As told and illustrated by Laura
The Milk Wager
Kenny and Charles were brothers who lived at the top of Billy-goat Hill on Payne Street in Louisville, Kentucky, during the Great Depression. Charles was the older of the two. Kenny admired and looked up to his older brother, who in turn looked after him.
One warm Saturday the boys were sitting on the steps in front of their home, when another boy came walking along pulling a wagon that held a large pail of milk he had just purchased. As this was in the 1930’s, people most often took their own pails to a dairy farmer or local market, then carried the filled pail home.

Although Kenny and Charles loved milk, it was not part of their daily meals. To them, milk was considered a rare and special treat. Charles, the wise older brother, saw the golden opportunity presented to him and decided to strike while the iron was hot. Charles asked the boy what was in his pail, knowing full well it was milk.
When the boy replied, Charles said, “I bet you a nickel I can drink that whole pail of milk.” A nickel was a pretty big bet for two young boys in those days, and Kenny said, “What are you doing?!” Some bantering ensued, with the boy and Kenny both saying there was no way Charles could manage to drink all of the milk. Charles assured Kenny he could and would win the bet.
Eventually, the bet was accepted and the boy handed the pail to Charles. Kenny and the boy watched, amazed, as Charles drank and drank huge gulps of the fresh milk. Kenny, the whole time, was longing for a drink of the delicious milk too.
When Charles had finally had his fill, he handed the pail back to the boy who looked down inside. The boy laughed and with a satisfied grin said, “I told you so! I knew you couldn’t drink it all. You owe me a nickel!” Charles handed over the nickel, then leaned back and patted his belly with a grin of his own.
Kenny was dumbfounded. “I can’t believe you didn’t let me have any.”
Charles responded, “If I let you have some, I wouldn’t have won the bet.”
“But you didn’t win!” said Kenny, still upset at missing out.
“But I did win,” Charles wisely replied. “Where else could I get all the milk I could drink for only a nickel?”
Kenny realized this was his first lesson in making a good wager.
For another of Kenneth’s wagering stories as recounted by Laura, click “2”