One that always bothers me is Pie Traynor. His autograph itself has absolutely no style or flair (in an era when most players took pride in their signature). But more irritating is that the guy had absolutely no feel for where to place the signature.
Whether it's on an index card, trading card, photograph or ball, he always crammed it into a ridiculously tight and illogical spot. Typically relegated to an obscure corner, or right up against a border (so you can't effectively mat it) or touching on the laces of a ball.
The concept of signing a sweetspot or side panel apparently never occurred to him. No matter what the medium, the result was almost always aesthetically displeasing.
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