Jimmy Cook saw a lot around eastern Maine during his 36 years of driving for UPS. Credit: Linda Coan O'Kresik / BDN

In his 36 years driving for UPS, Bangor native Jimmy Cook has met every sort of dog.

Terriers and chihuahuas that yip with excitement upon his arrival. Labradors with tails that wag so hard they nearly take off into the air. Big, sweet, lumbering pups like Clover, the Bernese Mountain Dog at 44 North Coffee in Deer Isle, all of whom can smell the Beggin’ Strips dog treats Cook comes armed with every day, as soon as his truck pulls up.

Cook’s tenure with UPS came to a satisfying close earlier this month, when he retired from the company with an incredibly rare, accident-free track record. He doesn’t intend to be a stranger to Deer Isle and Stonington, where he’s delivered for the past 11 years, however. As a naturally warm, outgoing and funny guy, he’s made too many friends — human and canine alike — in the close-knit island community to say goodbye.

“Jimmy could run our coffee shop by this point. He’s tasted every bean origin we’ve roasted during his 1,000-plus coffee breaks in our cafe and can brew a pour-over like a pro,” said Melissa Raftery, who owns 44 North with Megan Wood. “We already miss his 11:15 a.m. daily pull up, but have a feeling he won’t be a stranger to Deer Isle.”

Jimmy Cook, enjoying a coffee break at 44 North in Deer Isle, accompanied by the owner’s dog, Clover. Cook recently retired after 36 years driving for UPS. Credit: Courtesy of 44 North Coffee

Having delivered in towns and cities through Penobscot and Hancock counties since he started driving in 1986, Cook, 60, has friends all over eastern Maine. Whether in downtown Bangor or down a narrow island road in Stonington, people have come to expect an enthusiastic wave, barrage of jokes or quick check-in from Jimmy the UPS Guy.

Cook grew up in the Capehart neighborhood in Bangor, in a large, working-class Irish Catholic family. As the youngest of five, he credits his innate gregariousness and observational nature to the fact that he was the baby of the family, in what sometimes could be a rough and tumble part of town.

“I was a street kid, kind of, and I had to dodge other kids and my siblings and learn how to get away with stuff,” Cook said. “I’m always paying attention. And I know how to make people laugh.”

In college at UMaine, Cook was looking for a job he could do part-time to help pay for school, and happened across a listing for overnight shifts at the UPS hub in Brewer. After a year spent sorting packages, when a driving position became available, he snapped up the job. He didn’t realize that, at age 24, he’d found his career.

His first route was a place he was already very familiar with: the University of Maine campus, from which he’d just graduated in 1986.

“That was before a lot of those buildings had elevators, and I would carry 50-pound boxes of paper up and down stairs. My calves were massive,” Cook said.

One constant through Cook’s career at UPS has been the steady stream of cool music blasting from his truck. When he was delivering at UMaine, he’d make a point of saving WMEB 91.9 FM, the student radio station, for last, so he could deliver the near-daily shipment of CDs to the studio and chat with the DJs about what was new and cool. Eventually, he co-hosted a midday radio show called “Lunch with Jim the Delivery Driver,” playing classic ’80s alternative like the Replacements, the Smiths and Echo & and the Bunnymen.

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After the UMaine route came stints delivering in town in Orono and Veazie, Bar Harbor, Castine and Bangor. While on his Bar Harbor route, Cook, a proud union member with the International Brotherhood of Teamsters, was a part of the 1997 UPS strike, a 16-day action that saw 185,000 Teamsters effectively shut down UPS until they won a new contract. While Cook was on strike, Bar Harbor restaurateur Michael Boland invited him to temporarily bartend at his now-shuttered eatery, Rupununi.

“I really had zero experience bartending, but we figured it out,” Cook said. “And when the guys they got to try to run our routes in Bar Harbor came to deliver, I’d run outside with my sign to picket. I made more money in tips than I could count.”

During his stint delivering in Bangor in the early 1990s, he became a fixture downtown, which at that time was at an economic and cultural nadir. Cheryl Wixson, a longtime chef and purveyor of gourmet goods in eastern Maine, operated Gourmet to Go, a food shop and cafe on Central Street, where Jimmy was a near-daily presence.

“Jimmy is such an engaging fellow with a twinkle in his eye and keen sense of humor, and he was also a foodie in the making,” Wixson said. “Delivery days were a special treat for both of us as we swapped stories about different eating adventures.”

In 2011, Cook made his final route transfer, delivering in Deer Isle and Stonington. On those close-knit islands, he’s found a second family, though he still lives in Bangor year-round, and his daughter, Jensen Cook, lives in Portland. He’s intimately familiar with each winding back road on the islands and the people who live there — including Wixson, who moved her business to Stonington in 2013.

“I was delighted to cross paths again with my friend dressed in brown, this time as one of the island’s most beloved delivery drivers,” Wixson said. “Soon even our dogs welcomed a visit, delivery and special treat.”

Cook said that most UPS drivers have an unofficial code of honor they live by, to keep an eye on the properties to which they deliver. Cook has chased after runaway dogs, called the police on attempted burglaries, and one time came to the aid of a woman who had collapsed in her driveway on a below-zero day.

“It just comes with the territory,” he said. “You’re another pair of eyes on the ground.”

Cook has spent the past few months preparing for his post-UPS life. His major plans include spending the summer working part-time as the maitre’d at Aragosta at Goose Cove, the fine dining restaurant in Deer Isle owned and operated by his pal, chef Devin Finigan. At the lobster boil he threw last week in Stonington, he asked people to bring him neck ties he could wear for his new gig.

He’s also going to try his hand at standup comedy, something he’s always wanted to try but never officially did until a few years ago at an open mic. He intends to try out some of his material during Stonington’s Fourth of July celebrations, where he will serve as grand marshal of the parade.

“It’s not such a big step from the jokes I’d tell on the road,” Cook said. “I always used to just make things up as I went along, but now I’m actually writing jokes.”

He may be retired now, but the show isn’t over for Cook.

“The whole reason I loved this job is that I got to entertain people, one stop at a time,” Cook said. “I guess it just comes naturally to me. And that’s not going to change.”

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Emily Burnham

Emily Burnham is a Maine native and proud Bangorian, covering business, the arts, restaurants and the culture and history of the Bangor region.