Description:

John Kennedy
Wallingford, CT, April 10, 1935
John F. Kennedy Unique Early Choate School Letter with Handwritten Postscript
TLS

A very early typed letter signed while at The Choate School. Wallingford, CT, April 10, 1935. On letterhead of The Brief of The Choate School to stockbroker Arthur Goldsmith of Redmond & Company in New York. As business manager, Kennedy solicits support for the school's yearbook in the form of renewing an ad, and mentioning his older brother Joe. Rusted paperclip impression at top right, two small chips to bottom of right margin. Overall, very good condition. 1p. 8.5" x 11". Accompanied by a PSA/DNA pre-certification from a prior auction appearance.

In part: "…I am writing to you again to ask if you and your brother would be kind enough to renew the advertisement you have placed in THE BRIEF for the past several years. I hate to ask you this favor again, as you have been so generous to Joe and myself in previous years, but as we are behind this year, I thought you would be able to help us.

I have enclosed four contract blanks and a rate card for your convenience…"

Kennedy adds in holograph: "P.S. Want to thank you for the use of your apartment the night I was in New York."

In September 1931, young JFK enrolled as a freshman at The Choate School, a private university preparatory boarding school for boys in Wallingford, Connecticut. At Choate (as in life), he followed in the footsteps of his brother Joe, Jr. who was two years ahead of him.

What he lacked in academic performance as a "C" student, Kennedy made up for in boldness, and at one point even blew up a toilet seat with firecrackers smuggled into a bathroom. He formed a group nicknamed the Muckers Club - a term used by his long-suffering headmaster to describe miscreants. The group's pranks nearly resulted in JFK's expulsion from the prestigious school.

This boldness, combined with a early knack for understanding the power of relationships, is evident in our letter in which Kennedy politely requests financial help from Goldsmith, a Harvard classmate of his father Joseph P. Kennedy, Sr., and simultaneously subtly reminds him of their families' ties. A personal touch in the form of postscript seals the deal; with this, how could Goldsmith truly refuse to help his old friend's son?

Kennedy graduated from Choate in 1935 as a mediocre 64th in a class of 112 students -- but his yearbook entry foretold his future: he was selected as the student most likely to become President.

This item comes with a Certificate from John Reznikoff, a premier authenticator for both major 3rd party authentication services, PSA and JSA (James Spence Authentications), as well as numerous auction houses.

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  • Dimensions: 8.5" x 11"
  • Medium: TLS

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June 4, 2025 10:00 AM EDT
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