[2][3] After being educated at Lancaster Royal Grammar School, where his mathematician father was headmaster, Shackleton Bailey read first Classics and then Oriental Studies at Gonville and Caius College, Cambridge, before spending the years of the Second World War at Bletchley Park, the home of the British code-breaking efforts.
In 1955 he migrated to Jesus College, Cambridge, where, as Director of Studies in Classics, he began publishing the long series of books and articles on Latin authors that would occupy the rest of his life.
This time, his move was reputedly because Sir Denys Page, Master of Jesus, refused to allow Shack (as he was commonly known) to have a cat-flap installed in his ancient oak door.
In retirement he prepared many editions for the Loeb Classical Library published by Harvard University Press, including those of Martial, Valerius Maximus, Statius, and the correspondence of Cicero.
[2] He was extremely fond of cats (the first volume of his seven-volume Cambridge University Press edition of the Letters of Cicero is dedicated to Donum, a feline present from Frances Lloyd-Jones) and of classical music.