Chick's father, Richard, commonly known as "Dick," originally from the North, had for several years been active in the Old Confederacy trying his hand at a number of business projects, none of which, regrettably, had proven successful, and not a few of which, in fact, had obliged him, as the phrase went, to approach the gates of the Penitentiary.
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I mean, right off the start, let's just acknowledge the penis reference in the name Dick. Okay? Now that that's out of the way, let's see what else we've got.
A part of me has always sort of known what a Carpetbagger was and also sort of couldn't rightly explain it but I felt, immediately after reading this, that old Dick Counterfly must have been a Carpetbagger. I think I also read up on it and wiped the sweat from my brow in relief when I discovered I was on the right track and hadn't wasted all that time nearly getting an American Studies minor. I say nearly because I simply didn't want to spend one more semester in college taking one three credit course which would have given me something else to make my dumb father proud of me. What I'm trying to say is I didn't care if my father was proud of me and I was ready to just be done with college.
So here was Chick's father trying to score some easy cash during Reconstruction by either business projects that were probably just legal enough and others that were not legal at all. This is what Pynchon means by "approaching the gates of the Penitentiary" which sent me into a bit of a rabbit hole trying to figure out. It's a hard phrase to read about seeing as how a big section of the Internet has decided that Against the Day is the place to learn about it. Eventually, I found it used in a history book called Mint Juleps with Teddy Roosevelt where the author quotes Quay as saying, regarding people who were possibly paid to vote for Harrison in 1888, how many underlings had been "compelled to approach the gates of the penitentiary." So there's Pynchon using an apt phrase for the time in a way that proves he's a time traveler who does his research by going back to the years covered by his book and just living there while writing the book.
In conclusion, the main point is that Chick's father Dick (ha ha!) was a Carpetbagger.
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