Tag: Jimmy Breslin

Categories
San Francisco/California Writing

The Company of Fog

Note: a little fun this morning with a piece envisioning Jimmy Breslin writing about lunch with Herb Caen at Tadich Grill…

I went to San Francisco to meet a man who writes about the place the way a guy writes about a woman he still wants to sleep with after thirty years.

His name is Herb Caen. He has been telling this city about itself every morning since before most of the people reading him were born. They call him Mr. San Francisco. In New York we don’t hand out titles like that. In New York you earn the right to be called a son of a bitch, and you take it as a compliment.

We met at Tadich Grill. Open since the gold rush, and it still looks like it never got the news that things change. Dark wood. White tablecloths. Waiters old enough to remember when the bridge was new and still sore about it. The fish comes out of the water and onto the plate without a lot of conversation in between.

Caen was already sitting when I got there. Neat. Jacket. That California tan that never quite goes away, like the sun signed a contract with him. He stood up and shook my hand like a man who has shaken a lot of hands and still means it. I ordered a martini, because when you’re in another man’s town you drink what the town drinks, even when the town is wrong.

He had one too. Stoli, twist. He called it Vitamin V.

We talked about columns. About writing for a city that never sleeps against writing for one that takes long naps in the fog and calls it lifestyle. I told him New York will rob you and hold the door on the way out. He said San Francisco smiles while it’s doing it, then writes a nice item about your necktie.

He works in three dots. Little pieces, one after another, like a man feeding a parking meter all day instead of buying the car. Gossip, jokes, the name of whoever just opened a place on Union Street. I need more room than that. I need to turn around. He said my way was fine if you like carrying a piano up the stairs every day. I told him his was fine if you don’t mind never sitting down long enough to find out what you actually think.

The sand dabs came. Caen looked at his like a priest looks at the host. I ate mine like a man who skipped breakfast. Everything on that table was good — the bread, the butter, the light coming in off the street looking like it had been there as long as the wood and knew it.

He leaned in. “You know the difference between our two cities?”

I waited.

“In New York, the people are the story. Here, the city is the story. The people just get to live in it for a while.”

That’s a hell of a thing for a man to say about his own hometown — that the place is bigger than everybody in it, including him. I told him about the man who dug Kennedy’s grave, the one nobody else thought to ask. Caen nodded. He understood the assignment. It was the only time all lunch he didn’t have a joke ready.

We stayed too long. The martinis did their work. Outside, the fog came in soft and certain, the way it does out there, like it’s been rehearsing. Caen put his coat on like a man who has never once been in a hurry. I put mine on like a man who has somewhere else to be, even when he doesn’t.

On the sidewalk he tipped his hat. An actual hat. Nobody tips a hat in New York anymore. We’re too busy hailing something.

“Come back,” he said. “The city likes company.”

I walked toward the cable car line, the fog thick enough to make the streetlights float like they’d given up on the ground. Two men, two ways of loving a place. One writes it in little pieces that catch light for a second and go dark before the next one starts. The other digs until he finds the one man nobody else remembered to ask about, and doesn’t stop until the shovel hits something.

Neither of us was going to change. Neither was the city. That’s probably why we got along.

I caught the cable car and rode it a few blocks just to feel it move under me, the way you touch a thing to make sure it’s real. Behind me somewhere, a man who’d spent his life telling San Francisco it was beautiful was walking home through the fog he’d helped invent — which is either the best job in America or a life sentence, and he never once let on which.

I never did find out if he got tired of saying the same true thing a different way every morning. I didn’t ask. Some men you let keep their secret. Besides, I had my own city waiting, and it doesn’t smile at you while it robs you. It just takes the money and tells you to have a nice day.

Categories
AI AI: Prompting

The Price of the Barstool

Some genius out in California — one of the AI guys, the smart ones, always the smart ones — says the trick to getting a machine to understand you is to stop typing and start talking. Ramble for ten minutes, he says. Total mess. Say whatever’s in your head, contradict yourself, circle back, don’t clean it up. The machine, he says, is better at finding what you meant than you are.

I could’ve told him that thirty years ago for the price of a cup of coffee, except I would’ve told him to go find a bartender.

Every good bartender in this city has been doing this since before anybody could spell computer. You sit down, you’re a mess, you talk for twenty minutes about your ex-wife and your kid’s tuition and the guy at work who’s getting the promotion you should’ve gotten, and it comes out in no particular order, and somewhere in the fourth minute you say the one true thing — I think I’m afraid I already peaked — and the bartender doesn’t say a word, just wipes the bar down in front of you, and by the time you leave you know something about yourself you didn’t know when you walked in. Nobody paid Sam a nickel for that. Nobody gave him a paper to publish.

Now they’ve built a machine that does the same trick and they’re calling it a pattern. They put it in a paper. Somebody in Palo Alto’s going to raise money on it.

Here’s what I’ll say for the guy — he’s right, and being right is rarer than people think in that business. The mess is where the truth lives. Nobody ever said something true the first time they tried to say it cleanly. You clean it up too fast, you’ve written a memo. You let it run messy, you’ve said something.

But I’ll tell you what he won’t put in the paper, because it doesn’t fit on a slide. The machine will hand you back a cleaner version of your ten minutes, and it’ll sound better than what you said, and half the time it’ll be missing the one part that was actually true, because the true part usually comes out sounding wrong the first time. That’s the part a bartender knows and a machine doesn’t. Sam wouldn’t have cleaned up your sentence. He’d have just remembered you said it, and brought you another one, and let you sit there with it.

They’ll charge you a subscription for the part where it listens. The part where somebody sits with what you actually said — that’s still free, if you can find the right stool.

Categories
Reading Writing

The Starting Five I Keep

On November 25, 1963, every journalist in America was at Arlington Cemetery covering the state funeral of John F. Kennedy. Jimmy Breslin went to find the grave digger.

His name was Clifton Pollard. He was paid $3.01 an hour. He had been called in on his day off because the foreman thought he was the best they had, and the foreman was right about that. Breslin spent the morning with him while the ceremony unfolded a few hundred yards away — the dignitaries, the riderless horse, the flag folded into a triangle and handed to a widow. Pollard ate a ham sandwich and kept working.

The piece Breslin filed that afternoon is still taught in journalism schools sixty years later. Not because it covered the funeral better than anyone else. Because it didn’t cover the funeral at all. It found the true subject by ignoring the announced one.

That instinct — turn away from the obvious, walk toward the unglamorous specific, trust that the universal is hiding there — is the one idea I’ve returned to more than any other. It shows up in two very different writers who occupy, in my mind, the same position on the roster.

Breslin got there through deadline fury and a saloon-bred instinct for where the real story was breathing. He didn’t theorize about it. He just did it, on a deadline, in a city that rewarded the loud and the fast. John McPhee got to the same place by an entirely different route: patience, structure, and a willingness to spend six months learning how canoes are made or what happens to a piece of shad on its way up the Delaware River. Breslin worked like a man catching a cab. McPhee worked like a man building a cathedral.

But the underlying claim is identical. If you stay with a specific, unglamorous subject long enough — if you resist the pull toward the obvious center — it will eventually yield something that couldn’t have been reached directly. Pollard and his shovel. The orange grower and his grove. The nuclear physicist who also happens to be a canoe builder. The method is the same. Look where no one else is looking. Wait longer than feels reasonable. Write what you find.

This is one player, really. Just wearing two different jerseys.

The second seat belongs to Wright Thompson — not a single book but a stance. The premise that the most revealing place in any story isn’t the event itself but the moment before and after it, when the subject is alone with something they haven’t yet put into words. Every piece in this tradition is quietly asking: what is this person carrying that they can’t say out loud? It’s a question that turns out to apply well beyond sportswriting. It applies to most things worth writing about.

The third is whatever the Apple design era taught about constraint and clarity. Not nostalgia — something more durable. The idea that removing something can be an act of confidence. That the most useful things often appear to be doing less than they are. This one surfaces constantly in writing, in argument, in the editing pass where you decide what the piece actually needs versus what it accumulated along the way. Features are easy to add. Knowing what to cut requires a different kind of certainty.

The fourth is the philosophy embedded in spaced repetition — not the algorithm but the claim underneath it. That knowledge you don’t revisit isn’t really yours. That understanding decays on a predictable schedule whether you acknowledge it or not. The honest response isn’t anxiety about this; it’s the habit of return. Going back to the same passage, the same idea, the same question on a different day, and finding it has changed — or finding that you have.

The fifth seat shifts. That’s probably the right design. Four constants and one that evolves is roughly the correct ratio for a starting lineup that has to play in different eras. Right now that seat belongs to the question of what AI does to a practiced human sensibility — whether it erodes it by substitution or clarifies it by contrast. Earlier it was held by a certain kind of systems thinking. Before that, something else. The player who earns that spot is always the one asking the question the current moment most needs answered.

The coach who wins five championships doesn’t do it with the same roster. But he does it with the same philosophy. The starting five aren’t the players who happened to be good once. They’re the ones who keep earning their minutes regardless of what the season throws at you.

Breslin knew where to find Clifton Pollard because he’d been looking in that direction his whole career. The skill wasn’t the story. The skill was knowing that the story was never where everyone else was standing.

That’s the one I keep coming back to.

Categories
Writing

Breslin And Hamill: Deadline Artists

I recently watched the HBO/Max documentary Breslin And Hamill: Deadline Artists about the great New York newspaper columnists Jimmy Breslin and Pete Hamill. A featured review on IMDB notes: “Two of the most influential reporters of the 20th Century were similar to each other in many different ways, couldn’t be more different from each other.”

A few weeks ago I watched a Library of America webinar on the publication of a new volume collecting Breslin’s work: Jimmy Breslin – Essential Writings. Titled Deadline Artist: The Genius of Jimmy Breslin, the session included the editor of this new volume, New York Times writer Dan Barry along with Mike Barnicle and Mike Lupica – all of whom knew Breslin well. Barnicle and Lupica also make appearances in the HBO/Max documentary.

Continue reading “Breslin And Hamill: Deadline Artists”
Categories
Writing

A Jimmy Breslin for Our Time

The late, great Jimmy Breslin was the embodiment of a classic New York newspaper columnist. He chronicled the gritty underbelly of the city, the backroom deals, and the voices of the overlooked. With his uncompromising style and passion for giving voice to the ordinary men and women of the city, Breslin shined a light on the harsh realities and human stories that those in power often overlooked or tried to brush aside.

Breslin’s columns were marked by his streetwise writing, caustic wit, and deep empathy for the working class. He had a masterful way of cutting through the spin and official narratives to excavate the truth. Whether he was covering brutal crimes, civic upheaval, or clashing with the city’s elite, Breslin’s journalism emanated from spending hours walking the streets, talking to people, and seeing New York through their eyes. Breslin wasn’t an outsider looking in. He understood the city’s soul.

While the technology beat may seem worlds apart from the gritty NYC stories that Breslin staked his career on, we are fortunate to have our own modern-day commentator holding the tech industry’s feet to the fire: the inimitable Kara Swisher.

Like Breslin, Swisher has been entrenched in the tech world since its early days. She knows the players, the rivalries, and the unspoken rules, allowing her to cut through the PR spin. She has cultivated a signature voice – part insightful analyst, part merciless interrogator that the most powerful figures in tech have learned to respect and, sometimes, fear. Her refusal to cozy up to the wealthy and influential is reminiscent of Breslin playing hardball with Tammany Hall bosses and corrupt officials.

Both writers leaven their seriousness with a healthy dose of humor. Breslin’s sardonic wit made his columns even more impactful. Swisher’s sharp barbs and clever turns of phrase keep readers engaged and entertained. Both are very enjoyable to read.

While many in the tech press stay firmly situated in the industry’s vortex of product launches and funding rounds, Swisher is unafraid to step out of the echo chamber. She understands that tech is not just about the latest iPhone or who gets funded, but about the human consequences – both wondrous and troubling – of the technologies reshaping our world.

Swisher’s columns and interviews, whether deconstructing a social media giant’s PR missteps or grilling a tech luminary, are filled with granular insights and skeptical questioning. There is little deference shown to reputations or famous names. Like Breslin’s tenacious reporting, her approach exposes uncomfortable truths that those in power often would prefer remain hidden. Breslin’s New York was a physical landscape, while Swisher navigates the virtual one. But they share a core mission: to shed light on the forces shaping our world, and to give voice to those who might otherwise be unheard.

Crucially, both journalists share a profound sense of empathy that fuels their crusades against injustice and the abuse of power. Swisher’s fierce advocacy for technology workers, consumers, and other often overlooked stakeholders echoes Breslin’s signature move of giving voice to the voiceless. Her commentary is a clarion call for accountability in an industry intoxicated by its own lofty self-perceptions.

While the subjects of their writing were completely different, Jimmy Breslin and Kara Swisher are united in their roles as civic guardians – unwilling to be cowed, determined to upset institutional hypocrisy, and most importantly, upholding the vital responsibility of the free press. In an age of all too often obfuscation and empty corporate platitudes, we are fortunate to have Swisher carrying Breslin’s torch.

This post was stimulated by attending a Library of America webinar earlier this week on the publication of a new volume collecting Breslin’s work: Jimmy Breslin – Essential Writings. The webinar titled Deadline Artist: The Genius of Jimmy Breslin included the editor of this new volume, New York Times writer Dan Barry along with Mike Barnicle and Mike Lucpica – all of whom knew Breslin well. It was wonderful hearing some of their stories about Breslin, his writing and his escapades.

During the webinar, these writers pointed to an article of Breslin’s which they say has become very well known and is taught in journalism schools around the country: “The Gravedigger”. In this essay, taking place on the day of the funeral of John Fitzgerald Kenney at Arlington National Cemetery, Breslin focuses on Clifton Pollard who dug JFK’s grave.

Just prior to this essay, Breslin’s wrote “A Death in Emergency Room One” which takes us inside the emergency room at Dallas’ Parkland Hospital with the physicians attempting to save the president’s life. Both of these essays are quite remarkable to read now some sixty years later. They really illustrate Breslin at his contemplative best.

I just finished reading Burn Book: A Tech Love Story, Kara Swisher’s great new memoir about her life and times as a tech journalist – and so much more. The videos from her book tour are also a delight to watch: especially this one held at the Commonwealth Club in San Francisco with Kara in conversation with Reid Hoffman. Another is this one sponsored by the Washington, DC bookstore Politics and Prose that was moderated by Laurene Powell Jobs.