Sunday, January 9, 2022

The Cowboy Wannabe: Doings of Dudley Doolittle

 

Doings of Dudley Doolittle: This is the name I will use in the sometimes hilarious, outrageous, or cynical short stories posted monthly on https://bingsbuzz.blogspot.com/

A fictitious name will be used in most of the stories. It is there to protect the identity of the guilty.

These true stories are over half a century old or more.


The Cowboy Wannabe

by John M. Grimsrud © December 2021

Dudley Doolittle was born into a real no frills hardscrabble Northwest Wisconsin farm life in the early 1940s. A psychopath from birth, his cowboy lifestyle evolved. A fiercely independent renegade outlaw was what ultimately developed. This was the Dudley Doolittle we came to know.

At the time of our first encounter we were always open to hospitality at our Billings Park home in Superior, Wisconsin, where we kept our refrigerator stocked with beer and our larder of wine and booze was forever there to travelers who ambled in. Needless to say people who are free with their booze acquire lots of fair weather friends.

Dudley Doolittle was introduced to us by his cousin, an old classmate of mine. Our hospitality must have been adequate because Dudley Doolittle became a regular drop in thirsty visitor. We soon met his lovely wife that psychopathic Dudley Doolittle tried to burn to death as she slept in her bed...she escaped!

Dudley Doolittle went from one criminal escapade to another logging tons of time in jail. He loved to brag about his outlaw life style. His cowboy lifestyle inclinations included cattle rustling.

He got caught because of his partner in crime was his brother-in-law Jack, and Jack ratted him out.

There you have a brief look at one of the many social misfits that made our lives lively with never a dull moment.

Now the rest of the story:

While Dudley Doolittle cooled his heels in jail for his capers, his psychopathic mind had the time to think of a fitting justice.

Here is what evolved: Like a patient spider weaving his web his plot was put into action using a beguiling confidence man act of heart warming family friendship. Dudley Doolittle soon had his brother-in-law Jack unconditionally trusting and eager to please.

The web was ready.

As an act of friendship Dudley Doolittle said he wanted to take Jack out on the town, and he said it would be his treat. First to the bar for a friendly libation. A shot of booze to toast their friendship. Dudley Doolittle complimented Jack on his great ability to handle his whiskey.

Dudley Doolittle proposed a wager:

He bet Jack he couldn’t drink an ounce of booze a minute for one hour. Dudley Doolittle goaded him on...after all Dudley Doolittle was paying the tab and to sweeten the deal further he promised a hundred dollars for one hour of drinking at Dudley Doolittle’s expense. This was just too good to be true. Dudley Doolittle and Jack shook hands on the wager. The clock was in motion. Dudley Doolittle’s brother-in-law had already downed his first shot and only had 59 more to go.

The bartender lined up the shots on the bar and Dudley Doolittle kept score.

Dudley Doolittle said that he was truly amazed at Jack’s ability. He made it to 45 shots before he fell off the bar stool. No problem, Dudley Doolittle picked him up off the floor, got him back on the bar stool, and a few more shots were put away before Jack finally lost consciousness.

Dudley Doolittle paid the tab, and he told the bartender that he would take good care of Jack. Dudley Doolittle took unconscious Jack home and put him in bed to sleep off the booze.

The next morning Jack was stone cold dead.

Dudley Doolittle said that he even went to the funeral to make sure Jack was truly dead.

The story of the circumstances of Jack’s death made the news. The bartender was charged and nearly went to prison.

The patient plotting spider got his long awaited justice.

Links to other stories in series:  

2. Adventures - St. Augustine

3. Keg of Beer St. Augustine

John Grimsrud's author's page on Amazon

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