This entry is part of our monthly series to highlight entries from the 20,000 letter Charles Roberts Autograph Letter Collection.

"...if friendship proceeds from folly I am content to be always a fool"

Like his contemporaries, a number of letters by John Jay are found throughout the collection in his many roles as Founding Father: member of the First Continental Congress, President of the Continental Congress in 1779, diplomat, the second Governor of New York, and the first Justice of the United States Supreme Court.  One interesting aspect of the Charles Roberts Autograph Letter Collection is how it highlights the personal correspondence of many public figures.  Jay’s letter to his friend and future law partner Robert Livingston dated July 15, 1765 is one example.

The letter is a response to a previous letter from Robert Livingston and features two main subjects.  The first continues a dialog taking place over several letters in 1765 between Jay and Livingston about the meaning of friendship.  Jay believes his definition of friendship varies significantly from the common definition.  For Jay, true friendship allows for the free exchange of ideas and constructive criticism with the goal of self-betterment, “…if friendship proceeds from folly I am content to be always a fool, if friendship be the result of weakness, I pray that I many never be otherwise than weak.”  For his contemporaries, however, friendship is a “selfish passion” where “their greatness of soul would not permit them to bestow more of their affections upon one than another, their wisdom needed no assistance … & cherished by the weakness of human nature.”  Jay seeks a friendship where

John Jay to Robert Livingston dated July 15, 1765 collection number number 748.

constructive criticism can be given without fear of reproach and pushes for Livingston to do the same, “What foible in your friend have you noted? What imprudences correct?  He certainly is not without foibles – he cannot be free from imprudence – nay he daily sees many of them himself, and many more must be obvious to your penetration.  When then proceeds your silence?”

The second briefer topic is of women and the false nature of flattery.  Livingston in a previous letter makes a distinction between gross (“that which credulity will scarcely believe”) and delicate flattery.  Jay, however, sees the delivery of all flattery as problematic, “Flattery is a kind of compliment, which our judgement tells us, the object to which it is addressed does not merit.”

A junior history seminar paper was written on this letter in 1989 and explores the historical and personal context behind Jay’s remarks.  Both the letter, the paper, and a transcript are available for view in Special Collections.