My two cents, not worth much but I think there are three main reasons the trend to illegibility...
1) As has been stated in previous posts, penmanship, cursive, heck writing is no longer taught in most schools. With the advent of keyboard input and texting, the need to write for most younger folks is less and less, so there is no "practice". I think even the practice of drafting, where one learned to pen perfect block letters, has been supplanted by CAD computer software.
2) In the 1990s I discussed autographs with an athlete friend of mine and he surprised me with the comment that agents were advising against signing autographs for fear of identity theft and that if they did want to sign autographs that they should develop a "mark" that was different than their signature on legal documents.
3) This is conjecture on my part, but with the rise of eBay the numbers of people seeking autographs has risen (opportunists thinking they can profit from the autographs AND/OR the perception that an autograph has some intrisinc $$$ value), and those players who do want to sign autographs have to shorten the time it takes to sign as much as they can. One can see how a player in the minors may have a semi-decent autograph but as the years go by it gets worse and worse.
In today's society, when meeting someone famous, selfies have replaced the autograph so it will be interesting to see how "social distancing" affects this in the coming years. I imagine that access to famous people will get even harder now.
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