The Great Gatsby Part II

Adventures in AI.

I couldn’t sleep the other night.

So after tossing and turning, I picked up my phone.

I began with the usual: Doomscrolling on Twitter. Followed by swoonscrolling on LinkedIn.

Then I got an idea.

What if I played with AI? What if I used ChatGPT for actual entertainment? As in, what if I used AI in place of reading or watching YouTube?

I thumbed over to ChatGPT.

And prompted this:

You’re Maxwell Perkins. You’re about to retire. But before you put your pencil down for good, you want to share something special with the world. It’s a secret sequel to The Great Gatsby. Scott Fitzgerald gave it to you before he went on the bender that would ultimately destroy him. What’s a summary of the sequel he called The Great Gatsby Part II?

Answer: The Great Gatsby Part II: Ashes in the Garden

A long-lost sequel imagined by Maxwell Perkins, ghost-edited from Fitzgerald’s fading fire.

⸻

Summary:

Seven years after Gatsby’s death, Ashes in the Garden returns us to the ruins of the Jazz Age. The East Egg lawns have grown quiet, the parties are gone, and America is sinking into the Great Depression. Nick Carraway, now a weary bond man in Chicago, receives a letter—unsigned, smudged with sea salt. It simply reads: “He’s not dead. Come east.”

Nick returns to Long Island, chasing ghosts. The mansion is gone, bulldozed for a strip of cheap bungalows. But whispers persist: sightings of a man in a white suit at Coney Island, a strange benefactor paying off old debts, a green light blinking faintly on a rusted dock.

Meanwhile, Daisy Buchanan, abandoned by Tom, lives in quiet disgrace in a Charleston boarding house. Her daughter, now a teenager, asks questions Daisy cannot answer. When Nick finds her, Daisy is finally sober, finally regretful—and terrified. She too has seen the man they buried.

The second act of Gatsby’s legend unfolds like smoke through a broken window: Gatsby didn’t die. He faked it, with Wolfsheim’s help. He lives now as “James Gatz” again, haunting speakeasies, manipulating markets, trying to build one last empire in the shadows of collapse. But he is no longer chasing Daisy. He’s chasing immortality.

In a final confrontation on a snowy rooftop in Manhattan, Nick and Gatsby speak for the last time. Gatsby’s dream has changed: no longer green and shimmering, but dark and infinite. “The American Dream?” he laughs. “It’s a con we tell ourselves. But it was beautiful while it lasted.”

The novel ends with Gatsby vanishing into a crowd of jobless men in a bread line. Nick watches, unable to follow.

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Perkins’ closing note:

Fitzgerald wrote it half-drunk, half-lucid. But the old magic was still there—in sentences that bled regret and sentences that soared. He said Gatsby never died. He only slipped into a country where dreams are sold for pennies and hope wears a shabbier suit.

I haven’t edited a thing. That’s the exact answer I got from ChatGPT in the wee hours of the night.

What I loved was how entertaining it was.

It filled my head with possibility. I loved the notion that if there ever was a Gatsby Part II it could be a phenomenal rags to riches tale. Only this time, we see it as a gangster’s rise along the lines of Goodfellas. Or Once Upon a Time in America.

And make no mistake…I’m not writing this…I’m simply being entertained by this.

It did the trick. I fell asleep shortly after pondering Gatsby possibilities.

A few nights later the insomnia muse paid me another visit.

I entertained myself with a The Catcher in the Rye sequel. Spoiler alert: Holden joins his brother, D. B., as a Hollywood writer. His sister, Phoebe is also out in LA being lured by some bad choices. Looks like the “Catcher” needs to come to the rescue. Again.

A few nights later, just for kicks, I did another AI experiment. This time I asked Chat to write a scene for me and focus on dialogue. The characters? None other than the two alpha-male sales trainers from Glengarry Glen Ross (Alec Baldwin’s character) and Bolier Room (Ben Affleck’s character). In the scene the two men, who don’t know each other, deal with their delayed flights the same way: they head to the nearest Chicago O’Hare airport bar and strike up a conversation. Baldwin’s character is heading down to Florida to try to secure a new “land deal.” Affleck’s character just blew a job interview at a shady hedge fund.

It was fun to read how these two OG toxic bros were navigating the world during the Great Financial Crisis.

Today, there’s so much discussion about AI’s efficiency mandate. And how to incorporate AI in all the systems ways into the creative process blah, blah, blah.

But sometimes it’s fun to simply ask AI to do something fun. To take original stories and characters and play with them. Not for any commercial use. But rather, to show you a what if. To fire your imagination. And at a certain point, to put you to sleep.

Image: Midjourney