Bred and owned by Lord Derby, one of the leading patrons of the turf, Fairway was by Phalaris out of Scapa Flow by Chaucer making him a full brother to Pharos who was second in the 1923 Epsom Derby. Fairway won twelve of fifteen starts including: the Coventry Stakes at Ascot, the July Stakes at Newmarket, and the Champagne Stakes at Doncaster as a two year old in 1927. At three, he won the Newmarket Stakes, the Eclipse Stakes at Sandown, the Champion Stakes at Newmarket, and most importantly the St. Leger at Doncaster despite his earlier troubles in the Epsom Derby. Fairway was the 3-1 favourite for the Derby and was quiet in the paddock while being saddled. Unfortunately, as he was being walked on the course before the race, the excited crowd, surrounded the horse, and even plucked hairs from the horse's tail for souvenirs, leaving his tail in 'rags and tatters'. Understandably, Fairway became very upset and covered in sweat. After three false starts, the race was won by Sir Hugo Cunliffe-Owen's Felstead with Fairway finishing thirteenth in a field of nineteen. At four, he continued his racing career winning Newmarket's Burwell Stakes, the Princess of Wales's Stakes, the Champion Stakes and Jockey Gold Cup, as well as the Rous Memorial Stakes at Ascot. He enjoyed a very successful career at stud where he was the Leading Sire in England in 1936, 1939, 1943 and 1944.
In 1937 Munnings was commissioned by Lord Derby to paint Hyperion, the winner of both the Epsom Derby and the St. Leger in 1933. The painting and the present work are discussed in detail in the artist's autobiography: 'The last two horses I painted in Newmarket were Hyperion and Fairway. Hyperion had then been at stud - was it three or four years? I wonder if Hyperion was the smallest horse that won a Derby ... The stud-farm where Hyperion and Fairway dwelt in adjoining boxes, if it were advertised in a journal read by horses might be described as a large two-roomed flat, on the ground-floor, in ideal surroundings. No other two horses were housed better or were in the care of better attendants. Chinery, a heavy man of medium height, full red face, with big arms and thick calves, which always looked as though they were bursting out of their leggings, was Hyperion's groom. Cain (I then called them Cain and Abel), a shorter and more wiry man, with a thinner face and a hooked nose, and of small dimensions, was Fairway's groom." (see Sir A. Munnings, op. cit., p.41).
One can clearly see how Munnings reused this image of Fairway in the background in his painting of Hyperion held by Chinery which was exhibited at the Royal Academy in 1938 (see S. Booth, Sir Alfred Munnings 1878-1959, London, 1978, p.194-95, illustrated). 'Lord Derby did not want my two studies of Hyperion and Fairway. That spring I hung them in my own exhibition at the Leicester Galleries. In 1940 they were in the Gem Room Gallery No. 9 at the Academy. After the exhibition was over and the Army occupied Castle House, I took them, with the bulk of my work, to Exmoor. Both pictures were hung in my sitting room at Withypool, where I saw them every day, and I was as near satisfied with them as I could be'. (see Sir A. Munnings, ibid, pp.45-6).
In a letter from the artist dated 18 December 1950 to the American owner of this painting, Munnings writes: 'quite one of the best paintings I ever did of a horse & one that I'm fond of, also the same can be said of the portrait of Cane (sic) the groom. I'm keeping the photograph for my new book as I write of the painting of these two horses'.