Ok, this one's really obscure but I'd wondered what "squires" meant in the song for years.

Happy Birthday!

Sir Richard Anderson Squires

was born 1/18/1880 in Harbour Grace, Nfd.
(d.3/26/1940),

He was prime minister of Newfoundland (1919-23; 1928-32) Began as Peoples Party and then gained a reputation for being opportunistic, extravagant, and corrupt but whose promotion of education and industrial development laid the foundation for the Newfoundland Liberal Party's emergence. [Eny.Brit.] No wonder "Tory" ran him down.

                          There's men of all ages and boys in the bargain,
                          There's old Billy Cave and there's young Raymond Brown,
                          There's a red rantin' Tory out here in the dory,
                          A-runnin' down Squires on the squid-jiggin' ground.
  
                  "The Squid-Jiggin' Ground" My Newfoundland : stories/poems/songs
                  by A.R. Scammell. 1966, etc.

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