1938: Winston Churchill smoked from an early age, but the image of him chomping on a long cigar, two fingers raised in a V-sign, dated from the Second World War. These Tremendous Years 1919–1938, published by the Daily Express in 1938, associated cigars instead with F.E. Smith, the Earl of Birkenhead. Churchill, according to the Daily Express book, was noted not for his cigars but for his hats.
Source: These Tremendous Years 1919–1938 (1938), p. 140