An Uber driver recalls a fare he drove all the way from Massachusetts to Miami and wonders, Wait a minute, what the hell was in the trunk?
“I’m experiencing the passing of a kidney stone.
“If I seem distracted, it’s because the pain is exquisite.”
William Thompson III is perched on the stool across from me at a coffee house near Boston. He orders peppermint tea (it’s for the kidney stone, he says) and looks at me seriously while waiting for his drink to cool.
“The first thing I have to tell you is that I have two jobs, and I can’t talk about one of them,” he says. “I won’t go on the record, so don’t ask me about that one.”
From his appearance Thompson seems like an ordinary white-haired Bostonian. He’s wearing nondescript jeans, a basic button-up, and a black coat.
But I quickly learn that he’s a slow cooker, a longtime driver who keeps stories simmering and is ready to share them with his customers, whether the drive is five minutes or an hour long. He spins yarns, then lassoes you in with them, taking people along for a ride on multiple levels.
Though he isn’t willing to give all of the personal details, Thompson says that he has always had dreams of sharing his wilder experiences with the world and claims that he is working on an autobiographically inspired fiction project that reflects his crazy cabbie stories. Get him talking, and he’ll gladly tell you about how he helped police in Brookline solve a robbery. Or the time when he was nearly arrested for robbing the Star Market in Fenway. Or how he once allowed a homeless woman and her child to live in his cab for several weeks.
“My autobiography or my biography would be very out there,” Thompson says. He also has one about the time he picked up a guy who had blown off a couple of his fingers with a gun. “I’m not trying to be coy, but let’s just say I’ve had a weird life. Weird things have happened to me a lot.”
He draws a line…
“If you want to go off the record, I’ll tell you all of it, but I don’t want to tease you and not tell you.”
I can’t verify all of the tales that Thompson tells, but I did everything I could to check out the crown jewel of his story collection: the one about what may have been the longest, and strangest, Uber ride of all time.
On May 18, 2017, at 4:30 pm, Thomson received a ride request in Waltham from his Uber app. Minutes later, he pulled his red 2014 Prius up to Public Storage on Lexington Street to pick up his passengers when a middle-aged woman approached him.
“Is it okay?”
He recalls that she was yelling and pointing at something.
“Is it okay?”
Thompson asked what she meant, at which point the woman said that she and her husband needed to go on a long trip. Interpreting “long” as somewhere in Cape Cod or Providence, he says that he agreed before seeing the destination.
The couple went into the storage building, and moments later emerged with five backpacks—stuffed with something, according to Thompson’s account—that they crammed into the trunk.
“To be honest, [the couple] almost looked like they were homeless,” he says. “They didn’t smell bad. They just looked poor.”
When the destination popped up on his screen, Thompson assumed it was a practical joke. For a second, he says he came close to kicking them out of the car.
The address was on 1st Street … in Miami Beach, Florida.
Thompson says the woman told him that the estimated price was around $3,000, and claimed that she was in a hurry. Explaining that her mother lived in Miami and was suffering from end-stage Lupus, the passenger said that her family’s doctor didn’t expect her mom to survive the weekend.
At this point, Thompson says he offered to take them to an airport, but that the woman refused.
“No airplanes! No airplanes!”
Thompson tried to drive them to a train or bus station, but recalls that the woman said that neither was direct enough.
“For someone who looked almost like a street person, she reacted with derision,” Thompson says. “‘Oh, the bus! I’ve taken the bus and no!’ It was too déclassé for her.”
Fortunately for the couple, Thompson’s other job is with his own “kind of secret” company, and his hours are flexible. Like that, they set out on a gallant journey, allegedly to return the woman to the side of her ailing mother… nearly 1,500 miles away.
As proof and for the keepsake nature of it, Thompson still has screenshots of the route, plus trip IDs, photos snapped at various pit stops along the way, a thank you message from the customer, and a payment from Uber.
The price tag on just one of the receipts, for the stretch between Connecticut and Florida: $2,283.93.
Her husband pulled out an iPad and asked if he could DJ.
“What kind of music do you like?”
“Dealer’s choice,” Thompson replied. “Whatever you’d like.”
The male passenger ran through his playlist until New Haven, where a message popped up on all of their Uber apps. The ride had gone too far, and was promptly ended.
The woman panicked, but Thompson says he placed a call to Uber, and after some waiting got it all sorted out. A man named Jake from the priority support team sent him a message, “As you know, trips like this are extremely uncommon and cause some minor issues in the system.”
They continued driving, stopping only to get coffee, use the bathroom, and fill the car with gas. Thompson says that he listened to audiobooks and language learning lessons to pass time, and that the couple mostly kept quiet in the back, either sleeping or using their iPads with headphones.
Once they got to the Sunshine State, though, Thompson says the husband and wife started asking to take smoke breaks.
“We probably made 12 stops going through Florida,” he recalls.
After nearly 30 hours of straight driving, they arrived at First Street in Miami Beach at around 9 o’clock on Friday night. Thompson says the couple exited the car, collected their bags from the trunk, and walked off. He then got out to stretch, took a picture of his wheels in the drop-off spot, and headed back.
“I said, ‘I’ve gotta memorialize this,’” he tells me.
A message came through on his Uber app: “Thanks for prompt arrival!”
Pics or it didn’t happen
Thompson shows me a selfie he took in a Steak ’n Shake in Miami. In the photo, his eyes are almost entirely closed. He’s holding up two fingers in a lazy peace sign, kind of like a teenager. Remembering the meal break, Thompson says there was a mixup at the counter, and that a stranger accidentally paid for his salad and shake. He thought of it as a reward for his heroic behavior, a little gift for driving all day and night to bring a woman to her dying mother’s bedside.
“Miami is my town,” he says he told the waiter. “I should stick around and soak up the magic.”
Before he found a place to pull over and sleep, Thompson tallied up the miles he had driven, partially in hopes that he had set a record. In later research, he could only find some fellow drivers bragging about measly trips from New York to Virginia, and posted about his own voyage in a forum for drivers: “I lay claim to the longest Uber ride ever: a 1600-mile trip from Waltham MA to Miami Beach FL.”
“I exaggerated [the length],” Thompson says. It’s unclear why he tacked on the extra 100 miles; none of the contenders seemed to come anywhere close to his feat.
“Pics or it didn’t happen,” one user responded.
Thompson produced screenshots and a gentlemanly retort: “Given the extreme improbability of my trip from Waltham to Miami Beach, I understand the skepticism. Here is some convincing evidence that I’ve attached.”
At which point his foil replied: “probably carried 20lbs of weed down or other various class A’s. lol.”
Thompson says he paused upon reading the comment. Had he been a drug mule and not even known it? Or was he really reuniting family moments before the death of a matriarch?
He retraced all of it—the storage facility, the bags, the airplane paranoia, the frequent smoke stops. It seemed to fit. But then again, so did the story that the woman gave to him.
“It’s like a puzzle,” Thompson says. He shakes his head. “You put it together and go, Oh, yeah! That’s cool. And then take the pieces apart and you reconfigure the pieces and put them together again and it’s an entirely different picture, and you say, ‘Wait a minute. Which is it?’”
I initially heard the Massachusetts-to-Miami story secondhand from Wendy Lewis, a recent law school graduate who was a passenger in Thompson’s Uber. He told her his tale on a ride from Waltham to Brookline, with Thompson taking the whole 30 minute haul to get through the details as he effortlessly weaved through Greater Boston traffic. Lewis lauded her driver’s ability to tell a story, but also questioned his judgment, at least in the Miami case.
“I figured it out as soon as he said that they came out with backpacks,” she said. “I was fairly certain they used him as a mule.”
Uber, however, says it’s not that simple.
“It would be foolish to assume that it was a drug run just because it was a long trip,” Susan Hendrick, an Uber communications professional, said. At the same time, Hendrick admits that enforcing this sort of thing isn’t easy.
“People could easily bring drugs on almost any form of transportation,” Hendrick added. “We’re not immune to that.”
The spokesperson also pointed to Uber’s strict policy against drug-running, even mentioning that it has close relationships with law enforcement agencies across the country and works with them when issues involving passengers or drivers arise.
If you hail enough Ubers in Boston, you might get Thompson as your driver. He will pull up in his red Prius, and he will probably tell you how his car—this very car you’re in—was part of what may have been the longest Uber ride of all time. And possibly an interstate drug deal as well.
Thompson says his friends still tease him about the run. He prefers to think of himself as a hero, but also has let his imagination roam about having a drug connection in Miami. In the scenario that plays out in his head, the kingpin asks his mules if there were any problems, and they say, No, we got this idiot. He was very diligent … He bought our dying mom scenario like that and seemed very concerned. We were lucky we got this guy.
Thompson hasn’t seen the couple since, but says that he still monitors an Uber driver forum to see if somebody else turns up with a similar story.
“Then I’ll know,” he says. “After all, that mom can only die once.”
This article was cross-published with the Miami New Times.