Which individual from the Civil War would be the most interesting to sit down and speak with over dinner or a tasty beverage?
The Cleveland Civil War Roundtable
Copyright © 2025, All Rights Reserved
The January 2025 meeting of the Cleveland Civil War Roundtable featured the annual Dick Crews Memorial Debate. The topic for debate was the question: “Which individual from the Civil War would be the most interesting to sit down and speak with over dinner or a tasty beverage?” There are many individuals from the Civil War who would be interesting to have a conversation with, and the 2025 Dick Crews Memorial Debate examined the question of which of these individuals would be the most interesting, at least in the opinion of the debaters. Five debaters, each of whom chose a different person as the most interesting, presented arguments in support of their stance on this question. Below are the texts of those five arguments, along with moderator William Vodrey’s opening remarks.

Opening Remarks
By William F.B. Vodrey – debate moderator
We’re here tonight for the annual Dick Crews Memorial Debate, named after my longtime predecessor as moderator, Dick Crews. Dick once told me that the debate got its start as a Roundtable tradition because of the difficulty of finding speakers who were willing to travel to Cleveland in January! In moderating again tonight for, God help us all, my 21st year, I stand on the shoulders of giants, including Dick.
Daniel Sickles would be the most interesting person from the Civil War to sit down and speak with over dinner or a tasty beverage.
By John Syroney
General Sickles: Why did you advance your 3rd Corps forward on July 2, 1863?
Before I interpret General Daniel Sickles’ decision to advance, one must remember that when General Sickles was asked why he does not have a monument at Gettysburg, he stated, “The whole damn battlefield is my monument.”
Ulysses S. Grant would be the most interesting person from the Civil War to sit down and speak with over dinner or a tasty beverage.
By Emily Dickinson
Out of respect for General Grant’s reputation, I asked him to join me for a steaming hot cup of London Fog rather than the Woodford Reserve or glass of wine I might normally offer a guest. After the pleasantries were dispensed, I told him I was most interested in hearing his thoughts on how the Mexican-American War influenced his decisions during the Civil War. How did it help shape a second lieutenant (and later acting captain) into the illustrious General of the Army of the United States? The general most graciously answered my musings by splitting his experiences into two sections: first, how his experiences shaped what would become “Grant the General” and second, how they gave him insight into the men he would fight beside and against.
Thomas Francis Meagher would be the most interesting person from the Civil War to sit down and speak with over dinner or a tasty beverage.
By Terry McHale
The date is May 20, 1863. The location is Brigadier General Thomas Francis Meagher’s quarters on the Rappahannock River outside Fredericksburg, Virginia. Several of us have gathered to mark the general’s last day in command of his famed Irish Brigade – a brigade that has proven its mettle at every battle fought by the Army of the Potomac since Bull Run. Aside from myself, there are a small number of somber “well-wishers” including Colonel Patrick Kelly, who will be promoted to lead the shell of this once proud brigade, and Father William Corby, who is on leave from his teaching position at the University of Notre Dame to serve as the brigade’s chaplain.
Robert E. Lee would be the most interesting person from the Civil War to sit down and speak with over dinner or a tasty beverage.
By Jake Collens
General Lee, as you know, I am from the Cleveland Plain Dealer. I want to thank you for sitting down with me today to discuss some of your thoughts and feelings about the “late unpleasantness.” I know you have been reticent to go public in the past, and I appreciate this opportunity. I want this to be an agreeable conversation, so I have brought along buttermilk to help make things pleasant.
Patrick Cleburne would be the most interesting person from the Civil War to sit down and speak with over dinner or a tasty beverage.
By Paul Siedel
It was while working as a reporter for the Memphis Commercial Appeal that I sat down with General Patrick R. Cleburne, a division commander in the Confederate Army of Tennessee, in January of 1864. Over glasses of superb Irish whiskey, we discussed his proposal to tap the untapped resource of over one million Africans held in bondage and to offer them their freedom, if they would only take up arms and serve in the Confederate Army.

Epilogue: At the conclusion of the debate, the Roundtable members chose Emily Dickinson’s argument as the most persuasive that Ulysses S. Grant is the most interesting person from the Civil War to sit down and speak with over dinner or a tasty beverage.