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 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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 His story, as clearly as could be made out among the abrupt changes of register which typify the adolescent voice, exacerbated by the perilousness of the situation, was as follows.

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"His story" reads as history therefore this entire sentence should be read as a commentary on history. Don't @ me.

See, what Pynchon is saying is that the United States was still young when the War Between the States happened and so, in documenting it, it might not have been told clearly and thus subsequent attempts to make the United States better were muddled in the miscommunication of what actually happened and therefore we're all still paying for the United States' sins. See, it's hard to tell the truth in a "perilous situation," meaning that the accounts of time were subject to the rebuttals and accusations and remonstrances and, above all, the violent acts of the rebels who tried to divide our nation to maintain the right to keep other people as slaves.

So the history of the adolescent United States could not clearly be made out due to the inefficacy of its adolescent voice and also because it was being constantly threatened by rough vandals and white supremacists.

Go ahead. Just tell me that isn't what's being said here!

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 Two weeks previous, beside a black-water river of the Deep South, with the Chums attempting to negotiate a bitter and unresolved "piece of business" from the Rebellion of thirty years previous—one still not advisable to set upon one's page—Chick had appeared one night at their encampment in a state of extreme fright, pursued by a band of night-riders in white robes and sinister pointed hoods, whom the boys recognized immediately as the dreaded "Ku Klux Klan."

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I have often wondered how American conservatives can enjoy any kind of storytelling entertainment (books, movie, comics, television, music . . . you know, all of it, really) when the protagonists of those stories are often fighting against everything the American conservative believes in. At least, I had often wondered this until recently when I realized right wing talk radio and right wing television news programs became a thing to fill the entertainment vacuum for American conservatives. No wonder they watch and listen to the propaganda spewing assholes all day long because other forms of entertainment constantly remind them that they are the villain to be fought against. Of course you'd want to watch something that told you that your values were those of the hero and that the other people were terrible socialist monsters who wanted to destroy you and your family and, most especially of all, your precious guns.

For those who still wanted to be entertained, you would have to come up with a different tactic than simply immersing yourself in right wing propaganda and that would be attacking media entertainment outlets for getting too political in their stories. You would then argue that stories used to be non-political and simply entertaining after which you would not point to any past examples because those don't exist. All stories are political when the politics you've chosen are selfish, cruel, and without any sacrifice for the greater good. All stories appear political when you constantly see yourself as the villain. Instead of engaging in self-reflection and thinking, "Am I the baddie?" [Thank you, Mitchell and Webb], they simply condemn the thing that made them feel bad. And then they paint that as some new form of political correctness gone mad instead of realizing that the little guy fighting back against injustice has always been the core of most stories. They just didn't see it that way until they embraced the injustice. All of a sudden, every story was an attack on them.

The only protagonist an American conservative can identify with is Ebenezer Scrooge and he's tormented until he gives up his American conservative values! The greatest and most uplifting look at Earth's future is Star Trek: The Next Generation and it's a socialist utopia where they don't even have money! I don't know what they're always gambling for when playing poker but I assume every chip can be redeemed for oral sex. How do they see inclusivity and universal health care and the elimination of poverty and helping anybody who needs help as terrible acts that will destroy our country? Oh, I think that question answers itself. Those things will destroy what they think of as their country. They might support the same thing American progressives support but they only support those things for certain people. Some people are deserving of life; some people are not.

And that's sort of what sent me on this tangent: the introduction of the Ku Klux Klan in this line by describing them as "dreadful." They're bad guys and Pynchon doesn't need to waste any space showing the reader why they're bad. We just know it. Here are some people described as chasing a boy through the night in sinister hoods and when it's revealed that it's the dreaded Ku Klux Klan, the reader just thinks, "Yeah. Of course it is. Jerks." That line is a lot like the movie Get Out. It's revealing in how the audience reacts to it. The story isn't telling you what to think or feel; the way you wind up thinking and feeling tells you how true the story is. Who reads this line and thinks "Hey wait a second now! The Ku Klux Klan had some good programs and ideas!"? A terrible person, that's who. And who can watch the final scene of Get Out and not feel the tension and despair and fear when the cop car pulls up, a scene that has been played over and over in white horror movies as a way to release tension and to say, "Everything is safe now. The horror is all over"? A person who is defending terrible ideologies and denying reality is who.

Now that that's out of the way . . . what is this unresolved "piece of business" that the Narrator feels is still, thirty years on, inadvisable to make a Chums of Chance book out of?! What are they up to?! This reeks of conspiracy! And a conspiracy that must revolve around slavery! I demand a Chums of Chance book about this post-forthwith even if the other Chums of Chance books don't actually exist! This book could blow the doors off the General Lee! And you know how hard that would be seeing as how they were welded shut!

This line also humanizes Chick a bit more. Rather than seeing the aloof, rebellious loner who doesn't quite fit in, we see a young boy scared for his life seeking help from others. The very antithesis of who we, the readers, thought he was! I love Chick so much more now (and I loved him—or her, maybe—a lot already).

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 Even allowing for his irregular history—a mother, so it was said, vanished when he was yet a babe—a father, disreputably adrift somewhere in the Old Confederacy—Counterfly's propensity for gratuitous insult had begun to pose a threat to his probationary status with the Chums of Chance, if not, indeed, to group morale.

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It seems to me, Lindsay's concern for Chick Counterfly has nothing to do with Chick Counterfly. That's why he "frowned in perplexity." Because he doesn't know how to berate Chick into falling in line without looking like a jerk, seeing as how Chick Counterfly's family situation makes him a sympathetic character to the other members of the crew. We already saw how Miles Blundell bit his tongue when Chick insulted him out of respect for Chick's pathetic upbringing in a vulgar and low social environment. But Lindsay has "group morale" to think about. Because if "group morale" falls, things aboard their tiny airship might get dangerous. And dangerous working conditions can lead to a truly terrible conclusion: loss of profits!

Okay, sure, maybe Lindsay cares about the crew and he's truly thinking about the crew's safety is an argument somebody might make who forgot they read that part where Lindsay dangles Darby dangerously over the side of the airship as punishment.

Lindsay sucks.

We get a little bit of Chick's history from this line which sets up some future drama if Pynchon decides he needs more drama later. Who was Chick's mother? Where did she go? Why did she abandon him?! Why is his father disreputable? What's he doing in the Old Confederacy? Might he come looking for his son someday, purporting to have missed him all these long years but, in reality, attempting some huge con to get his son's money? That's a plot which always comes up with estranged fathers in sitcoms, right? Usually in a poignant episode that downplays the laughs and which ends with everybody hugging after they stand up to the charlatan father.

We also learn Chick has probationary status with the Chums of Chance. Earlier we learned he was the newest member (as even the Narrator is unsure how he might act in various situations) and now we learn that he's not yet a full member. But even Lindsay won't boot him out of the organization. Mostly for Lindsay's own sake, of course, in that Lindsay doesn't want to come off as an unfeeling jerk in the crew's eyes. Although what are the crews' feelings for Darby if Lindsay can swing him around over the side of the airship without Lindsay worrying about what people might think of him? Darby must be just annoying enough to everybody on the ship that they don't mind him getting comeuppance every now and again.

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 Hearing this, Lindsay Noseworth frowned in perplexity.

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The "this" which Lindsay heard was Chick Counterfly insulting Darby Suckling's work ethic. That upset Lindsay. Remember, Lindsay is the guy who just held Darby over the side of the Inconvenience for doing nothing, really. He threatened a member of the crew's life because that crew member "spoke informally." But now Lindsay acts sad and confused that Chick Counterfly has called Darby a saphead for risking his life for The Man. Lindsay is telling on himself.

For Lindsay, it's okay for a person in charge to threaten the life of the workers for any thing that he thinks might interfere with the work. One of those things that might interfere with the work is one of the workers telling another worker that they're an idiot for accepting the mortal dangers of work that has little meaning in the overall scheme of things. To possibly trade your life for a mere wind reading when, from the deck of the gondola, you can get a pretty good idea of what the wind's doing is a sucker's game. But voicing that reality is not something a foreman or manager or owner or Second-in-Command can allow. Because it goes against the work. And to the person in charge, the work, or the bottom line, is more important than the worker.

Chick Counterfly has just brought the stink of unionizing onto the Inconvenience with a casual insult.