Few cities have as rich a cultural and sporting history as Detroit. From the ’80s Pistons to Bob Seger, Eminem to Miguel Cabrera, the Motor City is a rich tapestry of compelling figures, unbelievable moments, and uniquely American ingenuity.

On April 17, ESPN will premiere 30 for 30: Bad Boys, a documentary about those unforgettable Pistons teams. To celebrate, Grantland will devote an entire week, from April 11 through April 18, to the various stories of this wholly original place.

♦♦♦

I. Detroit Metropolitan Wayne County Airport

Let’s open here in 1974, with a dude named Bobby Shy playing a game of snooker on the airport’s mezzanine floor before heading over to the bathroom, dropping a dime in the coin slot to open up a stall, and doing a quick bump of cocaine off a Little Orphan Annie spoon. Let’s follow Bobby Shy as he struts over to a locker, no. 258, scans the empty hallway all the way down to the Eastern Airlines counter, opens the locker, ducks back into the men’s room with a manila envelope, and slides it under the door of the third stall, where another lowlife by the name of Leo Frank, who owns a nude modeling studio out on Woodward Avenue, is sitting on the throne waiting for it. (“Mail’s here,” Bobby Shy says, before walking out.) What’s supposed to be in the envelope is blackmail money, from a factory owner named Harry Mitchell, who cheated on his wife and got caught on film; what’s actually in the envelope is a copy of the Wall Street Journal and a sheet of letterhead with the words “BAG YOUR ASS” written on it in Magic Marker.

All right. So we see how that went. Now, just for fun, let’s go back and count the anachronisms: the snooker table, Eastern Airlines, the pay toilets, the printed newspaper, the very idea that sleazy blackmailers would consider the airport a safe place to extort a legitimate businessman. And, of course, the airport locker. There are no lockers at the Detroit airport anymore, which is a shame, not really for practical reasons, but because nobody ever used airport lockers with as much verve and creativity as Elmore Leonard did. The man was the Miles Davis of the airport locker.

The anecdote in that first paragraph is borrowed from 52 Pickup, which was Leonard’s first Detroit-based crime novel, his first step toward becoming arguably the most impactful writer in the history of a city that has been essentially told to bag its own ass more than once in recent years. That’s an archetypal Elmore Leonard hustler up above, Bobby Shy, the first in a lineage of bad guys so fascinating that he created an entirely new iteration of charismatic scuzzballs, which is one reason a 40-year-old piece of prose still feels fresh and contemporary, even as the world’s changed all around it. (Without characters like Bobby Shy, who knows where Samuel L. Jackson’s career might be?)

Leonard used other airports, and other airport lockers, in the climaxes of some of his most famous books, in the ones you know even if you aren’t the type to read Elmore Leonard novels — LAX in Get Shorty, PBI in Rum Punch — but as with everything else about him, it comes back home through DTW. It’s where his best characters were always from, even if they were off living somewhere else. It’s the airport Leonard took off from to visit friends and take meetings in Los Angeles (late in life, he’d slip a joint into his Virginia Slims pack before going through security, because what would they do, he figured, to a bearded octogenarian with kindly dark eyes and wire-rim glasses and a little something extra in his pocket?), and it’s the airport he always returned to, sometimes that same night.

Detroit: It’s the city where Leonard grew up, and it’s the city where he raised his family, and it’s the city where he died — and now that he’s gone, it’s the city where his legacy can and should forever be anchored. Without his books, the city would still have suffered the same hellish decline. But because of him, that suffering was rendered into an art form all its own.

II. Woodward Avenue

For a long time, Elmore Leonard was an obscurity, toiling in a dying genre in a foundering city, scrawling first drafts on yellow notepads from five to seven in the morning (no coffee until the first sentences were written) before laboring all day on the Chevrolet truck account at an ad agency called Campbell Ewald. For a short time in the 1980s, he became mega-famous, like, cover of Newsweek famous: profiled in GQ and The New York Times Magazine and Rolling Stone, praised by George Will, invited to Phil Donahue’s show, dubbed by Time “the Dickens of Detroit.” When he died last August, at age 87, he existed on some sliding scale between those two poles. Chances are you knew him, even if you didn’t know his name. Most of the social-media encomiums centered on the very good to great films adapted from his books (notably the ’90s trifecta of Get Shorty, Jackie Brown, and Out of Sight), or on the excellent television show Justified (which appears to have inspired yet another Leonard Hollywood revival), rather than the books themselves; or they linked to a list of his 10 rules about writing, published in the New York Times in 2001, which, while logical, always felt a little bit like a lark for a guy who seemed to relish hoisting a middle finger at the kinds of assholes who made rules about writing in the first place.

In a way, it’s a testament to Leonard’s gifts that he ever became so famous: Here was a writer who went out of his way to minimize the authorial presence in his books, who despised literary pretension of nearly every kind, who cared most about capturing the authentic voices of workaday characters, and who didn’t give a shit about categories. He didn’t give us traditional mysteries, or even traditional crime novels. He had no interest in whodunits; his plots unfolded entirely through the whims of the people he drew up on paper, putting them together in a room, trading points of view, and seeing what happened. He started out writing unconventional Westerns, and when Westerns began to die, he transitioned into crime novels that were essentially twisted Westerns, and then he kept on until the audience came to him. He loved movies, and he became the most cinematic writer in the history of his genre (maybe in any genre), so subtly great at writing dialogue and portraying tone that he made it seem facile, which is probably why multiple eager directors turned his novels into some of the crappiest movie adaptations you’ll ever see.

The good news is this: Thanks to the entertainment industry’s endless need for material, and thanks to his prolific output, Leonard’s work is ubiquitous and influential, and most likely will remain so. If there is any justice among the snoots who judge literary canons — and I assume Leonard engendered enough goodwill and enjoyment and respect during his lifetime to make it so, but who the hell knows how this stuff works? — he will be recognized as a trailblazer within the genre, at least as important a chronicler of the American experience as Dashiell Hammett and Raymond Chandler once were. But because Leonard’s later work shifted further from his hometown, because he made detours to Miami and Harlan County, Kentucky, and to New Orleans — because none of the four best-known screen versions of his novels are set in Detroit — there is a possibility that future readers might not actually affiliate Elmore Leonard with his hometown the way they probably should.

It’s an odd omission in an otherwise sterling oeuvre, though maybe not an entirely surprising one: There has never been a widely seen (and halfway decent) adaptation of an Elmore Leonard work set and shot in Detroit. This, even though it’s clear that the essence of Leonard’s work is here, on the streets of an American city that rose and fell in a precipitous arc during Leonard’s lifetime, on the streets of a city that is still seeking a route back from the dark days of the late 1960s and early 1970s, when Leonard started writing about it in the first place. He was one of the first people who got what Detroit was about in those declining years. His books cut straight through the heart of the city, both in a figurative and literal sense: Every one of his Detroit novels winds around and through Woodward Avenue, the wide boulevard that starts off downtown and takes you through blighted neighborhoods like Boston-Edison and off into the suburbs of Bloomfield Hills and Birmingham and Lathrup Village, the small patch of the metro area where Leonard spent most of his adult life.

“People would ask him, ‘Why Detroit?’” says his son Peter Leonard, who is also a crime novelist based in Detroit. “And he’d say, ‘Because I like it. Because it’s real.’ Really, if you’re writing crime fiction, you couldn’t pick a better American city.”

Let’s go back to ’74 again, to the first appearance of Bobby Shy in 52 Pickup: Here he is, boarding a Gray Line sightseeing bus — and just let that blow your mind for a minute, a sightseeing bus in Detroit — at the foot of Woodward Avenue, wearing a light-gray business suit with a .38 Colt Special in the pocket. And he kidnaps the bus, and he robs everyone on board, and he redirects the tour to the black inner city, points out the local whorehouse, the buildings still boarded up from the 1967 riots that decimated the city and precipitated the white flight to the suburbs. (Best as I can tell, this is Leonard’s only direct literary reference to the riots, even though they loom over everything.)

“Detroit’s a great big wonderful town, ain’t it, gang?” Bobby Shy says, and then along with his accomplice he scampers down an embankment and across the freeway to a waiting car, and we stay with him as the car veers past some worn-out apartment buildings and drifts out of sight.

III. Greektown

The five original crime books Leonard wrote in the ’70s, the five that established his voice and his characters — 52 Pickup, Swag, Unknown Man #89, The Switch, and City Primeval: High Noon in Detroit, dubbed “The Motor City Five” by Boston University English professor Charles Rzepka — are still some of the best things he ever did. Originally inspired by George V. Higgins’s Boston-based dialogue-poem/crime novel The Friends of Eddie Coyle, the Motor City Five are hard books, sharp books, profane books, and yet they still manage to be funny books, populated by unscrupulous villains like Bobby Shy and flawed protagonists like Harry Mitchell. They’re generally devoid of heroes; the plots are simple enough to dodge the convolution that marks some of Leonard’s later work. They’re about armed robbery and blackmail and kidnapping and alcoholism, and they’re set in an entirely alternate universe that still manages to feel entirely real. More than anything, they’re about change: The changes that overtake the characters dovetail with the changes overtaking the city. The Motor City Five are consistently harrowing and occasionally beautiful and deeply cool, which isn’t a bad way to describe Detroit itself. The Motor City Five were written before Leonard hooked up with his full-time researcher, Gregg Sutter, but there is slang and dialogue that is written entirely by feel and comes from both black and white characters and is so authentic that prisoners would sometimes write to Leonard and ask him how he knew so damned much.

“He’s describing a city that’s coming apart at the seams,” says Rzepka, who wrote a book-length appreciation of Leonard’s work, Being Cool. “He really hits his groove in the ’70s when he latches on to Detroit as a location. It’s a fascinating study of a city trying to keep up in the face of debilitating pressures.”

The beating heart of the Motor City Five is here in Greektown, at the old police headquarters at 1300 Beaubien. It looks sad and crusty and underutilized now, especially since it sits in the shadow of the brand-new Greektown Casino (even here, in one of the few Detroit neighborhoods that never sank all the way into disrepair, there are entire buildings for sale, or awaiting rescue). Back in ’78, Leonard hung out at 1300 Beaubien with the cops of the Detroit Police Homicide Section, for a Detroit News Magazine story called “Squad 7: Impressions of Murder.” There are heavies in that piece named Champ and Chico and Fat Cat, and there is humor intertwined with real and horrifying violence: The whole thing reads just like a Leonard novel, and many of the details went straight into City Primeval, a book about a showdown between a cop, Raymond Cruz, and a charismatic Oklahoma-born psychopath named Clement Mansell, who murders a corrupt judge in cold blood and then shacks up with a naive girl who lives on the 25th floor of an apartment building at 1300 Lafayette.

The tall, skinny building at 1300 Lafayette sits on the outskirts of downtown, and in Chapter 4 of City Primeval, two of the best pages of prose Leonard has ever written about his hometown are set there. You want to know what elevated Leonard’s bad guys into something more than caricatures? Here it is, in a description of Clement Mansell staring out the window and scanning the entire city, panning across the river to Windsor, to the towers of the Renaissance Center that now make up General Motors’ headquarters, to the concrete remnants of downtown, to the little pocket of Greektown (“he could almost smell the garlic”) and to the police headquarters at 1300 Beaubien and to the nearby Frank Murphy Hall of Justice (“where they had tried to nail Clement’s ass one time and failed”) — all that blight and halfhearted urban renewal witnessed through the eyes of a cold-blooded killer. It’s cold and ruthless and withering, and then the scene ends with Clement looking up at the sky and wondering if his mother might be floating out there somewhere in space.

IV. Eastern Market

The morning after I arrived in Detroit, Peter Leonard, one of Elmore’s five children, picked me up at the Greektown Casino and drove me around the city, up and down Woodward Avenue, past the Max Fisher Music Center, where he and Elmore would go to watch jazz, past the Majestic Theatre a few blocks farther north where, one night after a jazz show, Elmore smoked a joint and went to see a Grateful Dead cover band and lost himself watching the barefoot girls in peasant dresses twirl around near the stage. We wandered off onto side streets where entire blocks of houses had been razed, and through a mostly deserted Belle Isle, the park where Elmore had conjured literary mayhem once or twice, and we kept on Woodward straight out past Eight Mile and into the suburbs. Many of the neighborhoods Peter hadn’t seen himself in years, and he seemed almost as fascinated to revisit them as I was, to discover what was still here and what was gone.

Elmore — and Peter, in speaking to me, referred to his father as “Elmore,” though the older man often told friends to address him by his childhood nickname of “Dutch” — was born in New Orleans, the son of a General Motors dealership location scout, and the family bounced from city to city before settling in Detroit in 1934. And despite entreaties from Hollywood, despite the frequent visits to Florida, Elmore never left. He always wore unfashionable glasses, and he always had a beard, and, by all accounts, he used his ego only in service of his work.

Off Woodward in Birmingham, Peter pointed out Elmore’s favorite restaurant, which was being turned into a sports bar; he showed me where a place called Little Harry’s used to be, which is the spot Elmore took his kids to tell them about the facts of life after their dog got a hard-on. We drove down Cass Avenue, the strip that used to be overrun by prostitutes and drug dealers and has figured into the work of both father and son. We stopped for lunch at a deli in the Eastern Market district, a series of cavernous buildings and warehouses where Peter based the opening for his best-selling novel to date, Voices of the Dead. (It’s set in 1971, and opens with main character Harry Levin, a Holocaust survivor and scrap-metal dealer, fending off a mugging with aplomb.)

For most of his adult life, Peter Leonard worked in advertising, just as his father once had. He formed his own agency before he turned 30. And then one day, after the ad manager at Volkswagen picked up Peter’s designs and hurled them across the room, Peter went to visit his father. Elmore was wearing a Nine Inch Nails T-shirt and a pair of Birkenstocks, and he was lighting a Virginia Slims 100 — he’d had a character smoke them in a novel, and he’d gotten hooked himself, thereby permitting future biographers the beautiful irony of a hyperconcussive novelist smoking a liberated-woman’s cigarette — and he was talking excitedly about a scene he’d just written for a Western called The Hot Kid.

“I thought, This guy loves what he’s doing,” Peter says. “And I don’t love what I’m doing. He would give me his manuscripts, and they were always such a pleasure to read. Especially when I was in school, and I’d read all those other books that were so long-winded and wordy. Elmore’s work was accessible and fun and interesting.”

So Peter started writing a crime novel on a yellow notepad, just like his father did, and that novel was published as Quiver, and last month, Peter published his sixth novel, Eyes Closed Tight. They’re quite clearly modeled on Elmore’s tone (which has brought on the inevitable backlash of critical snark), and even as Peter has slowly begun to break away and develop his own voice and his own universe, he couldn’t resist one small suggestion Elmore made for Eyes Closed Tight, which is set largely at a Florida hotel: a brief mention of the hotel’s previous owner, a man named Moran, a throwback to Elmore’s 1982 novel Cat Chaser. It’s the only incident (to date) of their universes colliding.

Still, Peter knows he’s inexorably connected to Elmore. He writes on his father’s desk now, an Annie Leibovitz portrait of Elmore posing on South Beach at sunset hanging above him. He likes it that way. Sometimes father and son would do book readings together, and they would sit on the couch after dinner and talk about their writing, and sometimes Elmore would suggest a better character name or a better title, and he was almost always right. They lived a few minutes away from each other, not far from the house in Lathrup Village where Peter grew up, the house where his father wrote in the basement, surrounded by cinder-block walls. Peter would sneak down there and see the little writing desk and the balls of yellow writing paper wadded up and tossed on the concrete floor around the garbage can, and it looked a little bit like a prison, a place where Elmore fought for freedom against the constraints of genre writing.

“Elmore didn’t believe in plot,” Peter says. “His point of view was, ‘If I don’t know what’s gonna happen, how the hell is the reader gonna know?’ And what’s amazing, when you read an Elmore novel, is how easy he makes it look.”



V. Hazel Park Raceway

My favorite of the Motor City Five — probably my favorite Leonard novel of them all, at least among the 20 or 25 I’ve read so far — is the one called Swag, about a couple of swinging dudes who decide to try their hand at armed robbery. They do this based on the 10 rules laid out by a car salesman named Frank Ryan, all of which will eventually be broken. Given that Leonard himself became almost as famous for those 10 writing rules as he did his books, this feels like the setup for an elaborate 30-year-long joke on the entire writing-instruction industry.

But anyway, Swag is about Frank Ryan and Ernest (Stick) Stickley, and their get-rich-quick scheme, and the inevitable sloppiness and greed that destroys them. In fact, I tried to follow the path of Swag’s locations, but a lot of them were gone. The Athens Lounge on Monroe, where the cops used to hang out around the corner from 1300 Beaubien, is now a sports bar called Pappy’s. Most of the remnants of the ’70s Detroit that Leonard portrayed in the Motor City Five are now considered landmarks: the racetracks, a wholly uninviting topless club called the Bouzouki right there in Greektown, the dive bars with the survival instinct of cockroaches in a city where everything is for sale.

One night, Alex Leonard, Peter’s son and Elmore’s grandson, took me to the Painted Lady Lounge (formerly Lili’s) near his house in the ethnic stew of a neighborhood known as Hamtramck, a bar that figured into the climax of an ’80s Leonard-Detroit novel, Split Images. Alex works in advertising, too, but he’s also the drummer in an indie band called Protomartyr that appears to be on the cusp of success, which means he could potentially become the third generation of Leonard to abandon the ad business for his art.

The past few years, Alex has gone back and read everything Elmore ever wrote, and we spent the better part of the evening geeking out over locations, eating dinner at an age-old little jazz club where Elmore once got caught using a fake ID after he came home from World War II. We talked about the movie adaptations, good and terrible; we talked about the time Alex drove Elmore out to get a supply of his yellow writing pads at a warehouse somewhere, and then they went out for pancakes, and the waitress asked him, “Are you a famous writer?” And Elmore lapped it up. He didn’t get recognized too often outside of his suburban haunts, but he certainly didn’t mind when it happened. It takes you 20-some books to find fame — Elmore was nearly 60 when the barrage of critical praise came upon him in the mid-1980s — and you enjoy what you get.

I know the primary criticism of Leonard’s novels is that he was essentially writing the same story over and over again. But what if that story is continually honed and refined, and what if there’s an element of timelessness to it? What if, as Martin Amis once said, all of Leonard’s novels are actually “‘installments’ of one big novel”? And what if that one big novel — even when the scene shifts to another city — still captures the essence and feeling of the author’s hometown, an entire generation later?

Alex Leonard, whose band once practiced in a warehouse space next to a brothel, who lives among the Bangladeshis and Poles and Yemenis and Albanians and hipsters and African Americans in Hamtramck, still sees Elmore’s Detroit everywhere he looks. You immerse yourself in the novels and then you spend a couple of days in Detroit, and you start to see Elmore Leonard characters — you start to hear them — wherever you are. First night I stayed at the Greektown Casino hotel, I got off the elevator and some guy in a magenta-trimmed suit got on with a statuesque woman on his arm, and as the doors closed, he said to me, “Hey, what’s up, man, I’m the luckiest man in the world. You know that?”

One afternoon, I drove out to Hazel Park Raceway, a beat-down harness racing oval right off 696 and 10 Mile. I did this largely because I was in the midst of reading City Primeval, which opens with the psychopath Clement Mansell chasing a crooked judge from the racetrack through the suburban streets until he runs the judge and his mistress off the road and murders them both. It was the offseason for harness racing, so I didn’t think much would be happening, but it turned out the Shriners were holding their circus, and just as I got there, a bunch of animal-rights protesters were lining up at the front entrance, decrying the treatment of the elephants or something. And I thought, What if Clement Mansell could see this? And then I thought of the wristbands the writers on the Leonard-inspired show Justified wore, the wristbands with the acronym “WWED.” Which stood, of course, for “What Would Elmore Do?”

“One time when we did a book tour together, I found this book at Barnes & Noble, and the first line was ‘The wind howled like a beast in pain,’” Peter tells me. “So Elmore walks in, lights his cigarette, drinks his drink from his stem goblet, and I read the line, and he says, ‘Never open a book from the wind’s point of view.’ When he gave you advice on something, he wasn’t even thinking. It just came out.”

VI. Bloomfield Hills

The last house where Elmore Leonard lived, the one in Bloomfield Hills, is empty now. His possessions have been auctioned off, and the place has been sold, and the last remnants of Elmore in the room where he wrote countless late-period novels are the soot stains on the wall, above the sliding glass doors that look out at the swimming pool and the squirrels and the occasional deer. Leonard worked here from nine to six, and he’d chain-smoke and stare longingly out the window at the animals, and then he’d watch Jeopardy! while eating dinner in the kitchen. The best of his novels always juxtaposed the high and low, the urban and the suburban: The gem of his later Detroit novels is probably Freaky Deaky, which opens with a 25-year-old felon getting blown to pieces in his Boston Boulevard Tudor mansion.

Leonard’s final years weren’t always easy: He got divorced, and for the first time he stopped writing, watching daytime television instead with his girlfriend (who was three decades younger). He lost weight, and because he had always worked straight through lunch, he never carried much weight in the first place; Peter would have him come by for dinner, just to be sure he fed himself. Until 2013, Elmore drove a ’96 Volkswagen, and Peter could hear him chugging down the street, and then Elmore would walk in, do a little soft-shoe on his son’s hardwood floor. Peter would cook him Cajun meals, give him containers full of rice and beans, just to be sure Elmore had something to eat. Elmore started drinking again, just casually, a glass of wine or a beer with dinner (always out of a stem goblet), because he missed the look of red wine and he was coming up on 90 and what was the worst that could happen to an alcoholic at that age?

Eventually, he got the writing bug again: At the time of his death, he was working on a novel called Blue Dreams (not coincidentally, this is also the name of a popular strain of marijuana), about a champion bull rider named Kyle. It was based in Palm Springs, and Elmore never finished it, so we’ll probably never get to read it, but he was especially proud of a scene where Kyle professes his love to a girl, who then gets a tattoo on her abdomen that says, “Kyle was here.”

“His last piece of advice to me,” Peter says. “I tell him I’m working on Act 3 of my novel, and he says, ‘Take your time. Don’t rush. Take your time and do it right.’”

VII. The J.L. Hudson Company

But let’s pan away from the suburbs. Let’s end this thing downtown, because this is where Detroit is trying, once again, to revive itself: the baseball stadium, the football stadium, the Dan Gilbert buying spree, the return of several major businesses downtown, including Campbell Ewald, the ad agency Elmore once worked for. It wasn’t too long after Leonard quit the ad business that he wrote the pivotal scene in Swag, in which Stick and Frank and an assorted collection of lowlifes attempt a heist at the J.L. Hudson Company department store downtown. It doesn’t go as planned.

There’s no more Hudson’s these days; there’s a blockwide sunken city parking garage in its place, and across the street there’s a store that sells Detroit-themed merchandise, and on the wall there’s some kind of quote about knowing Detroit cool when you see it, which is all well and good, but it’s a line that pales in comparison to at least 50 lines about this city that Elmore wrote in his lifetime. Nobody reflected Detroit cool the way Elmore Leonard did, and no one ever will. The work endures, same way the city has.

And so the ending of Swag swings through this part of downtown and Greektown, then takes us back to the airport, back to the lockers at DTW. And it ends with the girl jetting off to Los Angeles and with our two bickering protagonists getting ditched, stuck here, grounded in this great big wonderful town, no way out even if they tried.

♦♦♦

Michael Weinreb (@MichaelWeinreb) is a writer based in San Francisco and the author of four books, including Season of Saturdays: A History of College Football in 14 Games, which will be published in August by Scribner.

Illustration by Gluekit.