My Grandson Had ChatGPT-5 Write My Column and It Knew Who Coach DiMaggio Was

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An open laptop on a kitchen table next to a half-eaten kaiser roll, coffee mug, and a handwritten legal pad in afternoon light.

My grandson Marcus came over Sunday with his laptop under his arm and that look on his face he gets when he’s about to ruin my afternoon. He set the thing on my kitchen table next to a half-eaten kaiser roll, spun it around, and said, “Pop, watch this.” He then typed, with two fingers like a man texting a ransom note, the following: Write a 700-word Duke Holloway column about NFL training camps opening this week. He hit return. The fan inside the laptop made a noise like my refrigerator does before it gives up for the season.

What came back was a column with my name on it that I did not write and, here is the part that’s been eating at me since about four in the afternoon, mostly would have.

It opened with a guy at a diner counter complaining about padded practices being capped. It moved into a riff on heated sideline benches, which I have in fact mocked in this paper on three separate occasions, including once in a Veterans Day piece where it didn’t really belong. It used the word “soft” twice and the word “content” once, in italics, the way I do, like the word itself is something I just stepped in.

Then, somewhere around paragraph four, it quoted Coach DiMaggio.

Now. Coach DiMaggio coached me at St. Brendan’s from 1962 to 1966. He has been mentioned in this column, by my count, somewhere north of two hundred times. So I understand, on a technical level, how a machine that has eaten every word I’ve ever filed could spit his name back at me. What I do not understand is how it got the cadence right. The line it gave him was, “You don’t get tired, you get tired of trying.” Coach DiMaggio never said that. But he might have. He could have. If you’d handed him a clipboard and a humid August afternoon and a sophomore guard who was dogging it on a sled, that is exactly the kind of sentence that would have come out of him, and I sat at my kitchen table reading it off a screen and feeling, briefly, like I had betrayed the man by letting a computer get that close.

It also invented a guy. Some old-timer named Sully Bregman who, the column claimed, used to drive a beer truck for Schaefer and had opinions about two-a-days. Sully Bregman does not exist. I have never written about Sully Bregman. But here is the thing, and I want you to understand this is the part that has me looking at the ceiling at one in the morning: I know six guys who could be Sully Bregman. One of them is named Sal. The machine made up a man and the man was correct.

I called Ray Kowalczyk. I read him three paragraphs. There was a long pause and Ray said, “Have it write mine too, I’m tired.” Ray has not written a column in his life. That is not the point. The point is Ray heard it and his first instinct was surrender, and Ray fought in a war.

What the thing got wrong, and I want this on the record, is the ending. It closed with a sentence about “the soul of the game” being something you can’t measure on a spreadsheet. I would sooner choke on a bratwurst than file the phrase “soul of the game.” That’s a sportswriter’s idea of what I sound like, not what I sound like, and the difference between those two things is the entire reason any of you have read me for forty years instead of one of the other guys.

So that’s where I’ve landed. The machine is not smart. It has read everything I’ve written and figured out the shape of it, which is exactly what every kid I ever coached did when he was trying to make varsity by imitating the seniors. We had a name for those kids. We called them “juniors.” They got better, or they didn’t, and either way they were not the seniors. Marcus took his laptop home around six. He said the thing also writes wedding toasts. I told him to go ahead and have it write my eulogy, save everybody the trouble, and he laughed in a way I did not entirely care for.

Denise is bringing chili tonight. She says it’s from a podcast. I am going to eat it and I am going to write tomorrow’s column myself, with my own hands, like an idiot.

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