Captain Thomas "Tommie" Samuel Henning's life evolved around the sea and boats from a young boy. His grandfather and father were both Master Mariners and among the first schooner builder and sailors in the Cayman Islands. Even a permanent disability of his leg due to contracting rheumatic fever at the age of 19 did not stop his love of the sea. At the age of 27 he answered the call of the sea and he left Grand Cayman to sail with Suwannee Steamship Company as an Ordinary Seaman and soon advanced to Chief Mate. In 1949, he joined the Eastern Steamship Company till he transferred to the West India Line in 1957 as Captain. Where he remained until his retirement in 1978. During that time he captained the ship that bought equipment to Cayman to build the first surfaced road; which stretched from West Bay to Bodden Town. While he retired in 1978 the sea soon called again and he joined Herbart Humphrey Jr, as Navigator, on the Pelorus Jack and The Beacon the same year until 1988. Captain Henning was reputed to be a precise navigator and did not sail without his sextant. Only using modern navigation equipment as a secondary tool. His love of sea was only surpassed by his love of God; his wife Lida Venell Jackson; their Children, Robert and Nellie Joy and granddaughter Andrea.

Captain Thomas "Tommie" Samuel Henning's life evolved around the sea and boats from a young boy. His grandfather and father were both Master Mariners and among the first schooner builder and sailors in the Cayman Islands. Even a permanent disability of his leg due to contracting rheumatic fever at the age of 19 did not stop his love of the sea. At the age of 27 he answered the call of the sea and he left Grand Cayman to sail with Suwannee Steamship Company as an Ordinary Seaman and soon advanced to Chief Mate. In 1949, he joined the Eastern Steamship Company till he transferred to the West India Line in 1957 as Captain. Where he remained until his retirement in 1978. During that time he captained the ship that bought equipment to Cayman to build the first surfaced road; which stretched from West Bay to Bodden Town. While he retired in 1978 the sea soon called again and he joined Herbart Humphrey Jr, as Navigator, on the Pelorus Jack and The Beacon the same year until 1988. Captain Henning was reputed to be a precise navigator and did not sail without his sextant. Only using modern navigation equipment as a secondary tool. His love of sea was only surpassed by his love of God; his wife Lida Venell Jackson; their Children, Robert and Nellie Joy and granddaughter Andrea.