Ozzy (Angus Sampson)
In exchange for protection of the pathway to the fair, the Highwaymen were allowed access to the celebration, including the highly-coveted movie screening. What they ended up with was the death of their two highest ranking members.
If Ozzy had survived the pikes but still lost his second-in-command, Alek, he would be shaken up and possibly want to pull the Highwaymen away from the communities.
No matter how reasonable a guy Ozzy seemed to be, it is completely fair for the Highwaymen to point some blame at the communities they were hired to protect. Almost as soon as the Highwaymen agreed to help protect the communities on the way to the fair, they lost two (or, in this hypothetical situation, one) of their beloved leaders.
Ozzy was a cool guy who could clearly hold his own on the battlefield, so I imagine that he would be a key soldier in the Whisperer War if he could be convinced to stay.