The first time I interviewed Herb Kelleher for a magazine profile, the then CEO and chairman of Southwest Airlines told me a dirty joke. This was minutes after he had greeted me in a hallway, walking me to his windowless office. Along the way, he stopped to kiss a few female employees — on the lips — and he hugged a couple of male employees as if he might never see them again.
It was summer in Dallas. It was hot. I was twentysomething and sweating through an ill-fitting suit. Once we’d made it to his office, Herb insisted I remove my jacket, then my tie, then roll up my sleeves. Then he offered me a glass of water and told me he preferred whiskey to water. He said he was simpatico with Dorothy Parker or W.C. Fields or, well, someone, about that. “I never drink water,” Herb said, smiling wryly. He paused briefly for effect. “You know, fish fuck in it.”
That was two decades ago. I was doing only my second big magazine profile. The story, for this very magazine, would win an award and would become the backbone of my earlier career — the best clip I had for years and the story that eventually landed me a job covering the White House for Investor’s Business Daily. I’d always meant to thank Herb for that, to tell him how easy he’d made it for me — a sweaty, stammering kid — to look like I knew what I was doing. You couldn’t write a bad story about Herb. He was too much of a character. He drank, he smoked, he told dirty jokes. He told Wall Street to go to hell, said he’d run his company his way. He was whip smart, well spoken, thoughtful, and bonkers successful. The hardest part of writing about someone like that was landing the interview. I could not have messed it up.
Although, to be sure, a lot of people today have messed up one thing about Herb. If you’ve read stories (like this or this) that cite the thing about Herb and Rollin King co-founding Southwest over drinks and sketching their business plan on a cocktail napkin, you’ve read fiction. Those guys had drinks. Plenty. And they talked about a business. But Herb thought the idea was stupid, which he himself told me. And there was no sketch. King told me that years before his death in 2014.
But much of the other stuff you’ll read about Herb today is true. He really did care about his people. Those weren’t just platitudes he’d offer about putting Southwest’s people first, customers second, investors third. He meant that stuff. And he really did work 16 hours a day and run a remarkably successful business. And, yes, he really did drink all that whiskey and smoke all those cigarettes. He really was a strategic genius, an incredible lawyer, and a better lobbyist and politician than many people knew. In a parallel universe where Rollin King decided to open a restaurant instead of starting an airline, New Jersey-born Herb would have been a lawyer who eventually became governor of Texas. I’m sure of that.
Instead, he was a lawyer who kept a little airline in business, winning countless court cases before taking over as CEO and growing that little airline into a giant that changed the industry. The way most of us fly today is Herb’s way. If you don’t know about all that already, you could listen to this podcast that I wrote last year.
See? Even today, Herb is influencing my career. I regret that I never did properly thank him for that, never did tell him that I wouldn’t be where I am today — better suited, albeit still sweaty — without him. Of course, tens of thousands of Southwest Employees can say something similar, whether or not they ever met Herb. And, at this moment, the thousands of people in the concourses of Love Field could also say something similar, if only they knew that they, too, wouldn’t be where they are right now without Herb. The cities of Dallas and Fort Worth once sued Southwest — repeatedly — trying to force the carrier to move to DFW Airport. Back in those olden times, the cities wanted to shutter Love Field. Without the shrewd legal moves made by Herb (he was Southwest’s lawyer for years, before he officially joined the company), Love would have been shuttered, bulldozed, and paved over. Instead, when you drive into and out of bustling Love Field today, you do so along Herb Kelleher Way.
I flew into Love a couple weeks ago and took a picture of that Herb Kelleher Way street sign and texted it to my wife. She still allows me to display the award I received for that first story about Herb, even though it’s old and patinated and silly. She also sat with me last night, after I’d learned that Herb had died and was opening the Wild Turkey I keep in the house as an homage to him. We went through the many notes and letters Herb sent me over the years (here’s one). He always thanked me for stories I wrote about him, but the one he loved the most wasn’t about him at all. It was about Colleen Barrett, the woman who started as Herb’s legal secretary and eventually became Southwest’s chief operating officer. He mentioned that story to me every time I saw him. He was so proud of Colleen’s accomplishments and made sure people knew Southwest wouldn’t be where it was without her.
I interviewed Colleen last year for a story, and she talked about Herb in the past tense, which worried me. But I didn’t ask how he was doing. Another regret. I hadn’t seen Herb in years. But a friend of mine saw him give a speech in Houston and spoke with him afterward. She mentioned my name, and Herb told her, “You know, he’s one of my favorite people.” Maybe it was just a line, a thing he’d say about any random person. But who cares? It was awesome to hear.
That friend worked with me when I was a boss at a small Dallas media company. There, I tried to emulate Herb, to incorporate into my work his ethos about treating your people well and trusting them to take care of your customers. In the end, I was probably better at yelling than teambuilding.
In any case, I’ve always believed that one of those sons of bitches who worked for me lost the copy of The Way You Wear Your Hat, a book about Sinatra written by Bill Zehme that I had given to Herb and that he mailed back to my office after he read it. I gave him the book because I was trying to talk Herb into letting me write a book about him, about Southwest Airlines. Journalists with bigger, bolder bylines had already beaten me to that proposal. But Herb entertained a meeting with me anyway to hear my pitch about what I’d write and how we’d get it done. I brought him a gift that day, an old book I’d bought in an antiques store. I’d hollowed out its pages with an X-Acto knife and inserted a bottle of Woodford Reserve into what was left of the pages.
Woodford Reserve had, just a couple months before, claimed they’d converted Wild Turkey-swilling Herb to their brand. That wasn’t exactly true. Herb opened the book and told me, “Those bastards at Woodford Reserve gave me some of their whiskey and then decided to go out and announce that I’d changed brands, even though I haven’t. So I don’t drink their whiskey anymore.”
Nor do I.
Predictably, Herb declined to do the book with me — or, as far as I know, with anyone else. I wasn’t surprised at that, but I was surprised at why he declined. “I don’t want Southwest Airlines to come off as messianic,” he told me. “We’re not the savior of American business. We do things our way, and we do them well, and if other people can learn from that, I think that’s wonderful. But I don’t want to preach to others. I don’t want to pretend we have all the answers. We’re not perfect.”
Sure. Right. Of course. Still, I’ve always hoped that Herb was secretly writing his own Southwest tome, a book that is about everything Southwest did right and wrong, one that’s filled with smart takes on doing business and with nonsensical Herb quips like “Sometimes its better to be Irish than smart” and with wild, weird, and perhaps drunken stories about pilots and flight attendants and baggage handlers and gate agents and all those other people Herb loved. Maybe that book is now sitting somewhere in Herb’s Dallas townhouse. Maybe we’ll all get a chance to read it someday. I’ll keep a spot open on my bookshelf for it, right next to that faded award and my bottle of Wild Turkey.