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It makes no sense to me. Dick sounds absolutely nothing like Richard. Other English nicknames confuse me as well. Bob for Robert, Bill for William, Jim for James, though they are still a bit closer to their original than the whole Dick-Richard of it all.
Edit: as someone mentioned in the comments, "Jack" as a nickname for "John" is another interesting one.
It originates from the 12–13th centuries (Middle English), in a time where a lot of people had the same names. Richard was also spelled Rickard, which obviously shortens to Rick (a nickname we still use today). From there, rhyming forms were created, getting us Dick. It also created Hick, which is a nickname that isn't in use today, but it's the origin of the word hick, in addition to last (family) names such as Hickson which are still in use.
The book Christian Names in Local and Family History expands further on this:
We can see immediately how this might give rise to Roberts and Robertson and how the pet form would lead to Robb(s) and Robson and the diminutives to Robbins, Robinson and Robbie. Rhyming forms would produce Dobbs, Dobbin, Dobbinson, Hobbs, Hobson, Hopkins and Hopkinson. Similarly the pet form 'Dodge' for Roger gave rise directly to the surnames Dodge and Dodgson, Hodge and Hodgson, and the diminutives produced Hodgett, Hodgkin and Hodgkinson. Such developments were not confined to the common names nor indeed to male names, and the process is one that is familiar to anybody working on early records. The purpose here though is simply to remind those who are not familiar with such practices what can lie behind latinised forms such as 'Robertus' and 'Ricardus'.
This was created the same way (rhyming) as the other names in this group, but with more intermediary steps. From the Dictionary of Medieval Names from European Sources:
Margaret is the radiconym; take it and cut the name down to the first syllable, and you get Marg. In certain dialects, that r is going to be very lightly pronounced, giving us Mag. Magge (pronounced with two syllables) can be found in England as early as 1200, and not much later after that, you can find that hypocoristic form augmented with a diminutive suffix: Magota 1208 (this is a Latin form and would’ve been Magot in the vernacular). (We’ll give you three guesses as to why this name is no longer popular today….). By the end of the century, there are examples of the -a- shifting to -e-, e.g., Megge 1254, 1275, 1279, etc. You can also see it in Megota 1309 (also Latinized).
Even scholars don't agree on the exact origin!
It's likely one of these:
Summarized from The Kinship of Jack: I, Pet-Forms of Middle English Personal Names with the Suffixes -kin, -ke, -man and -cot.
Middle English had James, Jame, and Gemme. From there it's a simple vowel change to get to Jim.
The wikipedia entry for Dick (nickname) says it likely originated via rhyming slang for Rick, which is another nickname for Richard.
Similar answers apply to your other examples. The answer now is that they are idiomatic and traditional, even if they don't make much sense.
‘Dick’ evolved via rhyming slang out of ‘Rick’, which is a reasonably standard clip form of ‘Richard’ (and that clipping down to ‘Rick’ makes a lot of sense if you consider the typical English approximations of the German pronunciation of ‘Richard’, or how ‘ch’ is typically pronounced in other languages of the British Isles).
‘Bob’ is a similar case of rhyming slang evolved out of ‘Rob’ which is in turn a clip form of ‘Robert’. Usage of ‘Bob’ for ‘Bill’ is not something I’ve personally heard, but I could easily see it as an alliterative substitution that just happened to stick in some micro-dialect.
‘Bill’ itself is yet another case of rhyming slang evolved out of ‘Will’ which is in turn a clip form of ‘William’ (or ‘Willard’).
‘Jim’ is an Anglicization of the Scottish ‘Jem’, which is an old clip form of ‘James’.
At this point, all of them are established forms in English, and that unfortunately means they don’t have to make sense. Etymology of names is often confusing in general (consider for example that John, Sean, and Evan are all different forms of the same name that arrived in the English language via different routes), and nicknames just make it worse.
Rather than rhyming slang, which is a fairly intellectual application of euphemism (fart, raspberry tart, raspberry), I believe rhyming nicknames arise from older siblings who haven't quite learned to talk. It's a common phenomenon. For example, the name "Buzzy" sometimes derives from "brother" (Buzz Aldrin, Curtis "Buzzy" Roosevelt).
Remember that the "r" in "Richard" would have been pronounced with the tip of the tongue several centuries ago, and a child learning to talk could easily mutate an apical alveolar /r/ sound into /d/.
Are there no parents on this thread? My daughter Laura was "Laura-Paura", Pamela was, sometimes, "Pamela-Bamela", sometimes I just called her "Panama". "Anna" to "Anna Banana" is common. Don't tell me that rhyming nicknames aren't a thing! Those who distinguish this from rhyming slang are correct, though. Rhyming slang is when you construct a non-rhyming slang synonym from a rhyming intermediate phrase. If I had called Anna "Dolly" because Anna-Banana -> Dole Bananas -> Dole -> Dolly, that would have been more like rhyming slang.
