John Miller Bailiff

It is with great sadness that we share the passing of our beloved father, John Miller Bailiff.

John peacefully passed into his eternal rest on Saturday, January 18, 2025, surrounded by his loving family.

Born in Elkton, MD, on July 10, 1940, John was the beloved son of Theodore Roosevelt Bailiff, Sr. and Bessie (Lowe) Bailiff of North East, MD.

John is survived by his children: Laura Bailiff, John Bailiff, Jr., Anthony Chalkley (Tabatha), Danielle Bane (Howie) and Jacob Bailiff.  He was a proud grandfather to William “Teddy” Lewis II, Tara Lewis, Cody Tiley, Tyler Tiley, Nathan Swauger, Michael Chalkley (Lauren), Matthew Chalkley (Cat), Donald Harrell, Gabrielle Chalkley (Tyler Walker), Andrew Chalkley (Emily), Jesse S. Bane (Kyrsten), Megan M. Esposito (Frank), Noah H. Bane (Savannah), and Emma M. Bane (Andrew). John was also a cherished great-grandfather to Jayden and Caylee Althoff, Adrian Ramsey, KiShawn Fitzgerald, Levi Lewis, Amelia Chalkley, Callum Chalkley, Ellis Chalkley, Everett Chalkley, Mason Walker, Kylie Harrell, Levi Harrell, Lily Bane, Levi Bane, Liam Bane, Lucas Esposito, Violet Esposito, Asher Esposito, Saige Esposito, Hazel Esposito, Reagan Bane, Kennedy Bane, and Gracie Rae Bane. His children and grandchildren were the greatest joy of his life.

John is also survived by his brothers: Jake Bailiff (Marilyn) and Ralph Bailiff, both of North East, MD; and his nieces: Tracy, Dawn, Melanie, and Marnie, all of whom he loved very much.

At the young age of 16, John made a pivotal decision to trade his time at North East High School for barber school in DE. This choice led him to Aberdeen, MD, where he honed his craft and became a master in the art of flat tops and fades. With a steady hand and an eye for detail, John turned each haircut into a work of art, providing his clientele with the luxury of a good old-fashioned hot lather straight razor shave. The King’s Chair, which was his home for over 60 years, became a staple in the community and a sanctuary for many.

Throughout his decades-long career, John catered to a diverse clientele, including judges, politicians, local law enforcement, and even members of the Ripken family.  The King’s Chair was not just a barbershop; it was a gathering place where patrons received quality haircuts, engaging lessons in baseball and history, or simply a listening ear and wise advice. John’s warmth, and charm left a lasting impact on all who entered, and he took great pride in making every customer feel like royalty.

In addition to his parents, John was preceded in death by his brothers: George Bailiff and Theodore Bailiff, Jr.

John’s legacy will live on through the many lives he touched, and he will be deeply missed by all who knew him.

Services will be private.

Obituary lovingly written by the family.