‘Bob the Mailman’ Killen retires March 31 after delivering mail in Key West for 28 years and coordinating the annual Letter Carrier Food Drive for 26 years. MANDY MILES/Keys Weekly

Bob Killen knows Key West. He knows directions, addresses, secret parking spots, current residents and who used to live where. He knows which magazines we read, how many Christmas cards we get, when our electric bill is late and how often we order stuff from Amazon.

Killen is Google Maps, the old white pages and a neighborhood watchman all rolled into a friendly smile that holds a permanent position beneath his salt-and-pepper mustache. 

The smile that’s greeted customers on his Key West mail route for 28 years has been hidden behind a U.S. Postal Service mask for the past year, but everyone knows it’s there, just as they know when Killen is in their neighborhood.

His midtown mail route — Route 10 —  takes him through a combination of residential and commercial mailboxes from White Street to George Allen apartments, and from the National Weather Service building to Truman Avenue.

Killen honks a large black horn, the kind used by birthday clowns, to alert White Street businesses of his approach and remind them to get their outgoing mail ready.

“And when I park my truck near Bayview Park, I blow my whistle,” he said. “The residents, mostly retirees, all happily come to their front gates to get their mail.”

The end of an era

But things are about to change on Route 10, which Killen affectionately calls “the ponderosa.”

Killen is hanging up his mailbag and retiring after 28 years with the U.S. Postal Service, all of them in Key West and 25 of them delivering to Route 10.

Killen will deliver his final Amazon package and birthday card on March 31.

“I’m 68 and my wife needs me,” he said. “It’s finally her turn to spend some time with Bob the Mailman.”

Killen said he’s loved the job and it’s a bittersweet ending.

“When I started this job, I was No. 64 in terms in seniority. Now I’m No. 3,” he said. 

“When I first started, it was rare to deliver any packages. Now everything is Amazon,” he said, opening the back of his mail truck, stacked floor to roof with boxes and envelopes, and recalling how much Key West has changed since he first arrived in 1973 after a Navy stint in Vietnam aboard an aircraft carrier. 

“After Vietnam, I was restationed in Key West,” he said.

The weather here was much more agreeable than in his native Detroit, and Killen hasn’t lived anywhere else since.

“Shortly after arriving, I met a girl here in Key West,” he said, referring to his wife of 41 years, Addie Killen. “It turned out she was from two towns over from me in Michigan.”

The pair operated a commercial cleaning business, Killens’ Klean-Up, for 18 years, cleaning bars, restaurants and other businesses.

“But when our first child, Robert II, came along, I lost my best cleaner, my wife. So I used my Navy service record to get a federal job with the postal service.” 

That was 28 years, countless magazines and plenty of stories ago.

Nine years after their son was born, Bob and Addie Killen welcomed a daughter, Krystal, to their clan.

Stamping out hunger

Killen was the first mail carrier to get the Florida Keys involved in the annual Stamp Out Hunger National Letter Carriers Food Drive.  During the nationwide, one-day food drive, mail carriers collect donations of nonperishable food items from homes and businesses along their mail routes. 

The event was postponed until November this year — after Killen’s retirement.

“Everything we collect here stays here, and is distributed to churches, food pantries and service agencies who help people in need,” Killen said. 

“That first year, all the food we collected fit into a single shopping cart,” he said. “In the most recent drive, we collected 22,000 pounds of food for people in the Keys. Our carriers really get into it. It’s a tough, heavy day for all of us, but we all like to see who collects the most from their folks.”

Sadly, mail carriers often see the effects of hunger and poverty firsthand as they deliver to deteriorating homes and housing projects. 

“In a way, we end up doing daily welfare checks on everyone on our routes,” he said. “One elderly woman had fallen down her stairs. She’d been on the floor for two days. When I came by on a Monday, I noticed she hadn’t taken her mail or newspaper inside. If I see uncollected mail on a porch, I first knock on the door, then I ask your neighbors, then I call the police.”

Killen said he’ll absolutely miss his customers and colleagues, and the feeling is mutual.

“Seeing Bob 10 days after Hurricane Irma was a milestone that let us know we’d be OK,” said Nan Klingener, one of Killen’s customers on Eliza Street, a proud resident of Killen’s “ponderosa.”

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Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.