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"He loved life. He loved Anne."
– Carter Winston (impostor), 2269 ("The Survivor")
"...a living legend, the foremost space trader of our time."
– James T. Kirk, 2269 ("The Survivor")

Carter Winston was considered the foremost Human trader of the middle 23rd century. He became a living legend by acquiring a dozen fortunes, only to use his wealth time and again to assist Federation colonies in times of need or disaster. On a personal level, he was described by his fiance as the gentlest, most thoughtful man she had ever known, and by his Vendorian caretaker as someone who loved life.

In 2259, the colony of Cerberus experienced a crop failure, and the entire population (including Leonard McCoy's daughter Joanna) was in danger of starvation. Winston saved the people of Cerberus by using his personal fortune to bring in enough food and goods to carry the colony through the crisis.

Winston went missing circa 2264, when he was engaged to Starfleet officer Anne Nored. Winston's one-man ship was disabled in a meteor storm and crashed on the planet Vendor. Winston lived under the care of a Vendorian until 2265, often speaking of his love for Nored before succumbing to his injuries.

The truth behind Winston's disappearance was not discovered until 2269, when Winston was seemingly discovered alive and adrift in his ship near the Romulan Neutral Zone by the USS Enterprise. The vessel's occupant was, in fact, the Vendorian shapeshifter who had cared for the real Winston on Vendor, now working as a Romulan spy. His strong feelings for Nored were absorbed and thus shared by his impersonator. (TAS: "The Survivor")

Carter Winston makes a brief but significant appearance in the final chapters of the TOS novel The Final Reflection, in which he assists in the brokerage of a deal with the Klingon Empire for advanced warp technology.
According to The Face of the Unknown, prior to his disappearance, he and Anne assisted in relief efforts on Pangea (β).

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