The frequency at which his opinions were appealed has given rise to many stories, though according to a modern assessment he "seems to have been a man who has suffered unfairly in the public reputation and [his] appointment was one which was unlucky rather than discreditable."

He was the second son of Samuel Trehawke Kekewich of Peamore House, the Member of Parliament for Exeter in 1826 and for South Devon in 1858, by his first wife Agatha Maria Sophia, daughter of John Langston of Sarsden, Oxfordshire.

There was some surprise when on the retirement of Vice-Chancellor Bacon, in November 1886, Kekewich was appointed by Lord Halsbury to fill the vacancy in the Chancery Division of the High Court, and he was knighted early in the following year.

But his quickness of perception and his celerity in decision were apt to impair the accuracy of his judgments, and he failed to keep sufficiently in control a natural tendency to exuberance of speech.

Several of his juniors on the bench were promoted over his head to the Court of Appeal; but by the legal profession his shrewdness, sense of duty, and determination to administer justice with the minimum of delay were fully recognised.

He died after a very short illness on 22 November 1907 at his house in Devonshire Place; there were no arrears in his court, and he had sent, a day or two before his death, his only two reserved judgments to be read by one of his colleagues.