Life as an Australian Army combat engineer, dismantling bombs and booby traps during the Vietnam War, has left him with just three fingers and a thumb between both hands.
But, thanks to daily assistance from his wife Pauline (55), the handicap did not stop the 60-year-old from sailing around the world on their yacht, the Rum Doodle 2.
The Hobart-based retired couple achieved the feat between 1985 and 1992, and recently decided to hit the open seas again, at this stage planning to sail around New Zealand, Hawaii, Alaska and the west coast of North and South America.
Mrs Theodore said they had been itching to do the trip because neither of them had been to New Zealand before, and Mr Theodore loved sailing so much "he had salt in his veins".
Rum Doodle 2 - a 20m, five-berth US-built ultralight displacement sail boat with an added 200hp Volvo engine - was originally designed to race in the Trans-Pacific Yacht Race from the United States' west coast to Hawaii.
The boat can be sailed by two people, and it is quick. It sailed the 1770km from Hobart to Dunedin in six days.
During long or difficult voyages, the couple had crew members to help sail the large boat - mainly close family members.
They had "divested" themselves of everything on shore and bought the yacht to acquire the ultimate freedom in life.
To explain the appeal of sailing, Mr Theodore hooks his only thumb over one shoulder and points to a memorial board on the cabin wall behind him. It displays the medals he received during combat in Vietnam, along with the phrase: "For those who have fought for it, freedom holds a flavour the protected will never know."
He says people do not realise the value of freedom and life until they almost die.
Mrs Theodore said when they left Hobart, they were not planning to travel around the world again.
But now that they were in Dunedin, they could not rule it out. That was the beauty of their lifestyle, she said.
"The decision will be made when we reach Cape Horn."
