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1905–1907; 2019 · South Bend (boundary)
The mayor's memoir is Pete Buttigieg's Shortest Way Home (Liveright, 12 February 2019, ISBN 978-1-63149-436-9), written by the sitting and then former Mayor of South Bend (in office 2012–2020) — the public official as memoirist at full strength: a first-person account of governing the county seat, published while its author held and left office. The newspaper years belong to Ring Lardner, who worked at the South Bend Times from 1905 to 1907 — society reporter and sports editor in the staff records' telling — and discovered baseball writing there before the national career. Both entries are South Bend entries. Osceola has no mayor — it is an incorporated town with a town council, not a mayoralty — and no official's memoir and no national name's staff years appear for the town or Penn Township in the record reached; Samuel Ireland's "Memories," already banked, is a settler's memoir, not an official's, and is not promoted into this row.
Sources: publisher records for Shortest Way Home; Encyclopedia.com, Library of Michigan, and AMSAW records for Lardner's Times years.