The recent news that the Winchester Sun building had been sold brought back a slew of memories about the building itself and a lengthy career carrying newspapers in Winchester. Of course, many of us will watch to see what becomes of an iconic building which has served as the hub of a local newspaper for several generations.
In the early 1950s, a youngster looking for odd jobs to supplement income—or no income at all, since weekly allowances were somewhat of a rarity then—could be a daunting task. Unlike today, there were no fast-food establishments offering opportunities for youthful employment.
My first “job” which actually produced a wage of sorts was caddying at the Winchester Country Club. I could do that at my choosing and possibly earn about $3 carrying a bag for 18 holes (at that time, it was two loops around a 9‑hole course).
There was also the occasional chance to mow someone’s lawn, although this was not a highly desirable choice because mowers were the push-type rotary and required a great deal of physical labor, for minimal recompense. Also, there were fewer homeowners in those days who didn’t mow their own lawns.
So, the most opportune chance for earning spending money came from carrying newspapers which, at that time, were mostly delivered within the city by pre-teens and teenagers walking their routes or, on occasion, riding bikes, both of which were the common means of locomotion.
My first experience at carrying papers was a short stint delivering The Winchester Sun. All the routes were taken at that time, and I just took over a route for a short period of time while the regular carrier was on vacation. I was issued a cloth bag which held all the papers for the route, given a list of the houses to receive a paper, and sent off. The route was not especially long and could be completed in a little over an hour on foot. My greatest fear was missing someone who should get a paper.
When a new bag was issued to a carrier it was always a pristine white (with the newspaper logo on it), but it quickly became soiled from the ink that transferred from the papers as they were being delivered. It was easy to spot an experienced carrier pretty quickly, by his soiled bag.
In those days, there were six papers that were regularly delivered in Winchester, The Sun, Lexington Herald (morning), Lexington Leader (afternoon), Louisville Courier-Journal (morning), Louisville Times (afternoon) and Grit. At one time or another, I carried all these papers except Grit.
Carriers got paid according to the number of papers on their route and they were required to collect from their customers—a heinous task because it was often difficult to find people at home, or a carrier had to devote part of his weekend collecting fees.
The worst experience for me was when I was carrying the Courier-Journal because it was a large paper. It usually required that batches be dropped somewhere along the route because they were just too large to be carried all at once. It was even larger on Sundays, so carrying that paper was a seven-day-a-week job.
The last paper I carried before giving up the “career” was the Lexington Herald. I lived on West College Street at the time, would get up early in the morning, walk (or occasionally ride my bike) downtown to get my papers and then start up Lexington Avenue to begin my route, which veered over to West Hickman at Burns. The remainder of my route extended west on Hickman and ended at Garner, leaving me close to home and back to bed—in the summer—for more sleep. Or getting ready for school otherwise, a process that required washing the printer’s ink from soiled hands.
I remember that my weekly pay for that route was $5.20.
In 1956 Elvis recorded “Blue Suede Shoes” and the shoes became popular with us kids. I got a pair shortly after the song came out, loafers, and wore them one morning on my route. Unfortunately, the morning dew was heavy that particular day and walking across yards left me with wet shoes and blue socks which had started out white!
We also customarily rolled the papers and bound them with rubber bands so we could toss them onto porches from the sidewalk. At one house on Garner my tossed paper broke the glass of a door sidelight. I was concerned that, it being early in the morning, the owner might think someone was trying to break in so I hurried away to complete my route.
There would be no lack of evidence as to the cause of the broken window so, knowing the lady at that house worked at the Clark County Bank (on Main Street at that time) I went to the bank later in the day to “fess up.” She was very understanding but the cost of replacing the window was a week’s pay.
A final note about The Winchester Sun. In those days, the press was located in the basement of the old building, with access for the carriers through a door on Cleveland. The door is still there, through the stone foundation. It was a dark, foreboding place, almost dungeon-like, with a small area where the carriers would wait while the papers came off the press.
A lifelong friend of mine, Jerry Linville, worked on the press, probably as his first full-time job. He worked for the Sun for fifty years, eventually becoming a sports photographer and doing other jobs before retiring.
Funny how some memories come flooding back.

