Mayor of Michel Delving

The office of Mayor is implied to have been well established by the end of the Third Age, but we have very little definitive dating evidence around the role (and indeed very little detail of any kind about the Mayoralty's history). The earliest definite date we have is III 3013 (Shire-reckoning 1413), the most recent date that Will Whitfoot must have been elected as Mayor, but surely the office dated back to a considerably earlier time.

It is implied (though not stated outright) that the title originated as the Mayor of the town of Michel Delving, and was only later expanded to cover the Shire as a whole. That in turn suggests that the position was created rather early in the Shire's history. So, in principle, the Mayoralty might date back to the earliest days of the Shire, or at the very least to a period several centuries before the War of the Ring.

We have no way of knowing when Will Whitfoot's time as Mayor began, but the latest this can have been was in III 3013, the date of the last mayoral election at a Free Fair before the War of the Ring, and thus the last point he could have been elected. As a popular and distinguished old Hobbit, though, it's implied that Old Will had held the position for rather longer than the fourteen years we can definitively establish.

Tolman Cotton (eldest son of Farmer Cotton) had served as Sam's Deputy at one time, so he might be considered a plausible candidate as Sam's successor, if not for the fact that both these Hobbits had been born in the same year (III 2980). At the age of ninety-six, then, Tolman would have been a little past his prime, and it seems more likely that a member of the next generation of Shire-hobbits would have been elected to the Mayoralty.