10 Fascinating Letters Worth Reading by Nelson Mandela, Eleanor Roosevelt, and More

Before the digital age, handwritten or typed letters were the only real way of communicating. While it meant waiting for days and even weeks to hear a response, they were used to convey all sorts of information from the mundane to the life-changing.

Here we look at a handful of letters from artists, writers, and historical figures to get a sense of who they were and what they were going through at the time.

Nelson Mandela’s Valentine’s Day Letter

The South African, anti-apartheid revolutionary, political leader, and philanthropist Nelson Mandela often hand-wrote letters and in 2017 it was announced the letters he wrote while in prison for fighting for a democratic and free society would be published in a book posthumously.

In this letter from 1995, Mandela responds to a young person about love and Valentine’s Day. Addressing the respondent point by point, he appears humble and reserved when talking about the language of love: “Many of today’s younger generation are independent and clear thinkers with their own set of values. It would be most presumptuous for a man of 78 to advise them on how to handle relationships.”

Eleanor Roosevelt writes to Joe Lash

In this letter from 1944, Eleanor Roosevelt wrote to her friend and long-term pen pal Joe Lash, an American radical political activist, journalist, and author who was serving in the Pacific during the Second World War. Roosevelt was still serving as First Lady to her husband Franklin D Roosevelt, and in the letter she discusses progress in the war and also her husband’s changing strategy.

“F keeps us all a bit undecided by saying he doesn’t know what he will do and that when he hears Hitler is ready to surrender he will go to England at once and then in the next breath that he may go to Honolulu and the Aleutians. He feels very well again and looks well” she writes. It’s fascinating to see the matter-of-fact language Roosevelt uses in her letter, considering she is writing about a particularly heavy subject.

JoAnne Smart’s letter to her parents

Elizabeth JoAnne Smart was one of the first two African American students admitted to the University of North Carolina at Greensboro, then known as the Woman’s College of the University of North Carolina.

The letter, written in 1957, is kept fairly brief with Smart simply detailing parts of her day to her parents, mentioning things like missing breakfast because she overslept and knowing they worry about her when she doesn’t write. Though her letters sound positive, in later life Smart wrote about her sense of social isolation when at college and the necessity of attending dances at nearby all-black schools.

Miguel de Cervantes Saavedra and Rodrigo Osorio’s agreement

This letter of written agreement between the eminent Spanish author Miguel de Cervantes Saavedra and Rodrigo Osorio was to confirm that Cervantes would compose six comedies. Written in 1592, 13 years before the publication of part one of Don Quixote, Cervantes was to be paid 50 ducats apiece by Osorio, who was a manager of sorts. The condition of the agreement was that Cervantes was to make these comedies the best in Spain. In one later correspondence between the pair, Osorio writes: “Sir I have read your play, and it simply will not do.”

Samuel Beckett’s letter to schoolboy John Hughes

In 1976, playwright Samuel Beckett, known for his works Waiting for Godot and End Game, wrote a letter to school boy John Hughes. The letter is a reply to the boy, who was living in the house where Beckett grew up in Cooldrinagh in Foxrock, Dublin.

Writing from Paris, Beckett tells the boy which schools he attended and which room he slept in in the house. He ends the letter with this final sentence: “If you ever meet my ghost in house or grounds, give it my regards. Wishing you happy years in that old home.”

Letter to Norman Rockwell from Allen Hurlburt

Art director of bi-weekly, general interest magazine Look, Allen Hurlburt, wrote this letter to artist Norman Rockwell in 1965. The letter alludes to the publication of Rockwell’s most recent painting in the magazine, Southern Justice and mentions that “everyone thinks it’s a smasher”. Rockwell’s visualizations of America became significant in the Civil Rights Movement, with his artworks often portraying the injustices that were still occurring.

A letter asking women to petition congress

Written by Elizabeth Cady Stanton, Susan B. Anthony, and Lucy Stone, this letter from 1865 urges friends to send petitions for women’s suffrage to their representatives in Congress.
Stanton was an American suffragist, social activist, abolitionist, and leading figure of the early women's rights movement. She met Anthony in 1851 and they went on to become lifelong friends and co-workers in social reform activities. The pair were influenced by Stone for her work, and was often called “the heart and soul” of women’s rights.

The letter makes a powerful start in urging women to have their voice: “As the question of suffrage is now agitating the public mind, it is the hour for Woman to make her demand”.

Letter from Martha Washington to Burwell Bassett

This rare surviving letter of Martha Washington, wife of George Washington, demonstrates how the American Revolutionary War impacted both of them, especially during the hard winter in Morristown, New Jersey in 1779. The General had created a headquarters there, for him to work on strategy and coordinate his army to stay together.

The Washingtons parted in 1780, and Martha headed home to Mount Vernon. This letter is addressed to her cousin Col. Burwell Bassett and sees her asking him whether his daughter could come and spend time with her. The letter also discusses the hard time both her and her husband had endured at Morristown. “The poor general was so unhappy that it distressed my exceedingly,” she wrote.

Letter from Mary S Peake to Simeon Jocelyn

Mary S Peake was an African American educator from northern Virginia and became the first teacher for the freedmen at Fort Munroe in 1861. Though having previously worked as a dressmaker, she had dedicated years of her life to secretly teaching slaves and free people of color to read and write, an activity that was illegal in Virginia.

In the letter she briefly talks about the death of two students in her class of 53 in the day. Sadly just a month later, Peake would die the next month of tuberculosis at the age of just 39.