I have one of the 1788 versions of this token, with the same obverse but a pineapple reverse. The "pineapple pennies" are quite popular here in Australia, due tot he tropical theme and the 1788 date.
The symbolism of the obverse is interesting: we have a negro-head, crowned with the ostrich-feather coronet and the motto "I serve". What does all this mean?
First, you need to know that the ostrich-feather crown is the badge of the Prince of Wales. Likewise, the "I serve" motto is derived from the German motto of the Principality of Wales, "Ich Dien". There thus seems to be some derogatory symbolism towards the Prince of Wales on this coin (comparing him to a negro slave). What could have caused such offence?
In 1788, the Regency Crisis hit the British government. "Mad king" George III had slipped fully into insanity, to the extent it was obvious to everyone he was not fit and competent to rule. However, it was unclear about how to appoint a Regent to rule on his behalf - there was no legal precedent for this happening. The royal heir, the Prince of Wales and the future king George IV, believed it was his right to automatically become Regent, but the British Parliament believed that they alone had the right to appoint a Regent and that the Prince had no more "right" to the job than anybody else. As it happened, the Prime Minister of the day (William Pitt the Younger) believed that Prince George probably was the logical candidate for Regent, but the arrogant way the not-very-popular Prince went about the whole matter caused a division in Parliament. George III eventually recovered enough to resume royal duties, but the issue remained unresolved.
The token was issued by aristocratic plantation-owner Philip Gibbes, who seems to have advocated "middle path" attitudes to other burning issues of the day (such as the American colonies and the issue of slavery); I don't believe it's otherwise recorded which side of the Regency debate he landed on, but the tokens give evidence we was not a fan of the Prince. The token-issuers support for King George III is also highlighed onthe reverse, where George III is depicted as none other than Neptune. The message of the tokens seems clear: the Prince's job is to serve the government and people, not to please himself, and The Prince might be heir and Regent, but he's not the real King.
Don't say "infinitely" when you mean "very"; otherwise, you'll have no word left when you want to talk about something really infinite. - C. S. Lewis
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