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Uber Driver Wonders if He Carried Drugs on 1,500-Mile Ride From Boston to Miami

On May 18, 2017, at 4:30 p.m., Uber driver William Thompson III received a ride request in Waltham, Massachusetts, outside Boston. Minutes later, he pulled his red 2014 Prius up to a Public Storage location. A middle-aged woman approached him.

“Is it OK?”

He recalls she was yelling and pointing at something.

“Is it OK?”

Thompson asked what she meant, and the woman replied that she and her husband needed to go on a long trip. Interpreting “long” as somewhere in Cape Cod or Providence, he says he agreed before seeing the destination on his phone.

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 First Street… in Miami Beach.

Thompson says the woman told him the estimated price was around $3,000 and claimed she was in a hurry. Explaining that her mother lived in Miami and was suffering from end-stage lupus, the passenger said her family’s doctor didn’t expect her mom to survive the weekend.

At that point, Thompson says he offered to take them to an airport, but the woman refused.

“No airplanes! No airplanes!”

Thompson tried to drive them to a train or bus station, but recalls that the woman said 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. So 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 their Uber apps. The ride had gone too far, and was promptly ended.

The woman panicked, but Thompson says he called Uber and eventually got it 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.”

The threesome continued driving, stopping only to get coffee, use the bathroom, and fill the car with gas. Thompson says he listened to audiobooks and language learning lessons to pass time, and 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 and took a picture of his wheels in the drop-off spot.

“I said, ‘I’ve gotta memorialize this,’” he tells me.

A message came through on his Uber app: “Thanks for prompt arrival!”

Then, after a meal, Thompson turned around and headed home. Before he found a place to pull over and sleep, he tallied up the miles he had driven, partially in hopes 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 drivers forum: “I lay claim to the longest Uber ride ever.”

“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 that comment. Had he been a drug mule and not even known it? Or was he really reuniting a family moments before the death of the 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 the woman gave him. 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, mentioning that the company has close relationships with law enforcement agencies across the country and works with them when issues involving passengers or drivers arise.

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 he still monitors an Uber driver forum to see if anyone else turns up with a similar story.

“Then I’ll know,” he says. “After all, that mom can only die once.”

This story is adapted from a longer version published today by Dig Boston. To read that version, click here.

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