Harry Truman 'Toby' Caldwell

Harry Truman "Toby" Caldwell passed away peacefully on Mar 1, 2022 in the home he built with his own two hands.
He was born on July 13, 1945 in Portsmouth, VA to Frank and Gladys Lawson Caldwell. Frank was working construction at Portsmouth Naval Hospital at the time. Gladys went into labor while dropping off his lunch resulting in Toby being the only one of their 14 children to be born in a hospital. In an odd twist of fate, Tobys only grandson would be born in the same hospital 52 years later.
Toby grew up all around the Southern US including the towns of Rocky Gap, VA, Manteo, NC, and Norfolk, VA. He eventually settled in Monticello, IN where he met the love of his life, Linda Sharp. They were married in June of 1966 and hardly left each others side over the next 56 years. Together, they raised three kids, Kim (husband, Dale Craig), Frank (wife Denise Parker), and Rox.
Toby loved cars and was an exceptionally talented body man working for and owning several shops in Monticello. In the early 1990s he decided to build his own barge and start building sea walls, docks, and boat houses on Lake Freeman. He owned Toby's Body Shop and later owned Toby's Docks and Decks from which he retired twelve years ago. He loved working with his hands, carpentry, and piddling with cars. In retirement he helped Linda with her daycare, teasing and tormenting dozens of children over the years.
His greatest joys along with pro wrestling, the three stooges, and TV westerns were his five grandchildren, Malyssa (husband, Dakota Trial), Parker, Chloe, Gabby, and Josslyn; and his 2 great grandchildren, Owen and Toby. He cherished his family.
He is preceded in death by his parents, brothers Alfred, Junior, Sonny, Jack, Donald, Dee, Joey, Bobby, and Billy sisters Nancy Johnson and Shirley Hintz. He is survived by sisters Mary Causer and Virgie Fraser, as well as his wife, children, grandchildren, great grandchildren, and several nieces and nephews.
Visitation will be held on Monday, March 7, 2022 from 4:00 pm until the time of services celebrating Toby's life at 6:00 pm (EDT) at Springer-Voorhis-Draper Funeral Home of Monticello with Harold Rutledge officiating.
In lieu of flowers, memorial contributions are encouraged to the funeral home to assist Linda with expenses. Envelopes available at the funeral home.
Friends and family are encouraged to share a photo, a memory, or a message of condolence at www.springerfuneralhome.com