Cigars, Whiskey, & Winning: Lessons in Leadership You Don’t Want to Miss

"Leadership Lessons from General Ulysses S. Grant by Al Kaltman: How Civil War Strategies and Wisdom Inspire Modern Success"

”The great thing about Grant….is his perfect correctness and persistency of purpose.”
—A. Lincoln

Diagnosed with terminal throat cancer in the fall of 1884, Grant was determined to document his personal Civil War experiences and recover from financial ruin to provide support for his wife Julia and their family. Despite his illness, he completed his memoirs just days before his death on July 23, 1885. He was 63 years old.

President Grant at Mount McGregor, NY, 19 July 1885. Library of Congress. https://www.loc.gov/resource/cph.3b06878/

Grant’s The Personal Memoirs of U. S. Grant, from which Al Kaltman draws in his book “Cigars, Whiskey & Winning: Leadership Lessons from General Ulysses S. Grant,” offers short snippets of Grant’s experiences, transforming them into 250 vignettes covering a wide range of topics. These short stories provide a glimpse into Grant’s extraordinary yet ordinary wisdom of character and leadership, showcasing, as Abraham Lincoln stated, “it is the dogged pertinacity of Grant that wins.”

While General Grant routinely indulged in cigars and had a history with whiskey, "Cigars, Whiskey & Winning” is firmly anchored in illustrating Grant’s practical and unassuming, and equally indispensable, leadership whose impact on the conduct and outcome of the Civil War was more so than any soldier who fought in that conflict.

Kaltman’s format is simple, easy to read, and effective. Presented in chronological installments, the vignettes cover Grant’s early years, his experiences in the Mexican-American War, and, primarily, his Civil War years. Through these snapshots, we get a glimpse of Grant as an everyday man who makes errors but learns from them, an intuitive thinker, a strategist, a humanitarian, and a driven leader. He embodies practical leadership and management principles. Kaltman closes each short story with his modern-day take on the lessons applicable to today’s business leaders and managers.

Unfortunately, history has portrayed Grant as the colorful whiskey-drinking and cigar-smoking leader of the Union military machine.  Grant is far more than these images, and this book does well in correcting those misperceptions.

Ulysses S. Grant. Brady-Handy photograph collection, Library of Congress, Prints and Photographs Division.  https://www.thenmusa.org/biographies/ulysses-s-grant/

Kaltman’s book is a page-turner revealing the deeper layers of Grant’s character, unassuming nature, and leadership on the highest stage, underscoring his strategic vision and humanitarian instincts. In it, Kaltman touches on many topics ranging from Grant’s views on:

• Seizing opportunities

• Responding to mistakes and failure

• Understanding your adversary

• Seeing and comprehending the total strategic picture in the context of battlefield actions

• Shifting paradigms by thinking anew and adapting to new circumstances

• Reading people effectively, positioning them for success, and

• Above all, doing what is right

Throughout the stories, it is clear that Grant was persistent in his focus on the enemy, and he was well aware of the cost of war, reasoning that relentless pursuit of the enemy was the shortest way to the war’s end, stating:

“While I hope and expect to defeat them, I do not know why this war should not end, as wars generally do, by the exhaustion of the strength and resources of the weaker party.”

And in writing to President Lincoln, he accepted responsibility for his role in leading the Army, which is in contrast to the view of Grant’s predecessors;

 “Should my success be less than I desire and expect, the least I can say is that the fault is not with you.”

It is there, leading from the front, that the persona of a "muddy boot" general—one who fights and wins—emerges. This is also where you find a man of humility, intellect, and exceptional leadership under the most challenging wartime conditions.

General U.S. Grant and staff, City Point, Virginia, summer 1864.   https://picryl.com/media/general-u-s-grant-and-staff-city-point-va-summer-of-1864-1

For me, reading "Cigars, Whiskey & Winning" was a great reintroduction to General Grant and it spurred me to delve deeper into him and his impact on the Republic. My curiosity led me to lectures by noted historians and, ultimately, to The Personal Memoirs of U. S. Grant, which I look forward to reading someday (it is now on my Christmas list!).

The room in the McLean House at Appomattox C.H., in which Gen. Lee surrendered to Gen. Grant. Library of Congress https://www.loc.gov/resource/pga.02091/

For years, the true greatness of Grant’s role in preserving the Union was overshadowed by the "Lost Cause" narrative, which rose to prominence and dimmed public recognition of his achievements. Kaltman’s book makes it clear that there is much to learn from General Grant, and these lessons are as relevant today to warfighters, as well as businessmen and managers. Grant’s Civil War story is a remarkable tale of leadership, with lessons that endure to this day, exceptionally captured in the pages of "Cigars, Whiskey, and Winning."

Personal Memoirs of U.S. Grant: “…I carried a cigar in my hand…In the accounts published in the papers, I was represented as smoking a cigar in the midst of the conflict; and many persons…sent me boxes of the choicest brands”.  Photo by https://www.grantcottage.org/blog/2022/12/14/champion-of-the-weed-a-study-of-the-legendary-smoking-habit-of-us-grant

The Personal Memoirs of U.S. Grant

Kaltman repeats this successful approach in his follow-up book, "The Genius of Robert E. Lee: Lessons for the Outgunned, Outnumbered, and Underfinanced," published in 2000.

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Tags: Book Reviews, Civil War