Excellent so far, Roger, this is correct.

Judge David Davis?

This is an outstanding guess, Roger, but, sorry, not correct.

Hint #1: I will answer yes/no questions, so, please, think of some to approach.

This could be a newspaperman or author who favored Lincoln. So I will guess Isaac Newton Arnold.

You are on the right track, Roger, but it's not Arnold either.

Josiah Holland?

Kudos, Roger, you are absolutely amazing!!!

I got the dialogue from this essential book:
https://www.amazon.com/Essential-Lincoln...B006G8373W

Roger, you win a virtual trip to Holland, precisely to Volendam near Edam which provides the setting - enjoy the "Wooden Clog Dance" from (German) Albert Lortzing's opera "Zar und Zimmermann":
https://m.youtube.com/watch?v=GUCqjhnQb9U

Thank you for such a great prize, Eva! It will bring back memories of long ago. When our daughter, Sarah, was a little girl, Vicki and I used to have family outings at Dutch Village in Michigan.

(07-09-2016 07:07 PM)Eva Elisabeth Wrote:  "Jane Swisshelm wrote that before her February 1863 visit, she had 'a feeling of scorn' for Lincoln before she met him, she was 'startled to find a chill of awe pass over me as my eyes rested upon him. It was as if I had suddenly passed a turn in a road and come into full view of the Matterhorn.' She wrote: 'I have always been sensitive to the atmosphere of those I met, but have never found that of any one impress me as did that of Mr. Lincoln, and I know no word save 'grandeur' which expresses the quality of that atmosphere. I think that to me no familiarity, no circumstance, could have made him other than grand. The jests, the sallies, with which he amused small people and covered his own greatness, were the shrubs on the mountain side, the flowers which shot up in the crevices of the rocks! They were no part of the mountain. Grandly and alone he walked his way through this life ; and the world had no honors, no emoluments, no reproaches, no shames, no punishments which he could not have borne without swerving or bias.”

[O. Oldroyd: "The Lincoln Memorial: Album-immortelles", p. 413-414]

On August 13, 2013, I made the following post to the thread “RE: President Lincoln and the Sioux Indian uprising in Minnesota in 1862” at post #13. After I read Eva’s posting tonight, I did a search on Roger’s website using my name and the search term “Swisshelm” to locate this post:

"Minnesotans denounced the President's decision. In February, the abolutionist-feminist Jane Grey Swisshelm told a Washington audience that if 'justice is not done,' whites in Minnesota 'will go to shooting Indians whenever these government pets get out from under Uncle Sam's wing [i.e., President Abraham Lincoln alone]. Our people will hunt them, shoot them, set traps for them, put out poisened bait for them -- kill them by every means we would use to exterminate panthers.'' ("Abraham Lincoln: A Life" Vol. Two, page 483.)

I then went to the source citation for the source of the quote. It was Washington correspondence [presumably, from Jane Grey Swisshelm] dated February 23, 1863 and published in the St. Cloud Democrat on March 5, 1863.

And this quotation from Professor Burlingame’s book was immediately followed in the same paragraph by another closely related story that apparently occurred after Ms. Swisshelm had become so impressed by the "Matterhorn" character of President Abraham Lincoln in February, 1863.

“When she urged Secretary of the Interior John Palmer Usher to recommend to the president that Indian prisoners be executed in retaliation for Sioux depredations in 1863, Usher replied: ‘Why it is impossible to get him to arrest and imprison one of the secesh women who are here – the wives of officers in the rebel army, and hold them as hostages for the Union women imprisoned in the South. We have tried again, and again, and cannot get him to do it. – The President will hang nobody.’”

The source citation for this latter quotation is Washington correspondence by Jane Grey Swisshelm, 1 May, St. Cloud Democrat, 14 May 1863; Swisshelm, Half a Century, 234.

Which two characters in the saga reportedly occasionally enjoyed a game of "mumble-the-peg*" together?

(*Mumble-the-peg was a very popular schoolyard game in the nineteenth and first half of the twentieth centuries, but with increased concern over child safety the game has "declined in popularity".

It is played between two people with the aid of a pocket knife. The two opponents stand opposite one another with their feet shoulder-width apart. The first player then takes the knife and throws it to "stick" in the ground as near his own foot as possible. The second player then repeats the process. Whichever player "sticks" the knife closest to his own foot wins the game. The loser of the game has to take it out with his teeth.

If a player "sticks" the knife in his own foot, he wins the game by default, although few players find this option appealing because of the possibility of bodily harm. There are many variants of the basic game.)

John Wilkes Booth and Matthew Canning?

Good guess, Roger - as a general remark I must add that there sure may have been other parties who did this, but I am looking for a party who, I know, reportedly did - but these are not the two individuals I am looking for.

Hint #1: The games took place during the CW.

Mary Lincoln and Julia Grant Edwin Stanton and William Seward?

Was one of the characters Secretary of War, Edwin Stanton, and the other man someone from his hometown of Steubenville, Ohio?