The day before the tollbooth closed forever, the collector called Cowboy stood in his bright blue perch, welcoming all to “The Fabulous Florida Keys.”
For 25 years, Cowboy — or, as his paycheck called him, Ken Murray — had worked the booth on Card Sound Road, asking passing drivers for the fare with a “g’mornin’” and “thanks, boss.’’ He had learned the commuters’ names and asked after their spouses and kids. He had watched some of those kids grow up from the backseat and become drivers themselves.
The county was getting rid of his job Thursday, but Cowboy, 59, had no intention of changing his morning routine. When he started his last shift at 5:30 a.m., he was wearing a lime green dashiki and his signature straw hat, ready to greet the 1,500-odd drivers who would wind past his booth during the morning commute.
"I always said they’d have to throw me out of here, and they’re doing it," said Cowboy, as he took in cash and toll tickets. “I’m going to miss all my people. It’s been rough leading up to this day.”
On Friday, Monroe County will begin switching its last manned tollbooth to SunPass and toll-by-plate cameras. The two-person concrete tollbooth, which has been operating since 1969, and two adjacent sheds will be torn down to make room for the new machines, which will begin collecting an increased fare March 9. No tolls will be charged during the switch.
The exact fare has not yet been determined, and Monroe County officials expect there will be a discount for regular commuters between the mainland and the Keys.
But for Cowboy and the eight other full- or part-time employees who operate the 24/7 toll, the automated system won’t be the same as a smiling face taking a dollar each way to Key Largo or Miami.
"We take the time and we do say thank you, and we welcome [drivers] when they do show up," said Don Crouch, the Card Sound Toll Authority’s operations superintendent. "That’s what makes it hard for people to give it up."
Cowboy didn’t intend to become a toll collector. He didn’t have a car, house or job when he moved with his family from Connecticut in 1991.
But when he started working nights in February 1992, he found the work quickly agreed with him. It didn’t matter that the traffic in the early morning hours could be sporadic, or that Hurricane Andrew forced him and his family to take shelter at a co-worker’s home in Homestead just seven months after he started working at the booth.
He liked greeting people and getting to know them. When he was widowed three years later, the night schedule meant he could raise his two young kids during the day.
Nor was he the first to find a calling as a toll collector. When the Card Sound tollbooth opened in July 1969 — charging 25 cents — manned tollbooths dotted the state.
But Card Sound was special. Tourists passing through said it was the friendliest toll booth in the country, Crouch recalled. The collectors handed out candy to kids at Easter and kept dog biscuits on the counter for traveling pets.
Cowboy found love at the toll booth — twice. He met his second wife, Erica, when she gave him her phone number one day with her fare. When she died in 2007 of pancreatic cancer, the regular commuters grieved with him. Then in 2010, after three years of passing by, a red-headed beauty named Patti told him she was interested in a date. He asked her out that night, and four years later, they married.
After the couple moved to a farm in Redland in 2010, Cowboy began to bring jars of homemade mango and starfruit habanero marmalade to some of his regulars.
But it wasn’t always easy to work the toll, said Claude Ceilen, as he manned the side of the booth heading to Miami Thursday. Irate drivers stuck on the two-lane road sometimes took it out on them. There were two robberies in 1990. And the traffic has sometimes gotten so bad in recent years that they suspended collecting the toll for hours.
But the good moments — "the smiles, the friendly people who make you laugh" — made it all worth it, added Ceilen, 64. As one customer drove by blasting Aerosmith — a cheeky nod to a tattoo on Cowboy’s right wrist — both laughed.
"This is one of the highlights of my day," Ceilen mused. "I’ll have good memories of this place."
The Card Sound tollbooth survived robberies, crashes and even hurricanes — but it couldn’t survive time.
The Miami-Dade Expressway Authority eliminated its toll collectors in 2014, when it finished a four-year project to automate its 16 toll plazas. Both the Venetian and Rickenbacker causeways were automated the same year. The Florida Department of Transportation says it still operates about 150 manned toll lanes across the Turnpike system and other roadways, but has plans to convert them to electronic tolling in the years to come.
Last fall, Monroe County commissioners approved a design plan to convert the Card Sound tollbooth to SunPass.
The booth was supposed to close July 31, but got a reprieve when Florida Power & Light said it needed another 31 days to relocate its power lines on the right of way.
The additional month gave Cowboy, Ceilen and some of the other workers more time to find new jobs. One woman found a post at the Ocean Reef Club. Another, John Struckman, retired and moved to Ocala. Some, like Ceilen, were technically maintenance workers for the county and are slated to move back to those duties.
Cowboy got a job in the county’s public works department, though his start date has not been set.
On his last morning, Cowboy brought two jars of his marmalade and wore one of his signature African shirts, given to him by a customer.
"They’re so bright I don’t have to wear a safety vest," he joked.
As commuters rolled up to his side of the booth, heading toward Key Largo, Cowboy greeted each with a “mornin’” or “hello.” His favorite regulars got hugs and kisses, as well as, “I’ll miss you.”
"This is it," he told one woman as she pulled up to the window and handed him a toll ticket.
"Who am I going to talk to in the mornings now?" she asked.
"Your husband," he deadpanned.
Several asked for photos of Cowboy standing in the booth, barely wide enough for three adults to stand shoulder-to-shoulder. “It’s going to be demolished, all of this history here,” he said.
After his last shift ended at 1:30 p.m., Cowboy trudged over to Alabama Jack’s, the open-air biker bar that remains the only other landmark for miles on Card Sound Road.
He had told a few of his customers that he planned to grab a drink there that afternoon after his last shift, and several joined him when he arrived.
Terri Silver, who lives in Homestead and commutes to Ocean Reef for her property management business, came with her husband George, who makes a similar commute as a plumber. For 14 years, she said, Cowboy has been a fixture in her life even though she didn’t know his full name. She called him “Sunshine.” He called her “Freckles.”
“It’s a sad day," she said. The toll booth "is why a lot of people go down this road — you actually get to talk to somebody."
George Silversaid Cowboy never failed to ask after him or share photos of his grandkids. "I don’t mind taking a minute to get through there to have something good in my day."
But, he said, “the machines have officially taken over.”
Until the new machines are installed, commuters on Card Sound Road will not have to pay a toll. But drivers can expect construction delays in the meantime — and higher fares once SunPass starts working.
Cowboy said he will likely take the U.S. 1 route south when he first starts his new job in the Keys. After the new machines are installed, he expects he will commute down Card Sound Road again, paying a daily fare to the machines who replaced him. But he doesn’t plan to forget his presence there, he said.
“After this is all done and they switch to SunPass, I’m going to come down here and hide a cowboy hat,” he joked. “The ghost of Ken lives on.”