During their second debate, at Freeport, Illinois, on August 27, 1858, Abraham Lincoln posed a series of four questions to Stephen A. Douglas, in response to seven that Douglas had directed at Lincoln in the previous debate. Of these, the second has become the most famous, immortalized as the “Freeport Question”: “Can the people of a United States Territory, in any lawful way, against the wish of any citizen of the United States, exclude slavery from its limits prior to the formation of a State Constitution?”1 In answering in the affirmative, Douglas remained true to his “great principle” of popular sovereignty, and bolstered his re-election campaign in Illinois in 1858, but he also antagonized the South, where people believed that Douglas was stealing from the victory they believed they had won in the Supreme Court’s Dred Scott decision, which denied the constitutionality of any limitations on slavery in the territories.

The Freeport Question is also the center of one of the most durable myths surrounding Lincoln. Supposedly Lincoln had insisted upon asking the question, despite his advisors’ concerns that it would provide Douglas with an opportunity to mend bridges in Illinois and improve his own electoral chances. Lincoln knew this and chose to ask the question anyway. When asked afterwards about the decision, Lincoln allegedly said something to the effect that if the Freeport Question “has beaten me for Senator … his answer to it has beaten him for President, and that is the stake he is really playing for.”2 In Allen C. Guelzo’s characterization, Lincoln displayed both “a Christlike willingness to sacrifice himself for the sake of principle,” and “a supernatural prescience” regarding the future impact of the exchange.3 This thunderbolt took Douglas by surprise, caught him in a trap, and led ultimately to Lincoln’s election as President.

A primary source for this narrative is Lincoln advisor and Illinois newspaper editor Joseph Medill, who described the episode in his own paper, the Chicago Tribune, in 1895, and who claimed to have been a participant in these events.4 Medill’s recollections, however, have been analyzed and refuted by a number of historians. As early as 1909 Clark E. Carr noted that, even before Freeport, Douglas was already exasperated with Lincoln’s repeated asking of the question.5 Both Don E. Fehrenbacher and Michael Burlingame have observed that, rather than counseling caution, Lincoln’s advisors were urging him to be more aggressive with Douglas at Freeport than he had been at Ottawa the week before.6 Finally, Guelzo has meticulously dissected Medill’s timeline to demonstrate that events could not possibly have transpired as Medill recalled them.7

In the course of researching the Freeport Question for an article that was recently published in the Journal of the Illinois State Historical Society, I discovered evidence that Medill’s 1895 recollection was far from the first time he had propagated his Freeport myth. In an 1875 exchange with fellow Illinois journalist James K. Magie8 that was reprinted in the New York Times that same year, Medill recounted substantially the same story; that exchange is reproduced here as it appeared in the Times on March 21, 1875. While the 1875 exchange does not break any new ground, it does demonstrate that Medill had been retailing his Freeport narrative for decades. At the very least, it undermines any attempt to maintain that Medill committed an honest mistake brought about by the distance between the event and Medill’s 1895 recollection; Medill himself contributed to the durability of the myth.


Letter from Hon. Joseph Medill—Interesting Reminiscences of the Lincoln-Douglas Campaign of 1858

The following letter of Mr. J. K. Magie, of Springfield, Ill., to Hon. Joseph Medill, of the Chicago Tribune, with the reply which it evoked from the latter, will be read with interest by large numbers of the friends of the late President Lincoln:

Mr. Magie’s Letter Secretary’s Office, Springfield, Ill. Feb. 25, 1875

Hon. Joseph Medill:

My Dear Friend: I enclose you a copy of a likeness of Mr. Lincoln, which I am sure you will recognize.

I send this to you because you are somewhat associated with it.

I met you and Mr. Lincoln at Galesburg, Aug. 27, 1858, on your way to a political meeting at Augusta, which took place the next day. I was a delegate to the meeting, (or convention,) and we all remained over night at Randolph’s hotel, Macomb. The hotel being crowded, I roomed with you. The next morning Mr. Lincoln and I sauntered out, and this likeness was obtained, as you may read upon the back of it. Please accept the likeness and put it in your album.

Yours, truly, James K. Magie.

Mr. Medill’s Reply. Chicago Tribune, March 10, 1875

Mr. James K. Magie:

Dear Sir: I acknowledge the receipt of the photograph of “Old Abe,” taken during that memorable political campaign of 1858. It is a most excellent likeness, and vividly recalls how he looked at that time.

As you mention our meeting at Macomb, a number of incidents are thereby brought back to mind. I recollect that Mr. Lincoln told me he had been sitting for a daguerreotype picture for some “friend who would not take no for an answer.” I asked him if he had got a good one. He replied that “he had seen better pictures;” whereat we both laughed. It was a standing joke of his that there was only one homelier man in Illinois than himself, and that was his friend Archie Williams, of Quincy, who, he said, had carried the ugly man’s jackknife for twenty years without meeting a successful competitor for it, and he reckoned Archie would carry it as long as he lived, though when he died it would descend to himself, not as next of kin, but of right as the ugliest man that would then be alive in the State.

You may remember how facetiously he turned the “miscegenation” arguments of the Democrats as to the consequences that would follow the abolition of slavery, at his evening meeting in Macomb, by producing statistics of the number of mulattoes there were then in the South, which by some coincidence, just about equaled the number of Democratic voters in the South—one mulatto for each Democrat—and then he asked the audience “to form their own opinions as to who were the fathers of this numerous class of peculiar people of uncertain paternity.” With such “visible evidences of the practical workings of Democracy in the South, he thought it did not become them to howl ‘miscegenation’ at the Republicans, who were not united with the negroes by any tie of blood or kinship.” I well recollect the roars of applause which greeted these palpable hits back at his opponents.

You may remember that it was at the Freeport joint debate he put several interrogations to Douglas, which the latter answered in such a way as to please the Free-soil Democrats, and their votes in the close districts turned the scale against Lincoln and beat him. He wrote out the questions he intended to propound to Douglas while in Macomb, and showed them to me on the train on the road to Freeport. Douglas had put to him a series of questions at Ottawa, which he told me he intended to answer at their next encounter, and that he would then give the “Little Giant” a “few nuts to crack which he thought would hurt his teeth before he got done with them.” I carefully read over the questions he had prepared. He asked me what I thought of them. I replied that the second one, in my opinion, was dangerous, as it afforded his opponent an opportunity to conciliate the Free-soil Democrats without losing votes down in Egypt. And I endeavored to persuade him to omit it and substitute something else. We argued the matter for a considerable time. He partly agreed to modify it a little, but said he would sleep over it first and may be he would change it in the morning or leave it out altogether. When we reached Freeport I told two or three leading Republicans about the questions. They called upon him at his room, and he read over the proposed interrogations to them. Whatever efforts were made to induce him to change the second question proved utterly unavailing. The next day at the great meeting convened to hear the joint debate he read the questions to Douglas on the stand in just the form of words originally written. The “dangerous question” which I tried to persuade him to modify reads as follows:

“Q. 2. Can the people of the United States Territory in any lawful way, against the wish of any citizen of the United States, exclude slavery from its limits prior to the formation of a State Constitution?”

Douglas answered it very much as I feared he would—even more boldly in the affirmative than I had expected. He declared that “in his opinion, the people of a Territory could, by lawful means, exclude slavery from their midst prior to the formation of a State Constitution.” He went on to say that slavery could only be upheld by “police regulations,” and that these police regulations could only be established by the local Legislature, and if a majority of the people in a United States Territory were opposed to slavery, they would elect representatives to that body who would, by “unfriendly legislation,” effectually prevent the introduction of it into their midst, &c.

When we returned to the hotel after the meeting, he said to me: “Well, Medill, how did you like the way I hoed my row with Douglas to-day?” “Mr. Lincoln,” I replied, “before you spoke you had three chances out of four for the Senate. Now I think Douglas has three out of four. I am going back to Chicago in the morning, and will make the best fight I can for you in the Tribune, but I fear you have let Douglas steal your chance of winning.” I felt very much chargined and discouraged over the results of the day’s debate, and other Republicans were greatly chop-fallen at what seemed like a triumph for Douglas. The Democrats were in ecstacies, and in our room we could hear them hurrahing and yelling like Indians for the “Little Giant” out in the street, whom they believed had routed Lincoln and won a complete victory. The reply Lincoln made to me I shall never forget, as he looked at me with a most singular expression of countenance:

“If my question about excluding slavery from a Territory has beaten me for Senator, as you seem to think it has, his answer to it has beaten him for President, and that is really the stake he is playing for.”

The result turned out exactly as each predicted it would. The “police regulations” and “unfriendly legislation” scheme of Douglas to keep slavery out of the Territories secured his re-election as Senator, but it lost him the South, which bolted the convention at Baltimore, and rejected him at the polls en masse, and caused his disastrous defeat for President.

Lincoln had so framed his question that if Douglas answered it in the negative, such answer would most surely have beaten him at the polls, and Lincoln must have concluded in his mind that Douglas’ ambition for the Presidency was so strong as to deter him from offending the pro-slavery South by answering it in the affirmative, and that he had Douglas on the horns of a dilemma.

It was a struggle between two keen and powerful players, on the political chess-board, in which the “Little Giant” was out-generaled, and lost the great game for which he was playing—the Presidency.

Your letter and the photograph of Lincoln, as he looked in 1858, have been the suggestive cause of re-calling to mind the foregoing incidents of the great Senatorial campaign of seventeen years ago, which have lain long dormant.

Respectfully yours, J. Medill.

Joseph Medill. Letter to James K. Magie, March 10, 1875 (“Reminiscences of Abraham Lincoln”). The New York Times, March 21, 1875, p. 10.


  1. Abraham Lincoln, Second Lincoln-Douglas Debate at Freeport, Illinois, August 27, 1858, in Roy P. Basler, et al., eds., The Collected Works of Abraham Lincoln, 8 vols. (New Brunswick, N.J.: Rutgers University Press, for the Abraham Lincoln Association, 1953–55), 3:43.
  2. Joseph Medill to James K. Magie, March 10, 1875 (“Reminiscences of Abraham Lincoln”), New York Times, March 21, 1875, p. 10. A similar version of the discussion is reprinted in John Locke Scripps, The First Published Life of Abraham Lincoln (Chicago, 1860; reprinted Detroit: Cranbrook Press, 1900), 77.
  3. Allen C. Guelzo, Lincoln and Douglas: The Debates that Defined America (New York: Simon and Schuster, 2008), 161.
  4. Joseph Medill, “A Reminiscence of Lincoln,” in Edwin Erle Sparks, ed., The Lincoln-Douglas Debates of 1858 (Springfield: Illinois State Historical Library, 1908), 203–206.
  5. Clark E. Carr, Stephen A. Douglas: His Life, Public Services, Speeches, and Patriotism (Chicago: A. C. McClurg & Co., 1909), 279. See also Don E. Fehrenbacher, Prelude to Greatness: Abraham Lincoln in the 1850’s (Stanford, Cal.: Stanford University Press, 1962), 131.
  6. Fehrenbacher, Prelude to Greatness, 125–26; Michael Burlingame, Abraham Lincoln: A Life, 2 vols. (Baltimore: The Johns Hopkins University Press, 2008), 1:501.
  7. Guelzo, Lincoln and Douglas, 161.
  8. Magie’s daughter subsequently invented The Landlord’s Game, the precursor to Monopoly. Mary Pilon, “Monopoly’s Inventor: The Progressive Who Didn’t Pass ‘Go’”, New York Times, February 13, 2015, https://www.nytimes.com/2015/02/15/business/behind-monopoly-an-inventor-who-didnt-pass-go.html (accessed September 16, 2022).