In his tattered, single-breasted frock-coat, buttoned meagerly up to his chin, the shutter-brain made him a bow, which, for courtesy, would not have misbecome a viscount, then turned with silent appeal to the stranger. But the stranger sat more like a cold prism than ever, while an expression of keen Yankee cuteness, now replacing his former mystical one, lent added icicles to his aspect. His whole air said: "Nothing from me." The repulsed petitioner threw a look full of resentful pride and cracked disdain upon him, and went his way.
"Come, now," said the cosmopolitan, a little reproachfully, "you ought to have sympathized with that man; tell me, did you feel no fellow-feeling? Look at his tract here, quite in the transcendental vein."
"Excuse me," said the stranger, declining the tract, "I never patronize scoundrels."
"Scoundrels?"
"I detected in him, sir, a damning peep of sense—damning, I say; for sense in a seeming madman is scoundrelism. I take him for a cunning vagabond, who picks up a vagabond living by adroitly playing the madman. Did you not remark how he flinched under my eye?' (36, 45-49)
Talk about icing somebody out. Winsome gives zero cares for you if you're in need of money. He's also pretty suspicious of this poor man's mental state. He argues that since the dude isn't completely insane, he must be faking. We're starting to think Melville's trying to tell us it's a pitiless world out there.
"—tell me, was not that humor, of Diogenes, which led him to live, a merry-andrew, in the flower-market, better than that of the less wise Athenian, which made him a skulking scare-crow in pine-barrens? An injudicious gentleman, Lord Timon." (24, 56)
Name-drop time: who exactly is Diogenes? Glad you asked. He's a cynic from classical Greece who wasn't too impressed with society or its leaders, people like Alexander the Great. His claim to fame? He hung out in a tub in his birthday suit in public making a ruckus.
So why's Diogenes brought up here? Well, Frank is trying to get Pitch to party—you know, be the opposite of a misanthrope. In order to do that, he says that if Pitch is going to be a grumpus, then it's better to be a grumpus like Diogenes, who used to hang out being wild and crazy in the town center, rather than a grumpus like Timon of Athens, another misanthrope who ran away into the woods and bellyached all the time about how bad everybody was. He didn't come to a good end.
"Your hand!" seizing it.
"Bless me, how cordial a squeeze. It is agreed we shall be brothers, then?"
"As much so as a brace of misanthropes can be," with another and terrific squeeze. "I had thought that the moderns had degenerated beneath the capacity of misanthropy. Rejoiced, though but in one instance, and that disguised, to be undeceived." (24, 57-59)
Pitch misunderstands Frank. When Frank invokes Diogenes, Pitch thinks that after all, Frank must just be a regular misanthrope himself. Apparently, Pitch is cool with a brotherhood if that bro-life means hating on others. For Pitch, this "revelation" gives him faith in humanity, that there are still people out there who…hate humanity. Irony alert.