Back When an Endorsement Mattered

Fess Whitaker, at left with his family, rode an endorsement (or the next best thing) straight into the office of Letcher County jailer.
Photo: via University of North Carolina

Throughout this campaign season, both presidential nominees have received endorsements from a number of high-profile people.

Senator Obama is backed by the likes of Warren Buffett, Jay-Z, and former President Bill Clinton. Senator McCain, not short on famous endorsements himself, has drawn the support of Donald Trump, Hank Williams Jr., and President George W. Bush, among others, for his ticket.

Then we all heard from Colin Powell, who cast his lot with the Republican party in the 1990’s when he strongly considered a presidential bid of his own, following an exemplary career as a military general. Powell remains popular with many on both sides of the aisle despite coming under fire for his mishandling of intelligence going into Iraq earlier in the decade. But after learning that Powell is publically supporting Barack Obama for President, I couldn’t help but wonder how much these endorsements really influence voters.

Once upon a time, in my corner of rural America, endorsements mattered. Especially for Fess Whitaker.

Fess Whitaker was born in Knott County, Kentucky, just outside the city of Hindman. When Fess was six years old his father, I.D. Whitaker died, and Fess moved with his mother, Matilda, to neighboring Letcher County, where I hail from.

Fess Whitaker
Photo: via University of North Carolina

In 1898 when the Spanish-American War broke out, Whitaker enlisted in the Army that same summer. As part of company I, 4th Kentucky Volunteers, Whitaker was deployed to Cuba and discharged a year later. However, in his self-mythologizing 1918 autobiography “The History of Corporal Fess Whitaker,” he claimed that his military service hadn’t ended in 1899.

According to Whitaker, he had reenlisted in the military in the summer of 1899 and was personally selected to join Teddy Roosevelt’s elite brigade, known as the Rough Riders. Whitaker claims that while in Cuba, allegedly fighting with Roosevelt’s unit, he fought with and was wounded alongside Roosevelt himself during the battle of Santiago and maintained a friendship with Roosevelt long thereafter.

Now, history tells us that Mr. Bull Moose Party himself did the recruiting for the Rough Riders. Former Harvard football players, Pawnee Scouts, cowboys as well as personal friends Roosevelt had made in the Dakota Badlands and as a New York City Police Commissioner rounded out his band of troops.

Corporal Whitaker fell into none of those recruiting pools. Additionally, the Rough Riders were defunct by September of 1898, a year before Whitaker’s claims to have joined.

So is it possible, then, that a little known corporal from the coalfields of Eastern Kentucky somehow back doored into Roosevelt’s social circle and military unit?

I was a junior at Whitesburg High School in 2001, sitting in Rick Adams’ US History class alongside, oddly enough, Fess Whitaker’s great-grandson Chris Whitaker, when I first heard the legend of Fess.

Teddy Roosevent and his Rough Riders after taking San Juan Hill, Cuba, July 1898
Photo: via Old Picture of the Day

According to Appalachian folklore and Mr. Adams’ lecture, when the Rough Riders took San Juan Hill, Whitaker and Roosevelt were side by side. Roosevelt alledgedly turned to Whitaker and said, “Fess, when we return home I’m going to run for president and if I win, I want to put you on my cabinet.” To which Whitaker humbly replied, “Thank you, Teddy, but I really just want to be jailer of Letcher County.”

And jailer of Letcher County he would become.

In 1917, Fess Whitaker was elected to that office. According to legend, he was a fierce campaigner, going all over Letcher County and giving spirited speeches that included, of course, the story of his conversation with Teddy Roosevelt as the two ascended to victory at San Juan Hill.

Whitaker’s strategy played well with Letcher Countians of the time. Despite being a Republican, Roosevelt was a rather popular President by most accounts in the heavily Democratic Letcher County, and Whitaker’s association with him, true or not, both won the election and made Whitaker scandal-proof while in office.

Whitaker achieved national notoriety and earned the nickname “The Jailed Jailer” as a result of his two arrests while in office, the first in 1921 for participating in a street fight, and the second in 1922 for possession and transportation of whiskey with intent to sell — during the infant years of Prohibition.

While Whitaker’s career as a Rough Rider and his friendship with Teddy Roosevelt were most likely tall tales, in fairness to Whitaker, his claims were never debunked.

On September 19, 1927, almost a year after a failed bid for Congress (he was narrowly defeated), Whitaker died in a car accident. His obituary showed up in the September 20, 1927 edition of The New York Times. Its first two lines are a final endorsement:

“Fess Whitaker, 50, Rough Rider during the Spanish-American War, Friend of Theodore Roosevelt, and figure in Kentucky was killed yesterday….“

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