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Memories of a former paperboy in Winchester

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Estimated time to read:

4–6 minutes

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.


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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.

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