Jerry Whipkey, right, made plenty of friends on the route, including Joe Marion
Photo provided
Jerry Whipkey, right, made plenty of friends on the route, including Joe Marion Photo provided
Just before the stampede of northbound traffic was released by the US 231 stoplight, Patti Perkins hailed Jerry Whipkey from dead center of the Washington Street crosswalk. “Last thing I thought I’d see you doing is walking around downtown,” cried out the Heathcliff boutique retailer in mock surprise.
It was a seemingly unexpected greeting, considering Whipkey has walked this path before. Many times. Many, many times.
Whether it was Perkins’ willingness to start a conversation while still perilously in the crosshairs of accelerating motorists, or the smile that betrayed any actual awkwardness, it was quick measure of mail carrier Jerry Whipkey’s popularity with downtown denizens.
Retiring May 31, Whipkey brings to end a journey of a myriad steps, most of them circumnavigating downtown Crawfordsville. He started twenty-five years ago with the United States Postal Service, and was assigned the downtown loop in June of 2011.
He’s never really looked back.
“I loved what I did. My route started right here,” said the easy talking Whipkey, standing on the corner of Market and Green Streets. “It had a little bit of everything. I delivered to the core of downtown, then east through the residential neighborhoods, then north to the hospital commercial area.
“It began with what the Postal Service calls a “park and loop” route. I park the truck –– the LLV (Long Life Vehicle) –– at the head of the route, then make a full loop through downtown on foot, until I return to the vehicle and move to the next stop. Later in the route, I would have fully “mounted” deliveries directly from the LLV into mailboxes, and “dismounted” routes, where the vehicle is parked, and I make the entire stop on foot.
“It was ideal for variety.”
Along the way, Whipkey made certain that he delivered more than just the daily mail.
“I found that people do have time to chat, as long as you don’t keep them from getting their work done. I always tried to make people feel positive. Put out something good, and eventually you will get back the same.”
Whipkey is still receiving positive feedback from the people he served for so many years.
“Jerry is one of the kindest men I know,” said Nogginz salon owner Jeanne Hauck, when Whipkey stuck his head in to say hello. “Really, he’s more than that. He’s just a gentle soul.
“We are going to have to get used to not seeing him in his uniform every day.”
For his part, Whipkey recalled fondly the days when Hauck’s dog, Everett, was a fixture in the salon. Their bond quickly nullified the stereotypical mailman versus dog rivalry.
“I actually learned a lot from Everett. If I came in tense or rushed, I’d take the time to pet him, and immediately I was less anxious for the rest of the day.”
It is that participation in Crawfordsville’s daily life that endears Whipkey to his beneficiaries, and is creating a jumble of emotion upon his departure. “He just always brightens our day,” said Marka McKeown of Henthorn, Harris, and Weliever P.C., in a sentiment echoed by her colleague Rachel Black.
“We sent happy cards to him, wishing him a great retirement. But really we are missing him already.”
“It always comes as a bit of a surprise to me,” said Whipkey, responding to the admiration. “Mail carriers always rank high on the list of most loved professions — right up there with barbers, teachers, and nurses. And yet, we are the ones who always bring your bills!”
Surprisingly, Whipkey wasn’t always fond of the company of unfamiliar people. “I was a terrible introvert. Early on, however, I subscribed to [motivator] Dale Carnegie’s principles: Be Genuinely Interested in People, and Be a Good Listener, for example. That’s served me.
“I do think people in small towns are more likely to want to have a conversation.”
If the way he treats the people on his route hasn’t changed much during his tenure, Whipkey knows the mail itself surely has. “We used to have our satchels full of “flats” (e.g.: Catalogs). First Class letters are no more –– all moved over to the Internet. On the other hand, our Package deliveries are way up.
“We have contracts now with FedEx and UPS to deliver what we call the ‘Last Mile’. They fly some of our packages, and we deliver some of theirs to the front door.”
More packages makes managing the carrier’s route an even higher priority. “Maximizing the time is by far the greatest pressure we face. There is just no chance to make it up anymore.”
That’s a lesson that Whipkey’s replacement on the route, Charles Allison, is learning. He’s also discovering he has some very large shoes to fill. “I’m getting to know people, but mostly they just tell me to slow down, because I’m making Jerry look bad,” he quipped.
Joking aside, Whipkey points out that all isn’t alway rosy on the route. Injuries must be worked through, and with more packages being delivered, sometimes multiple trips to the same address often occur, meaning the pressure is on to stay on time.
Dealing with the coronavirus pandemic meant encountering closed businesses and odd working hours, but surprisingly did not generate the fearfulness that Whipkey and the Postal Service anticipated. After the first couple of weeks of trepidation, Whipkey and his customers adapted to the crisis. New mailboxes were set up outside, or mail was just held at the post office for pickup.
“Now if you want real fear,” said Whipkey, “try making your deliveries in an electrical storm!”
Two pairs of quality footwear were always essential on the job. “If one pair of shoes got wet, you had a backup to keep your feet dry,” said the postman, whose slender, fit frame testifies to years on the beat. “A good pair could last you a year.”
“Watching the weather is also one of those things I’m going to miss a little bit,” Whipkey added. “I used to check the weather hourly to see what to expect next, but now there’s no challenge. If the weather is bad, I just don’t go out.”
Originally from South Bend, Whipkey attended Manchester College (now Manchester University), and was active duty for eight years in the Navy Reserves, including two Western Pacific tours aboard the Marine transport ship USS Duluth.
“Being in the Navy is part of the reason I can retire a little bit early.”
A first marriage brought him to Crawfordsville, but Whipkey found little reason to leave. “It’s a great place to raise kids. I enjoy running into people I know, and having a chat. It’s like having a little local celebrity.”
His wife of two years, Carol, is a patient representative at the Crawfordsville Specialty Clinic, and will be joining her husband in retirement shortly. The couple share six children, and 10 grandchildren spread around the country, so road trips are already in the works.
In the meantime, Whipkey is still making stops –– nowadays at the grocery, and running errands around town.
“I have always sought the simple life,” said Whipkey. “We aren’t going to cram in all kinds of activities just to be doing something in retirement. Balance and simplicity is the goal. It’s just my style.”
An avid reader, Whipkey wants to remain active in the Friends of the Library. An occasional pickup match of chess sounds inviting, and he plans on brushing up on his trivia skills –– although Whipkey puts the image of television know-it-all, Cliff Clavin (Cheers), abruptly to rest by pointing out that his skills pale next to others in town.
Planning on honoring his many requests from his customers to stop by for a chat, Whipkey has another idea if he becomes homesick for his old route. He wants to volunteer to lead walking tours of the inner city, pointing out all of the hidden treasures Crawfordsville offers. With more than a decade stomping the downtown, Whipkey feels especially qualified for the role.
“Besides,” he said, “I know where all of the restrooms are!”

John O. Marlowe is an award-winning columnist for Sagamore News Media.