As many of you know, researching history is my "thing".
Thanks for the extra photos which show the London date stamp 'S' for 1913. That is the date engraved on the cuff, not 1915.
So, here is how I read it, with some research and imagination.
Hugh was the owner of the Printers, his staff gave him the cuffs as a retirement present due to ill health in 1913.
He was a wealth man, who probably owned a few gold watches and didn't need another.
He had more than one house or premises at the time of his death in 1915, Fetter Lane was one of them.
Cuffs because he or the printers was in FETTER Lane.
Pieman = he liked his pies too much (died age 49) or gave his staff pies for lunch.
Pirates = crew = staff
As someone said "you had to be there". Sounds like multiple in-jokes.
If you jump on Ancestry.com armed with the name and year of death you will find his Eton University education, Printer to the Queen/King, Freedom of the City of London, partner of Eyre & Spottiswoode, his father is buried in Westminster Abbey, p120 Burke's Peerage and Baronetage 69 Edition, p667 Who Was Who 1897-1916,
Some more distant relatives = "Captain John's father, William Spotswood, a 'Revolutionary' publisher in Philadelphia"http://freepages.genealogy.rootsweb.ancestry.com/~coolumkids/
Have fun, without the story it's just a silver handcuff