The merchant, who was at the caravan's head, was Dylan. John had asked him to follow along after renting the caravans because they needed an authentic merchant for their disguise. Dylan had been grumbling non-stop after John explained what those caravans were going to be used for after seeing players entering them.
He was sure by the end of the days, these caravans would be full of scrapes if they were not fully broken. Any damages inflicted upon the caravans would incur a penalty when it was time for him to return it. John had assured him that the guild would help pay for the penalty.
He grumbled that it was not just about the monetary penalty, his reputation in the faction would suffer as well. John lectured him about the need for one to sacrifice for the good of many. Jack joined in and lectured him about the importance of their current mission. How they would need to win this war if players were still to have their freedom in this country.