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Tippecanoe and Taylor, Too!

Updated: Jul 15, 2022

As a young captain in 1811, Zachary Taylor was afforded a chance to play a role in what would become a historic military campaign. But issues of inefficiency, suspicion, and poor luck sent him away from the struggle. In blogpost #5 of "Cherrypicking," Cameron Coyle uncovers Zachary Taylor's missed opportunity at the Battle of Tippecanoe.

Fantasy Football lineup as of December 26 - this week is for the Championship! "General Taylor Never Surrenders."

My passions aren’t limited to studying Zachary Taylor, my friends. I am also a diehard fan of professional football. (For those of you wondering, I am a Jets fan. What an unforgiving football life I’ve lived.)

Most Sundays this time of year consist of a television to watch, a chair to sit, and a remote to flip through the multitude of NFL games on the docket. Daily, my friends and I butt heads over the state of the league - whether the Giants are actually good, if Carson Wentz will find his way to Indianapolis or Pittsburgh, scratching our heads as to how Ryan bamboozled all of us through trades into stacking his fantasy football roster.

More than any other analyst or mega sports personality, I often turn to “The Herd” with Colin Cowherd for commentary on the National Football League. Without fail, I spend fifteen minutes of every weekday on YouTube, listening to his sometimes outlandish takes accented by his own personal life experience, tending to mention his two divorces way more than is comfortable. Some say that Cowherd is too crazy to be trusted, and those include virtually all my friends. In his defense, though, I appreciate that he presents his views with an abundance of real life support, and admits when he’s wrong.

One of his arguments, however, has stood out to me beyond the sports realm. January 15 found Colin incensed by the Cleveland Browns once again. He felt that their 2019 campaign was a complete failure; they didn’t take the many opportunities luck afforded them in seizing a playoff spot. So Colin went on a tirade, recounting his advice to his daughter that “the minute you get out of college, be ready to go, because you don’t know that the first company you interview with is the next Amazon or Microsoft” (“The Herd” 1/15/2020). Interesting enough. Not an obvious connection to Cleveland’s woes last year, but he made it work somewhat.

Then, around the four minute mark of the video, wisdom. “These little opportunities in life - the windows are brief. They don’t last very long” (“The Herd” 1/15/2020).

Last January, I embarked on rereading Holman Hamilton’s “Soldier of the Republic” to thoroughly annotate the text and revisit his early years of service. With Cowherd’s emphasis on opportunity in mind, and being the nerd I am, sports announcer and president formed an inseparable bond.

Zachary Taylor was “ready to go” upon entering the Army as a 23-year-old in 1808. He hadn’t attended college (which was not uncommon for those days, especially for Kentuckians), but he proved to be a rising star in the military. Lieutenant Taylor, described in these years as exhibiting “civility not unmixed with a small degree of the pompous stiffness of office” (Hamilton 35), showed a capacity for bringing out efficiency in his men and a trait for decisiveness, like when in his first year he single handedly moved the recruiting headquarters of Mason County, Kentucky, from Washington to Maysville - a small feat, but proved efficient in gaining recruits and decisive in its execution.

Governor William Henry Harrison, vicious Indian fighter and 9th President of the United States.

Fort Knox proved Taylor’s best work as a young officer. Now a captain, Zachary Taylor was tasked with restoring order to the garrison, located at Vincennes, capital of the Indiana Territory. Taylor’s predecessor had shot and killed one of his subordinates, and when Taylor arrived in July 1811 the fort “resembled anything but a place of defence,” soldiers being “extreamly [sic] in want of Clothing” (Hamilton 38). Three weeks into his assignment, however, Taylor had turned Fort Knox around. A future president, Indiana’s governor William Henry Harrison, lauded the Louisville product to the Secretary of War: “To all the qualities which are esteemed for an amiable man he appears to unite those which form a good officer” (Dyer 19).

Praise from Governor Harrison led to opportunity - an opportunity that may have changed the course of his career.

Here is a detailed map of the Old Northwest in 1811 - the forts, the engagements, the villages. The southwest corner shows Vincennes, the capital of the Indiana Territory and site of Fort Knox. The dotted line heading north from Vincennes is the route Harrison took to Prophetstown.

As Captain Taylor continued on at Fort Knox, Governor Harrison planned an expedition up the Wabash River. Harrison believed that the frontier was in danger. He believed that they would soon “have every Indian tribe in this quarter united against us” (Dyer 19). In Harrison’s mind, striking first and fierce would put an end to any perceived threat against settlers and the Army itself. He drew up marching arrangements at Vincennes into the autumn.

Captain Taylor played an important role in Governor Harrison’s arrangements. The savior of Fort Knox would “take the command of about eighty light troops which would have been all the light troops belonging to the regular” (Hamilton 38). This expedition up the Wabash would be the first real combative action of Taylor’s young career, and he slated to have “a very handsome command” in the proceeding (Dyer 19). Opportunity to prove himself in battle, to kickstart his rise to the pinnacle of the military hierarchy.

Taylor was ready to go. His head was in the proper space for the mission. He didn’t have to “find himself” backpacking in Europe. This was an important moment. But the fates intervened. Luck, an aspect critical to Colin Cowherd’s philosophy on opportunity, pushed the ambitious captain in another direction.

A dispatch from the War Department dated July 27, 1811 called Captain Taylor to Frederick, Maryland. There, a “Military Tribunal” was taking place against the highest ranking American officer and Taylor’s former commander, Brigadier General James Wilkinson (Wilkinson to Madison 10/9/1811). Wilkinson, a double-agent for the Spanish and self-serving prick, was described accurately by historian Temple Bodley: “He had considerable military talent, but used it only for his own gain” (Launius “Wednesday’s Book Review”). Now, President Madison ordered an investigation into his shady conduct, primarily over the Burr Conspiracy which brought many Americans into the Army.

General James Wilkinson - Teddy Roosevelt once wrote about him that "in all our history, there is no more despicable character."

Lieutenant Taylor had dealt with General Wilkinson in the past. In 1809, after his stint in Maysville, Kentucky, Taylor was ordered with his Seventh Regiment to New Orleans. Soldiers during this era of American history fought disease more often than men, and a blistering Southern summer on the Delta brought a surge of the invisible enemy to troops stationed in the Big Easy. To make a dire situation more deadly, however, Wilkinson moved the soldiers out into swampy terrain in Terre Aux Boeufs. Between May 1809 and March 1810, 686 soldiers died out of the roughly 2000 stationed there (Dyer 17). Taylor himself came down with diarrhea and dysentery during the horrid period. Eerie was the scene where “the protruding arms and legs of the deceased took the place of missing markers in reminding the living of the fate that might be theirs” (Hamilton 36).

Terre Aux Boeufs was a stain - more precisely a brown stain - on the young and small United States Army. As Wilkinson was questioned about his treasonous activities, it was deemed fair by the prosecution to look into any intentional wrongdoing at Terre Aux Boeufs, and hence Taylor was sent for. Taylor’s testimony, however, was probably nonconsequential in the outcome of the case. By Christmas, Wilkinson was acquitted, and Taylor was in Louisville, back in the business of recruiting.

As for Governor Harrison, his expedition turned out to be one for the history books. Outside of Prophetstown, the potential nexus of Native resistance, Harrison’s troops were attacked before dawn by a few hundred Natives led by Tenskwatawa. Two hours of fighting wore on until Harrison’s men secured a victory. The day after the battle, November 8, 1811, Harrison and American forces raided and burned Prophetstown to the ground. While the Governor was criticized for questionable tactics, the Republican press swooned at the marvelous bravery of American soldiers against the frontier “savages” and the defeat of the feared Indian Confederacy brewing in the Old Northwest. Harrison was lauded as a national hero, and carried that momentum into the White House three decades later. Other officers benefitted as well, some rising rapidly in the ranks. One, Joseph Bartholomew, would become a major general mostly as a result of his role in the Battle of Tippecanoe.

Battle of Tippecanoe, November 7, 1811. The engagement, controversial in its tactics and legacy, was the rallying cry in 1840 for William Henry Harrison: "Tippecanoe and Tyler, Too."

As Taylor read reports of Governor Harrison’s victory and heard about the promotions of his colleagues, he must have realized that a vital opportunity had been stripped from him. Tippecanoe was a turning point in the history of Taylor’s career, and it is undeniable that his path would have changed significantly were he fighting alongside Harrison on that seventh day of November. Quicker promotions, more recognition, larger commands sooner. Rather than his career be squandered mostly in insignificance, Taylor might have made general thirty years earlier.

Hindsight, though, shows it may have been for the better that Captain Taylor made the trip to Maryland. Would he have been killed at Tippecanoe? How would his admired personality of outward humility and decency have changed with heaping praise? Politically, would he have ruined his chances at the Presidency, as Winfield Scott did? A lot of room to speculate, but an intriguing rabbit hole to go down.

Of course, working at the next Microsoft or Amazon would be a dream come true. But, Colin, riches and success at a young age can also make an irreversible impact on young people, too, and not for the better.

There are other ways to prosperity. Some are hard, arduous. But those paths may still produce something great and something to be truly proud of.

“Now, let me shift gears to this….”



“Autumn 1811: The Battle of Tippecanoe (U.S. National Park Service).” National Parks Service, U.S. Department of the Interior,

“Battle of Tippecanoe Facts & Summary.” American Battlefield Trust, 9 Sept. 2019,

“Browns' Window May Already Be Closed, Colin Thinks Joe Burrow's Comparable Is Romo | NFL | THE HERD.” YouTube, YouTube, 15 Jan. 2020,

Dyer, B. Zachary Taylor. Louisiana State University Press (1946).

“Founders Online: To James Madison from James Wilkinson, 9 October 1811.” National Archives and Records Administration, National Archives and Records Administration,

Hamilton, H. Zachary Taylor: Soldier of the Republic. Easton Press (1989).

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