Saw this question go by in my referrer logs, thought it was an interesting topic we don’t usually cover.
Here’s my understanding of Shakespeare’s dad.
Shakespeare’s dad was a relatively well regarded business man (a glove maker), and member of the community, holding several political positions. He got into some trouble for illegal dealing in wool, and his debt got to the point where he would no longer attend church for fear of being arrested. Eventually he dropped out of public life completely. He did at one point apply for a family coat-of-arms, which was eventually granted in 1596 when son William applied for one on behalf of his father.
John Shakespeare actually held numerous public offices including burgess, chamberlain, alderman and ultimately bailiff, which was the rough equivalent of mayor. So he was well connected, well liked and respected in his community to keep moving up the political ladder.
There’s evidence that he was involved in usury – lending money with interest - something on which his son would have something to say later in Merchant of Venice. He was apparently good at it, as records have him associated with a loan of money that would today be worth more than $50k. This, however, was highly illegal at the time, subject to fines equal to all of the loaned money, plus interest, fines, and still imprisonment on top of that. Risky business.
If he was so successful in his political career, why did he turn to the shady dealings? My guess is that he was a man of entrepreneurial spirit who had his hands in many things, and as he got closer and closer to “the line”, sometimes maybe he stepped over it – knowingly or not. But once you step over it, reap your profit and don’t get caught, then guess what? You’re going to want to hang out on the wrong side of the line again. It’s like a gambling addiction. You tried it, you won, you liked it. You tried it again, oh hey look, you lost. Now you’re screwed, but now you keep playing because you feel the need to get even and win it back. I suspect John Shakespeare had much the same issue.