In this first installment of a two-part series, freelance writer Charlie Cy provides an overview and window into his world working part-time as a Lyft driver in Louisville. In the second edition, Charlie will detail a specific encounter he experienced escorting a passenger, who distilled some ugly truths about our city, while en route to his home from the UofL ER.
FOR THE LAST SEVEN YEARS, my entire stint living in this weird and damned Derby City, after moving back to Kentucky from the Bronx in 2016, I’ve chauffeured my share of locals and tourists alike around town to their next destination.
Driving for Lyft, one of several side-hustles I do (or did, as you’ll discover), has provided me with the flexibility to set my own schedule, earn supplemental income and most importantly Get Out and Talk to The Natives, who I might not otherwise have interacted with, to get to know our little sports-obsessed, drug-addled, crime-ridden, real estate developer and private equity run hamlet of haves and have-nots nestled on the banks of the former Mason-Dixon Line that spawned Hunter S. Thompson and Muhammad Ali.
Of note, the lion’s share of these rides I’ve undertaken – mostly due to demand, but also my own selection bias – were spent escorting a motley crew of working-class folks to and from various low-income neighborhoods around town, particularly from the still hyper-segregated enclave of the West End. And it was this eccentric cast of characters who afforded me an intimate view of this city in a way no other demographic could and who I’ve come to romantically view, maybe too idealistically, as proletarian royalty, save for a small but memorable share of degenerates I encountered, who I’ll shed no tears over if I never see again.
Truth be told, beyond their propensity to tip well and connections to influence, I stand guilty as charged, and admittedly a touch short-sighted, for not particularly enjoying tending to the self-important egos within the professional managerial class who reside in the prefabricated suburbs and mega haciendas of the East End. Which is one of the reasons why I stuck to driving predominately in a small radius of neighborhoods circumnavigating downtown, and quit working entirely for Uber, which caters, if ever-so-slightly, to a more affluent stratum.
I spent two decades ministering to elites – as a captain, bartender and sommelier – while working in various posh and pompous, price-gouging, fine-dining restaurants from Palm Beach to San Francisco. And that was enough for one lifetime. I prefer to shoot the shit with common people, mainly because I’m common too. And because we need each other now more than ever as the billionaire class of conmen and nouveau-riche tech oligarchs take over.
With that said, regrettably, my driving days are in the rear-view mirror. On January 1, my vehicle, a 2007 gold Lexus sedan, grew too old to drive per Lyft’s policies. And although I’ve taken great care to keep my steed in mint condition, a fact corroborated by the endless compliments I continued to receive from my clientele into the new year, sixteen-years is nevertheless Lyft’s cap, and me and my baby have hit it. And moreover, I don’t plan on purchasing an upgrade because she’s still in her prime, as most Toyotas always are, and the last thing I need is another monthly bill.
In short, this is the end of the line. And therefore, I’d like to share a few words about my time on the road before my road days are completely behind me.
For some time now, I’ve stewed over the idea of creating a Substack newsletter devoted to some of the more colorful situations and personalities I’ve run across, but I never got around to it. This is my limited redress of that oversight.
I’ve witnessed a glut of batshit crazy shenanigans navigating Louisville’s mean streets. Met some remarkable Individuals. Been moved to tears listening to people down and out or on the come-up. Terrified by violent sociopaths. Dumbfounded by how piss-poor Louisville drivers are. And maddened by the sheer number of mammoth-sized and luxury-priced pickup trucks that are growling around town, often with the added bonus of being plastered with antagonistic “Don’t Tread On Me” (which is precisely what they intend to do to you) Gadsden Flags and assault rifle decals.
On this latter point, I’d like to briefly add, the VAST majority of these multi-ton trucks in this town were purchased to merely commute from point A to point Z and custom-engineered to assert dominance, monopolize the road, spew exhaust (AKA “roll coal”), intimidate other drivers (operating smaller more sensible vehicles), and to over-compensate for the owner’s own physical and/or mental deficits, rather than to tow, haul and traverse rugged terrain (the utility with which they were initially designed and the one which I have no bones to pick with from those using them accordingly). I wish we had an ounce of Europe’s or most of the Global South’s (for that matter) intelligence on this issue. But alas, we don’t.
But I digress.
During my tenure driving, I earned a perfect 5-star rating after transporting thousands of passengers. I don’t mention this to toot my own horn, but instead to showcase how I prided myself on providing a safe, efficient and hospitable service to every walk of life and when necessary, also performing the role of de facto maître d’, dispensing with pro-tips to visitors seeking guidance on points of interest. But my strongest asset was my simple knack at getting everyday folks to share their stories.
And there was a menagerie of those.
I drove hundreds of people suffering with addiction to methadone clinics in Southern Indiana, or to AA meetings at the Icehouse, or to halfway houses and homeless shelters like Wayside Christian, or to score more smack, meth and booze.
I also often drove Louisville’s elderly – my favorite clientele – to and from their Medicare-funded healthcare appointments (the majority of these rides were to JenCare, who contracts with Lyft). Upon arriving at their pickup location, I’d routinely get out, run around the car and offer my hand to assist these seasoned goldmines of history into my backseat, because they were prototypically frail or emaciated or obese or handicapped or even blind. And after stowing their wheelchairs and walkers and canes and various effects in the trunk, we’d cruise and chat lazily like old friends about how their doctors were or were not taking care of them, and about their bodies falling apart, and what it was like to have their hip replaced or a heart attack or an amputation from diabetes or how weak they felt after their chemo or dialysis treatments.
We’d laugh darkly about how aging isn’t for sissies. And they’d reminisce about the old times and the old-timers. About how many of their relatives and loved ones had died and what it’s like to live with so much death and be simultaneously surrounded by so many glowing grandchildren. They’d reiterate again and again about how things were back in their day. What it was like to live through the Jim Crow era. About the crazed and mean-spirited white people and cops they continuously faced. About how things have and haven’t changed in their own neighborhoods. How some things got better, and others got worse. Often, I’d hear: “We respected our elders” and “We lived by a code,” unlike “these kids today who have no sanctity for life,” especially now that things have “gotten so violent in our city.”
On the other hand, on various occasions, I had the opportunity to shepherd the object of their scorn, the gang affiliated juveniles and strapped drug dealers – yes, multiple people got into my vehicle armed with nine-millimeter handguns tucked in their waistbands, and I had to inform them firearms aren’t allowed in Lyft rides, but I drove them nevertheless – to various trap houses or to a studio off Winkler to cut hip hop tracks, or to the Hall of Justice for their pending court dates (I’ll not soon forget the building’s glass façade covered in red-paint palm-prints symbolizing the blood on the LMPD’s hands, smeared all over the windows the first full day of the Breonna Taylor protests).
Undoubtedly, I was most conscientious with this younger demographic, because they were, or I at least perceived them to be, the most volatile, and to be fair, the most dangerous. Nevertheless, I always treated them like fellows and probed them as I would anyone else, while remaining meek and making self-deprecating jokes. We’d inevitably get along, and I almost always gleaned some new insight into their world. Some of these jits were barely fifteen or sixteen-years-old and caught up in a vicious cycle of violence; one kid told me his own family members got him into the streets, while explaining how various territories and clans worked, and about how the pandemic produced a whole new set of crews that congealed in ad hoc ways and about how social media was instigating so much of the mayhem treated like sport or performance art and how no matter what, you can’t be perceived as soft.
I too drove their high-achieving peers to prized JCPS magnet schools that no longer bussed these bright black boys and girls beyond their resident school districts, and ferried their teachers, school administrators and parents to and from these same schools, who often surprised me with their two-sided observations about the bussing saga, among other revelations.
I heard anecdotes on multiple occasions that paralleled one another about how it was both JCPS’s fault for “manufacturing” the bussing crisis, but also, according to these insiders from the same neighborhoods where their progeny and students resided, there was a small but troubling cohort of kids who were simply poorly parented and being allowed to terrorize other kids on the bus as well as the bus drivers! And the drivers, who weren’t paid enough to deal with this abusive behavior, began to drop out, which produced one of the underlying causes of why there was a driver shortage (But it should be noted, I have no personal insight into this matter one way or the other, I’m merely regurgitating hearsay, but informed hearsay).
I picked up strippers and prostitutes getting off late night shifts, who gave color commentary about their customers, Johns, bosses and pimps, and transported countless exhausted mothers in the early morning hours to overpriced daycares to drop off their fussy children before escorting them on to their seemingly endless constellation of day jobs that often bled into night jobs.
They went to work at all hours of the day, and I drove them. First shift. Second shift. Third Shift. They did ‘em all. Often multiple shifts for multiple employers.
I drove security guards, nurses, cooks, social workers, grocery clerks, Ford assemblywomen and UPS warehouse workers.
I drove JBS slaughterhouse linemen who reeked of pig viscera away from the squealing sows and bubbling tanks of rendered fat in Butchertown, and transported other worker bees, who smelled like molasses and baking spices, leaving the Shively Ferrero cookie factory and Stitzel-Weller rickhouses across the train tracks from one another. Every other person, so it seemed, stunk of skunk weed. And the far limits of the West End, especially in summertime, consistently emitted the fumes of sewage due to city’s neglect of the drainage system in that part of town.
I drove endless proles from aching public housing units to church, to their auntie’s house, to corner stores, Dollar General, a distant Kroger, Indi’s Chicken, White Castle, laundromats, smoke shops, Derby City Casino, the Urban League and the YMCA.
I drove an unbearably large cadre of family members of victims who’d lost someone to gun violence.
Sped 80-miles-an-hour on poorly maintained local roads through red lights to get a baby – clenched up in mid-seizure – to Norton’s Children’s Hospital.
Had a fight pour into my car at the former Days Inn off I-65 (before it became the Arthur Street Hotel, whose admirable mission is to serve the homeless population).
Been exquisitely defrauded by slick conmen.
Felt The Fear drilled into my adrenal glands by three wild-eyed female gangbangers; a fright like I’ve never experienced from any male passenger; each was fresh out of prison, high on molly, busy regurgitating stories about women they’d previously stomped or were planning to ground and pound, and who were eager to hole up with their fellas for a big weekend at a fleabag motel off Preston. Each made it clear, when I tried to expedite our little “joyride,” that I wasn’t going anywhere until WE completed ALL of OUR errands THEY needed to run before I was FREE. Even though they’d not added any official paid stops. I politely obeyed and of course subsequently reported them once they were deposited at their destination.
I drove softspoken UofL football athletes to class, a vicious sheriff, a laconic celebrity chef Edward Lee from his Old Louisville flagship restaurant 610 Magnolia to his new Korean venture Nami (I’ll notate: you MUST try his ginger shaved ice dessert, served with lychee, ginger snaps, black sesame and coconut condensed milk, it’s ethereal, sui generis and atom-bombed with flavor).
I drove Brown Foreman middle management, endless bourbon tourists, loquacious pilots, a rude flight attendant – which should be an oxymoron – who I had to transport from Muhammad Ali International to the Indy airport two hours away, because her assignment got screwed up, and she was late and in the wrong departure city, and she wanted me to drive 100-miles-an-hour so she could make it on time, and huffed and moaned when I informed her I was already driving 85 miles an hour and wasn’t going to drive any faster because it’s not safe and that unlike Kentucky, Indiana is filled with speed traps. And then I slowly began to snap, which I never ever do, posing questions like an antagonistic reporter: “Who is going to pay for the ticket . . . And who is going to pay the cost of my insurance going up (which is already exorbitant with a clean bill of health) . . . And for that matter, who is going to pay for the two hours I have to spend driving back to Louisville once I drop you off?”
I drove belligerent garden variety alcoholics after last call, friendly La Bodeguita de Mimi servers, vets with PTSD going to the VA off Zorn, quirky country boys who loved to chit chat, manicured Omni and 21C hotel bartenders, done-up drag queens set to perform at Le Moo’s drag brunch and Play.
I drove a new hire Humana employee who’d previously worked in a pretrial diversion program at the downtown jail, who spoke at length about how awful the conditions of the facility were and how the guards were brutes who told her she was too empathetic for these animals.
I’ve driven a host of battered women going to or leaving the Center for Women and Families, as well as picking up and dropping off dedicated employees that work at Home of the Innocents.
I drove the peculiar street photographer Vyncex, Courier-Journal journalists who spoke at length about Gannett’s endless downsizing, local barflies and music aficionados going to see shows at Zanzibar. I drove throngs of tourists going to Bourbon and Beyond, Louder than Life and the Derby, as well as local teenyboppers blinged-out in glitter and pink tutus heading to Forecastle, and saucy sorority sisters who’d piled on top of each other in my backseat, dressed in Cards’ swag, clutching cans of beer and laughing and shouting random shit into the ether while heading to tailgate.
And I’ll never forget the mystic-pilgrim-gambler I picked up from the former Greyhound bus station, before the property was bought out by a developer and demolished (as an aside, the new Greyhound locale in a strip mall off 13th and Broadway is a shit show to navigate and chaos personified). But to the point, I transported this mysterious, soft-spoken sage in his 60s, who had distinguished albeit weathered features and was dressed in vagabond’s clothes, across the river to Caesar’s at midnight several years back.
He was headed to play blackjack, said he was affiliated with GOD, or was GOD, I can’t remember which. But even for a nihilist, atheist, cynic like me, there was a strange voodoo aura that emanated off of him that provoked one’s curiosity, as he assured me, he was going to make hundreds of thousands of dollars tonight at this casino, as he allegedly had played blackjack at other casinos all across the South—and even if he was deranged, I tended to believe him, about his pockets being full come sunrise.
There were also a several common themes and points I’d like to underscore:
- The LMPD were either nowhere to be found or all in one place.
- Driving along the river on I-64 from Portland to downtown at sunrise never gets old.
- “Be safe!” was the default salutation passengers delivered to me as they departed my vehicle. And it wasn’t spoken as a trite colloquialism or just something syrupy sweet you utter to say goodbye. They really meant: be safe!
- The other reoccurring phrase I heard over and over after welcoming passengers by their first name as they entered my vehicle, was: “Oh thank God! You speak English!” As both a Southerner and a cosmopolitan nomad and global-minded citizen, this was not something I particularly enjoyed hearing, but it was indicative of a personal truth that mattered to these passengers—they wanted to be able to communicate with the stranger driving them in their native tongue, and clearly, that was not their experience. I was the exception to the rule.
- Too many people are working two or three jobs to stay afloat.
- Too many people take their driver’s time for granted and go over the five minutes, which is an ample amount of time they are allotted to show up, once the driver arrives. If you are not ready to go, don’t book the trip until you are.
- Driving adolescents wearing black ski masks is terrifying, no matter how friendly or well-behaved the kid is.
- Lyft and Uber drivers in Louisville should organize and set up a union or create their own app because they are getting raped by these rideshare companies.
- Louisville feels like it’s both at the epicenter of the drug epidemic and the heart of the region’s treatment resources. Which likely is a Catch 22. Dozens and dozens of repeat passengers have told me how they came here from Michigan and Florida and Ohio and Tennessee to get clean. And of those dozens, I’ve spoken to multiple people who got clean and now work in the Big Rehab Industry, and who firmly believe that just as the Sackler Family and Purdue Pharma were preying on people with their opioid products, “some” of the halfway houses and rehabilitation clinics in this town are potentially opportunistically manipulating the local, state and federal government for various subsidies while taking advantage of the most vulnerable populations in the city (this is something I’d like to research further for a future in-depth exposé).
This concludes Part I of our two-part series.
Related Stories
Notes from the Road: Revelations of a Lone Louisville Lyft Driver – Part III
This article appears in Jan 17-30, 2025.