Well- the first thing we need to establish is that rhyming was rather popular in English for a spell. Cockney language came from that- even the whole “soccer” “football” thing (which I’ve discussed before) came about in part through word games and rhyming.
So- way back in history everything was written by hand, and people liked to rhyme. A long name would often be shortened. “Richard” on paper might become “Ric” or “Rich.” These have rose to nicknames like “Richie” and “Rick.” “Rich” became “Hitch” when rhymed, “Rick” became “Dick.” This isn’t uncommon. William becomes “Will” and then Rhymed becomes “Bill.” “Robert” became “Rob” and then rhymed was “Bob.” There are actually TONS of nicknames we don’t often hear for these names because they fell out of popular use- like “Rick” was sometimes nicknamed as “Hick.” In modern times- “Hick” isn’t a common English name and is even a slur for certain rural folk. Back then though- it was just a play on a name.
Speaking of- “Dick” also can be a jerk or a penis. How’d that happen? Well- we don’t REALLY know. We do know that the earliest recorded use of “Dick” in either of these ways is hundreds of years after it was a name- so the name most likely came first. Around the 16th century “Richard” started to be synonymous with “man” in much the way that “Jack” or “John” are used as “default” men’s names- how Americans might say if someone is displaying traditionally feminine attributes they are a “Nancy” or Australians might call a woman a “Sheila,” or the classic phrase “every Tom dick and harry” to refer to a random group of people.
So “Richard” came to mean “every man” as a general slang turn of phrase. It’s possible “Dick” as the diminutive of Richard was used for “penis” as a play on “my little man” or the anonymous nature and eponymous presence of “Dick.” The term “Dick” as a penis is frost seen is written use by British soldiers around 1890. Of course- the root meaning of “Richard” is “Hard ruler” which MIGHT have played in to its use as a term for a penis- but there isn’t a (forgive the unintended pun) hard case for that or much support. It’s possible though.
Speaking of “Hard ruler” dick is recorded to be used to mean “jerk” by at least the 16th century. Wether the two could be related is also speculative. There were several rulers in European history named “Richard” and perhaps the two are linked- the origins of “Dick” as “jerk” are likewise shaky- but at least in writing, to date- the name/nickname came first, then the use as “jerk” then the use as “penis” all separated by hundreds of years. It could of course be a coincidence- “trump” has been an English word since about the 16th century. Derived from “triumph” the word was used in card games such as bridge where a “trump card” was a specific move- but came to use outside games to mean to “to get the better of.”
Now- 5 centuries later a major world ruler is named “Trump,” and he happens to have a style and persona where he is prone to attempt to “trump” others- and certain of his own traits “trump” things like decorum or other human traits- thusly it might be difficult for a historian to look back through records centuries from now and sort it all out- with the word “trump” and the name “Trump” being popular use and prominent in their times- unrelated but casually linked in some ways- and slang uses originating from the name trump- often in negative context.
So looking at a pejorative use of the word as slang from a future vantage where perhaps the man who holds the name is obscure in history as being a topical fad but not a lasting name (one of over 80 presidents by current thrust of one is looking back hundreds of years from the future), one might overlook or lack the popular culture context to frame such uses as based around the politician and be flummoxed as to how the word could differ so from its original use. We do tend to keep much better and more detailed records than past generations- but that causes its own problems and there are many who say due to the digital nature of much of our information that our well kept records won’t endure centuries.
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Lemme be your ruuuuuuler