"He was a brilliant banker, but never developed a taste for tailor-made suits or fashionable neckware," remembers a former colleague.
Mr Redwood entered the City with a first in history and joined Robert Fleming, the vast privately-owned investment bank with strong Scottish connections and a patrician approach to its employees.
He used his prestigious intellect to analyse companies, searching for bargains to buy for his investors. He quickly shone and in 1977 moved to Rothschild Asset Management, one of the most pukka names in the City and sometime employer of many Tory ministers including Norman Lamont and Lord Wakenham.
Colleagues regarded him as one of the brightest talents in the Chetwin House office. But in the Mess - Rothschild's sumptuous directors dining room - his ambition and conscientiousness made him too purposeful to be clubbable.
He left Rothschild when Baroness Thatcher appointed him to her policy unit. Two years later, out on the street after leaving No 10, he turned back to the bank and met with Sir Michael Richardson, head of Rothschild.
Sir Michael listened to Redwood's argument that the privatisations of British Gas and Rolls Royce, would be repeated across the globe.
He made the bold decision to take him out of the sleepy confines of fund management and move him to the tough bear-pit of corporate finance, selling Rothschild's services abroad through NM Rothschild.
"When he first arrived we all thought he was completely bonkers," remembers another former colleague, "but he turned out to be right about privatisations."
Mr Redwood travelled the world selling Thatcher's gospel and Rothschild services. "It's become one of the most profitable ventures the bank has ever entered into," said one employee.