Humour to humility: Letters presidents leave behind in the Oval Office

Every four or eight years, as America’s leadership changes hands, an almost invisible ritual takes place behind the closed doors of the Oval Office.

It’s a rare instance of unfiltered communication between peers, meant to be candid, brief, and private. Some presidents take the opportunity to share wisdom, others opt for humour, but each note becomes a small, enduring part of the American tradition.

The outgoing president leaves a personal letter on the Resolute Desk—an heirloom of American history used by almost every president since 1880—for the incoming head of state.

The tradition began in 1989, when Ronald Reagan left a note for his successor, George H.W. Bush. Reagan simply wrote a short, warm message.

Since then, every president has left a parting letter, handwritten and varied as the individuals themselves, blending advice, reflections on the burdens of the office, and sometimes, an unexpected sense of camaraderie.

Joe Biden, too, is expected to leave a letter for Donald Trump upon his departure on January 20, 2025.

A ‘generous’ letter by Trump

Trump chose not to follow many social traditions while handing over the presidential baton to Biden at the end of his first term in 2021.

Despite skipping Biden’s inauguration, Trump did leave Biden a letter. In a rare public comment on the note, Biden described it as “shockingly gracious” and “generous,” though he withheld specifics, calling it “private” and hinting that he might share its contents only after speaking with Trump.

In contrast, letters written by Presidents Reagan (1989), George HW Bush (1993), Bill Clinton (2001), George W. Bush (2009) and Barack Obama (2017) are now public.

The contents of Trump’s note remain unknown, unlike many other letters in this tradition, which have gradually entered the public domain.

Trump on Obama’s letter

In his letter to Trump, Obama underscored the transient nature of the Oval Office: “That makes us guardians of those democratic institutions and traditions… it’s up to us to leave those instruments of our democracy at least as strong as we found them.”

Trump praised the letter as “beautiful” and “very well-thought-out,” later thanking Obama for taking the time to write such a “long” message.

Others honour the quiet tradition

Not all presidential transitions have been as divisive as the Trump-Biden handover.

“You have just begun a fantastic chapter in your life. Very few have had the honour of knowing the responsibility you now feel. Very few know the excitement of the moment and challenges you will face,” George W. Bush welcomed Obama with those lines into the Oval Office.

Many Obama officials would later credit the Bush team for executing a notably smooth transition, which stood out given the two men’s divergent politics.

In 2001, Bill Clinton wrote George W. Bush a letter reflecting his own optimism and admiration for the role: “You lead a proud, decent, good people. And from this day, you are the President of all of us. I salute you and wish you success and much happiness.”

Referring to a “time of profound and largely positive change”, Clinton told his White House successor that the burden of the US presidency -- albeit great -- is often exaggerated. “The sheer joy of doing what you believe is right is inexpressible.”

Despite the bitterness of losing his re-election bid, George H.W. Bush wrote to Clinton in 1993. He chose to be magnanimous, writing: “Your success is now our country’s success. I am rooting hard for you,” a comment praised by historians as a rare artefact of political humility.

Then there is Reagan’s original note. His letter to Bush, on Oval Office stationery – an elephant beset by Turkeys. Elephant is the symbol of the Republican party to which both Bush and Bush belonged. The illustration was adorned with the words “Don’t let the turkeys get you down.”

In a flash of his trademark humour, Reagan advised Bush to “stay away from overly confident colleagues who could keep him from achieving his best.” Reagan even scrawled a final nod to their long partnership: “I’ll miss our Thursday lunches.”