I've seen it used around the 1960 time frame. There is a 1960 Juice Glass that features this same Pirate, along with a salute to the 1960 Championship.
They also had a more cartoonish Pirate Mascot at that time. I would say this Mascot is the less "common" of the two. It was probably used from the late '50s through early '60s.
Hope this helps.
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