It sounds like he received his old role PM. Originally, Dana Cardinal was the mayor and Pamela was the gossip but Retro decided to switch them so that things were more lore consistent with the beginning of the podcast. Mike must have gotten Pamela's old PM which was for the gossip. So he didn't know that I (Dana) was a gossip but he, reasonably, assumed that there was still a gossip in the game.
That's my bet.
Edit: Also, putting that ramification together, I was so close to getting the override power
One of my few dreams.