Take a Closer Look at Letters by Barack Obama Saved by His College Roommate

What was it like to know Barack Obama in this early twenties? ROADSHOW learned the answer when Obama’s former college roommate, Phil, brought in letters and postcards written to him by the future president, detailing his life and early career in Chicago.

Mar 16, 2020

BY Melanie Albanesi

During ROADSHOW’s 2019 event at the Crocker Art Museum in Sacramento, California, a guest named Phil brought in letters, postcards, and cards written to him by the future 44th president of the United States, Barack Obama. Phil explained to Books & Manuscripts appraiser Tom Lecky, that he and Obama were roommates at Occidental College in Los Angeles their freshman and sophomore year, later transferring to Columbia College in New York City where they remained roommates for the first semester. After graduation, the pair stayed in touch, writing back and forth to one another.

The letters and postcards Obama wrote to Phil ranged in date from March 1983 through September 1999, consisting of Obama’s career updates, news on new girlfriends, notes on Phil’s writing — the pair appeared to have traded original short stories from time to time — as well as Obama’s musings about his life in Chicago and New York. The final note in the archive, dated September 1999, shared a personal yet significant moment in the future president’s life:

9/99
Phil —
Great to hear from you!
Main news:
1) Michelle and I have a beautiful baby daughter, Malia, one year old.
2) I’m running for Congress.
Life is hectic but good!
Barack

Life According to Post-Grad Obama

Phil emphasized how, early on, he knew his roommate would go on to have a successful future, yet he couldn’t predict exactly how:

“Well, he was a very charismatic, fun guy. You could tell he'd be successful at something, very thoughtful. I didn't see him as the first black president of the United States, but I knew he'd be successful at something.”

The letters themselves offer little tidbits of Obama’s personal history, wrapped around ordinary details one would share with a friend. In the earliest letter in the archive, dated March 3, 1983, Obama reflects upon the hum-drum ordinariness of his life at Columbia University in New York, and writes about his plans to shift to the working world:

Been sending out some letters of inquiry to some social service organizations and will be making up a resume (no comment) soon! I’ve also written an article for the Sundial purely for calculated reasons of beefing up the thing. No keeping your hands clean, eh?

When he wrote his next letter, dated November 20, 1985, it was two years later and Obama had been working in the South Side of Chicago as a community organizer. In the three-page letter, he shares his insights on the racial divisions in Chicago as well as the issues surrounding the impact of the gentrification of the neighborhoods he worked in:

I work in five different neighborhoods of differing economic conditions. In one neighborhood, I’ll be meeting with a group of irate homeowners, working-class folks, bus drivers and nurses and clerical administrators, whose section of town has been ignored by the Dept. of Streets and Sanitations since the whites moved out twenty years ago. In another, I’ll be trying to bring together a group of welfare mothers, mothers at 15, grandmothers at 30, great-grandmother at 45, trying to help them win better job-training and day care facilities from the State. In either situation, I walk into a room and make promises I hope they can help me keep. They generally trust me, despite the fact that they’ve seen earnest young men pass through here before, expecting to change the world and eventually succumbing to the lure of a corporate office. And in a short time I’ve learned to care for them very much and want to do everything I can for them. It’s tough though. Lots of driving, lots of hours on the phone trying to break through lethargy, lots of dull meetings. Lots of frustration when you see a 43% drop out rate in the public schools and don’t know where to begin denting that figure. But about 5% of the time, you see something happen — a shy housewife standing up to a bumbling official, or the sudden sound of hope in the voice of a grizzled old man — that gives a hint of the possibilities, of the people taking hold of their lives, working together to bring about a small justice. And it’s that possibility that keeps you going through all the trenchwork.

A Man of Hope

Back in Sacramento, Lecky told Phil that it is in this letter where we see incredibly important content. He points out that Obama uses the word “hope” in this letter, the word which would become an iconic element of his presidential campaign two decades later.

As the letters go on, they continue to track Obama’s path forward to his decision to run for Congress in 1999. In a letter dated October 21, 1986, he tells Phil how he was promoted to Project Director for “a spin-off of the original organization,” where he says that the “scope of the problems here are here — 25% unemployment; 40% high school drop out rate; infant mortality on par with Haiti — daunting, and I often feel impotent to initiate anything with major impact. Nevertheless, I plan to plug away at it at least until the end of 1987. After that, I’ll have to make a judgment as to whether I’ve got the patience and determination necessary for this line of work.”

Following communication from Phil announcing his engagement, Obama tells his friend how he is “now considering going to law school,” which eventually comes to fruition in 1988, when, in a letter apologizing to Phil for missing his wedding, Obama tells him, “I’ve decided to back to Law school this Fall [sic] — probably Harvard.”

In one of the final, more personal letters to Phil, dated April 1994, Obama shares news of a family of his own, and introduces Phil to his formidable new bride, Michelle:

I must say that I’m thinking about a family of my own. In fact, I’m more than half-way there, since I got married last year, to Michelle (picture enclosed). Other news — I’m a practicing lawyer in Chicago, mostly civil rights cases; I teach a course at the University of Chicago law school; and I’m finishing up a book that will hopefully be published next year. I hear from Imad from time to time; he seems to be doing fine in Pakistan. Haven’t heard from Carpenter since a visit from him and Beth while I was at Harvard. I still have the nicotine habit, but Michelle has made me promise to quit as soon as the book is done. Otherwise, no babies! Hope all three of you have a fine summer and look forward to hearing from you soon.
Love —
Barack

Back in Sacramento, Tom Lecky, impressed with the personal detail and nuances of the content, said that he could see why the roommates had remained close:

“You were someone that he trusted and shared a time of his life with while he was in his formative years…And I think it’s interesting that not only do we see the word ‘hope’ in this letter, but we see ‘love.’ These are two very simple, very basic four-letter words. And they show him in his formative years, as he’s developing what would evolve into his Presidential politics, maybe two pillars of — of his philosophy.”

With this in mind, Lecky gave Phil’s archive a retail value of $25,000 and an insurance value of $40,000.
You can read some more of the archive below.