OLIVER WENDELL HOLMES, JR Shortly before his second visit with her (1898), Holmes writes and signs an unromantic letter to his English lover, Lady Clare Castletown, discussing his approach to the law. Autograph Letter signed: "OWH" on verso of integral leaf, 3¾ pages, 5x8. No place, 1898 May 18.

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Condition: lightly creased, lightly soiled, otherwise fine condition
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Shortly before his second visit with her (1898), Holmes writes and signs an unromantic letter to his English lover, Lady Clare Castletown, discussing his approach to the law.
Autograph Letter signed: "OWH" on verso of integral leaf, 3¾ pages, 5x8. No place, 1898 May 18. To Lady Castletown, London, England. Begins: "My dear lady". In full: "It seems so doubtful whether this will find you still at [illegible] that I shall first remind you that I live and daily long to hear from you. I am in the midst of a consultation of a very wearing kind in which I have a long [illegible] to read and only can snatch a moment here and there when cases are called up in which I did not sit. I was disappointed with the last part of the Voyage of Consolation but the first book seems to me [illegible]. It seems much easier to begin with than to end with - so many [illegible] things begin with -- The things which you send me are always [two words illegible] & I feel a [illegible] in [2 words illegible] but do it [illegible] not in that they may arrive - [several words illegible]. My mind is like a dead jelly fish on the beach - I am afraid that yesterday I was a little sharp in my comments on my [illegible] work because I was nervous and irritable - It is a curious experience, the continuous necessity of adjustment [word crossed out] to the point of view of others & when you have strong and clear convictions - Law in general admits of such adjustments because at bottom the decision is a choice between two inconsistent desirables - and the intensity of the [illegible] desires. On the degree to which the opponent courses aim for the general good cannot be measured without precision - But when it comes to the measuring of words, in construing an instrument or a statute, theoretically some ones (sic) construction is absolutely right and anothers (sic) are wrong -- and the decision is a matter of literary tact. If others donot (sic) agree with you, the logical answer is that they do not perceive as much as you do - [illegible] always my trust in any controversy which is not the final thing to be said, and what it comes down to, is, '[illegible] I have more spiritual discernment than thou.' Dont (sic) blame me for talking law - If my pen will shape any words it is as much as I can expect. I [illegible] this will reach you on before the end of the summer. I do not talk about the war although of course -- it is constantly in one's mind. My old fellow lieutenant has gone an [two words illegible] as inspector and he is a very capable man -- but if we had a land war of any length the old fellows would give way to younger men - A general of forty five is an elderly warrior and so is a private of 30 - The young chaps have to do that business. However, Dewey is not a chicken I take it. I have rejoiced at whatever brings our two countries nearer together. I wish [illegible] would bring a [illegible] grace nearer than they promise for the moment. Good bye [illegible]. I dont (sic) feel free today much because of the doubt as to whether this reaches you." Lightly creased with folds, light diagonal crease at initials. Show through of ink. Overall, fine condition. Accompanied by unrelated autograph envelope, unsigned, 4¾x3¼, 5-cent stamp affixed, postmarked [no city] Mass., May 21, 1897. Addressed by Holmes: "To/The Lady Castletown/9 Upper Ossory/101 Eaton Place/London S.W./England". London postmark on verso. Ink note (unknown hand) at lower left margin. Lightly soiled. Torn open at upper edge. Overall, fine condition. In the year of this letter, Holmes would have his second meeting with Lady Castletown, sailing to England in June 1898, just three months before he was appointed Chief Justice of the Massachusetts Supreme Court. In this letter, Holmes mentions the Spanish-American War, which had begun the previous month, and Commodore George Dewey, who had sailed into Manila Bay on April 30 and defeated the Spanish fleet there the following day (the city would surrender on August 15, 1898). OLIVER WENDELL HOLMES, JR. (1841-1935), son of the renowned poet, was serving as a Justice of the Massachusetts State Supreme Court (1882-1902) when he wrote this letter. It was written during a period when "The Great Dissenter" spent nearly all of his time serving the court, sitting on the bench and writing decisions. By the time Holmes had been appointed Chief Justice of that bench (September 12, 1899), he had written about a thousand decisions. Holmes considered his ability "to think under fire-to think for action upon which the great interests depend" his forte. He was appointed Associate Justice of the U.S. Supreme Court by President Theodore Roosevelt in 1902, serving on the Court from 1902-1932. In the 1890s, Holmes began an affair with a married woman, LADY CLARE CASTLETOWN, to whom this letter is written. There are 102 letters from Holmes to Lady Clare in the Holmes papers at the Harvard Law School Library. Although the correspondence covered a period of 30 years, 86 letters were written in the three years from their first meeting in 1896 to the period surrounding their second meeting in 1898, the year of this letter. Holmes wrote 18 letters to Lady Castletown in 1896, 33 in 1897 and 35 in 1898, including four and a cable in June prior to his voyage. After 1898, there was a sudden drop in numbers to two for the year and then a long hiatus when no letters were sent until 1914. The letters were then resumed, but they had become more impersonal and detached. Lady Castletown died in 1925. The Holmes-Lady Castletown affair is detailed in The Grand Panjandrum: Mellow Years of Justice Holmes (University Press of America: 1988), written by former Connecticut Congressman John S. Monagan. The feelings of Holmes for Lady Castletown, so obvious in this letter, did not destroy his more than half century of marriage (1872-1929) to Fanny Bowditch (Dixwell) Holmes, who is buried beside him. Two items.

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