Mayor Cummerbund is generated with a leather cloak, high boots and leather gloves. He also has a 33% chance of having a rustproof cutlass (scimitar), a 33% chance of having a fireproof leather jacket, and a 66% chance of having a fireproof buckler (small shield).
"Cummerbund" is mentioned in the in-game encyclopedia entry for "Dread Pirate Roberts" as the given name of one of several pirates who formerly held the title of "Dread Pirate Roberts" in the book/film The Princess Bride, so it is likely that the "Mayor Cummerbund" the player meets represents the same individual.
It is not clear if the quest is meant to take place before, after, or during Cummerbund's tenure as Dread Pirate Roberts, but in light of the tone of the encyclopedia entry chosen for him, it seems likely that it takes place after he has retired from full-time piracy to become leader of the pirate community on Tortuga.
Mine was a name that struck fear into men
And regret into plenty of lasses
Oh, how I wish I could take back those days
As I stare at these empty beer-glasses
I think of the times past when I had it all
I toyed with men's wives and their daughters
And in my pursuit of this ill-gotten wealth
I stabbed and I slashed and I slaughtered.
And for what?
The men that I've fought
Are matched by the number of women I've bought
And for what?
I've killed and I've shot
And reddened the cold tears of children with blood
And If I could go back and make my amends
I'd make all those mistakes again
I'd kill every last one of those bastards, my friend
Reference: Chris's Pirate Patch