One of three very similar Raeburn portraits of Hamilton (see Originals and Copies), although the Bailey version differs more than the other two. The original has remained at Lennoxlove, the Hamilton family seat in Scotland. The Bailey version and the other recorded version were probably painted at the same time as the original, likely 1785, for other family homes.
A label on the back of the canvas indicates that the Bailey version was in the Lord Rossmore collection. It is recorded as being in the hands of Leggatt Bros sometime in the early 20th century and probably passed direct from here into the Bailey collection. The other version was sold at the Hamilton Palace sale, and was in the hands of Christie’s in 1919 where it was bought by a Mr Watson for 6300 pounds.