J.C.Squire, Sir John Squire, was an essayist, poet, and editor who for a time was a powerful figure in the London literary scene. His work became unfashionable and I believe he fell on hard times, living on the streets for a while (though my memory could be at fault here.)
IF or HISTORY REWRITTEN. The Viking Press. New York, 1931.
IF IT HAPPENED OTHERWISE: LAPSES INTO IMAGINARY HISTORY. Longmans, London, 1932 (reissue)
Each volume contains eleven pieces. Guedella on if the Moors had won, Chesterton on a marriage between Don John of Austria and Mary Queen of Scots, Maurois on if Louis XVI had been firm, Belloc on if Louis XVI's escape had succeeded, Fisher on Napoleon's escape to America, Nicolson on Byron as King of Greece, Churchill on if Lee had not won at Gettysburg, Waldman on if Booth had missed Lincoln, Ludwig on the survival of Wilhelm II's father, and Squire on if Bacon had written Shakespeare are common to both. In addition the American version has Van Loon on if the Dutch had kept New Amsterdam while the British edition has Knox on a successful General Strike.
It's been reprinted several times, I seem to remember some later versions have Trevelyan on Napoleon's victory at Waterloo.It's reasonably easy to obtain and some of the articles have been reprinted elsewhere (though I forget the details.) The essays vary greatly in interest but it's well worth the trouble of hunting it out.