponent). Never mind, Gabe is correct since HT is not played in the current battle.
As for the second question, if we assume Treachery has not been triggered, Two Bears would actually shuffle HT (assuming all 7 evil brigades are not in play besides HT) since you choose all targets for Two Bears and then carry out the shuffle. If all 7 brigades are in play and you shuffle one of each, (including the Herod w/ HT), then HT would follow the Herod.