What Barack Obama should have written in his letter to Donald Trump

Photo: AP/Pablo Martinez Monsivais

I really wanted to like the letter that Barack Obama left in the Oval Office for Donald Trump. Ultimately, though, it’s nothing but platitudes. It certainly hasn’t helped.

Imagine for a moment the situation of outgoing President Obama writing a letter for incoming President Trump on Inauguration Day in January. On substance and policy, the two have little in common. On style, they could not be more different. One’s life has been wholly dedicated to government, the other has no government experience.

So Obama wrote a cordial and, ultimately, meaningless greeting. If you love Obama you may think this is classy; if you detest him and like Trump, the letter seems condescending.

The most honest and substantive part of it is this: “I don’t know that any advice from me will be particularly helpful.”

Read it for yourself. Here’s the whole text, as revealed by CNN:

Dear Mr. President –

Congratulations on a remarkable run. Millions have placed their hopes in you, and all of us, regardless of party, should hope for expanded prosperity and security during your tenure.

This is a unique office, without a clear blueprint for success, so I don’t know that any advice from me will be particularly helpful. Still, let me offer a few reflections from the past 8 years.

First, we’ve both been blessed, in different ways, with great good fortune. Not everyone is so lucky. It’s up to us to do everything we can (to) build more ladders of success for every child and family that’s willing to work hard.

Second, American leadership in this world really is indispensable. It’s up to us, through action and example, to sustain the international order that’s expanded steadily since the end of the Cold War, and upon which our own wealth and safety depend.

Third, we are just temporary occupants of this office. That makes us guardians of those democratic institutions and traditions — like rule of law, separation of powers, equal protection and civil liberties — that our forebears fought and bled for. Regardless of the push and pull of daily politics, it’s up to us to leave those instruments of our democracy at least as strong as we found them.

And finally, take time, in the rush of events and responsibilities, for friends and family. They’ll get you through the inevitable rough patches.

Michelle and I wish you and Melania the very best as you embark on this great adventure, and know that we stand ready to help in any ways which we can.

Good luck and Godspeed,


Translation: Good Luck

This is friendly, direct, and ultimately platitudinous. Stripped of weasel words (“remarkable,” “Millions,” “expanded,” “clear,” and so on), it’s just stuff everyone already knows. Here’s a shorter translation:

Dear Mr. President –

You won. We’re counting on you. After 8 years of being president I have no real advice for you. You were lucky. So was I.

Don’t forget America’s children. Please don’t destroy our position in the world. Respect the government and how it works.

Hug your wife and kid.

Good luck.


With hindsight, here’s what Obama should have written

No one, Obama included, could have predicted the contentious and dizzying array of things that happened since Trump took office. Clearly, Obama’s advice was inadequate. With the benefit of hindsight, and making the dubious assumption that Trump would actually listen, here’s what Obama should have written:

Dear Mr. President –

You are about to become the most powerful person in the world. But there are limits to your power, because ours is not the only country in the world and the presidency is not the only center of power in America. If you ignore these realities, you will never get anything done. If you want to succeed, here are some tips:

  • Get a chief of staff who you trust and empower them to manage access to your time. Otherwise you will drown in random advice and fail to focus on important priorities.
  • If you don’t like to read briefing papers, surround yourself with smart people who can, and who you trust. Listen to them and trust their advice.
  • Remember that world leaders are independent and dedicated to the well-being of their own nations and people, but share an interest in world peace and prosperity. Don’t insult them; you’ll need their help.
  • Remember that Congress is made of of 535 individuals with their own agendas. Make friends with the leaders in Congress and get a world-class legislative affairs aide who can work with them. Take positions they can support and then rally your own supporters behind those positions. Do your homework on legislation; details matter to these people! If you don’t, they’ll demonstrate their power over legislation and humiliate you.
  • Don’t piss off the press. They bite. And they buy ink by the barrel.
  • Respect the investigative powers of the Justice Department and FBI. If you’ve done anything wrong, don’t try to squash them. It will come back to bite you. When it comes to investigations, they’ll eventually get their way.
  • Reach out beyond your base, or you’ll never get elected, and the Republicans will lose ground while you’re in office.
  • As John Adams said, “Facts are stubborn things.” Keep them straight. You don’t want to get a reputation for lying to America.
  • And finally, kill Kim Jong-un as soon as possible. I have this intuition that he’s going to cause trouble.

By the way, you should probably keep the golf outings to a minimum. Every time I went golfing people made fun of me for wasting time instead of governing. It’s a bad look.

Call anytime. I won’t be nearly as busy as you are.


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  1. I think that’s a lot more words than would have been necessary. “Dear Don, Don’t be a douche,” would have sufficed. A lot less time and ink required to write it. Same result.

  2. The letter was transparently written for future historians, who will use it to contrast Obama (“classy till the end”) with Trump (“crass from the beginning”). Obama was playing the long game here.