The letters that make Obama long for his community-organizing days
By Eli Saslow,
It had become one of President Obama’s signature routines in the White House, a habit he mentioned in dozens of meetings and hundreds of speeches: Every night just before bed, he read 10 letters pulled from the 20,000 that Americans sent to him each day. The notes reminded him of why he wanted to be president, he liked to say. He called them his most intimate link to the people he governed.
But by the time I visited the president in the Oval Office earlier this year to talk about the letters, some of his aides had begun to wonder if Obama’s affection for the mail had outworn its usefulness. Gone were the post-inaugural thank you notes. Instead, Obama sometimes received letters addressed to “Dear Jackass,” “Dear Moron” or “Dear Socialist.” People wrote because they had lost their jobs, their homes or their relatives in the wars. Each day’s mail brought another deluge of hard luck and personal struggle, a wave of desperation capable of overwhelming the senses.
Most sobering of all for Obama, his self-described “direct connection” to Americans had also awoken him to a growing disconnect. People wrote because their problems demanded immediate attention, and yet the process of governing the nation was so slow that Obama sometimes felt powerless to help them.
A few times during his presidency, Obama admitted, he had written a personal check or made a phone call on the writer’s behalf, believing that it was his only way to ensure a fast result. “It’s not something I should advertise, but it has happened,” he told me. Many other times, he had forwarded letters to government agencies or Cabinet secretaries after attaching a standard, handwritten note that read: “Can you please take care of this?”
“Some of these letters you read and you say, ‘Gosh, I really want to help this person, and I may not have the tools to help them right now,’ ” the president said. “And then you start thinking about the fact that for every one person that wrote describing their story, there might be another hundred thousand going through the same thing. So there are times when I’m reading the letters and I feel pained that I can’t do more, faster, to make a difference in their lives.”
For the past year, I had been reading Obama’s mail and traveling across the country to spend time with some of the letter-writers. I had learned firsthand that people tended to write to the president when their circumstances turned dire, sealing a prayer into an envelope as a matter of last resort.
I had also read many of the president’s handwritten responses, in which he sometimes assured in black ink that “things will get better,” even if he wasn’t so sure himself. I had watched him correspond with a Michigan woman while she went through bankruptcy; with a fourth-grader while she attended one of the country’s worst schools; with a mother while she waited to hear from her son in Afghanistan; with a cleaning woman while she battled leukemia and worried about paying her medical bills.
Months after these people wrote to the president, when I mentioned their letters to Obama, he remembered the details of their lives. Their letters had shaped his speeches and informed his policies, but it was their personal stories that stuck with him. “Reading these letters can be heartbreaking,” he said. “Just heartbreaking.”
He said his nightly reading in the White House sometimes made him pine for his days as a community organizer back in the 1980s, when he was making $10,000 a year and working on the South Side of Chicago. He had just graduated from college, and he bought a used car for $2,000 and spent his days driving around to the city’s housing projects to speak with residents about their lives. He became familiar with many of the same issues that would flood his mail 25 years later: housing calamities, chronic unemployment and struggling schools.
Obama’s fellow organizers in Chicago considered him a master of hands-on, granular problem-solving. He was skinny and boyish, a good listener, if still a bit naive; and some of the older women in the housing projects made a habit of inviting him into their homes and cooking for him. He looked around their apartments, keeping a log of maintenance issues, and then delivered that list to the landlords. He helped arrange meetings with city housing officials to talk about asbestos problems. He established a tenants rights organization, founded a job-training program and led a tutoring group that prepared students for college.
When he left for Harvard Law School after three years in Chicago, Obama knew he wanted to become a politician, a job that would allow him to listen to people’s problems and enjoy the simple satisfaction of solving them.
Now he was the most powerful politician of all — but fixing problems seemed more difficult and satisfaction more elusive. He had yet to make progress on key campaign promises to reform education and immigration. Just this past week, his jobs bill failed to move forward in the Senate. When we spoke, Obama didn’t blame the gridlock and partisanship of a divided capital, but instead stressed the paradoxical limitations of his office.
Meanwhile, the letters kept coming. The president said he wondered whether a community organizer might have an easier time responding to them.
“The people were right there in front of me, and I could say, ‘Let’s go to the alderman’s office,’ or, ‘Let me be an advocate in some fashion,’ ” he told me. “And here, just because of the nature of the office and the scope of the issues, you are removed in ways that are frustrating.
“Sometimes, what you want to do is just pick up the phone and say, ‘Tell me more about what’s going on, and let me see if I can be your social worker, be your advocate, be your mortgage adviser, be your employment counselor.’ So what I have to constantly reconcile in my mind is that I have a very specific role to play in this office, and I’ve got to make a bunch of big decisions that you hope in the aggregate will end up having a positive effect over this many lives. But you can’t always be certain.”
An aide walked into the Oval Office and pointed at her watch. Our time was up. The day was almost over. Another packet of 10 letters was on its way to Obama’s residence, tucked inside a purple folder in his nightly briefing book.
Later that night, he would sit down on his couch, open the folder and find missives from rural Arkansas and downtown Detroit, notes of inspiration and devastation. He would read all 10 letters and reply to one or two. Sending a response still allowed him to provide one thing immediate and concrete.
“It lets them know I am listening,” he said.
And sometimes listening was all he could do.
Eli Saslow, a Washington Post staff writer, is the author of “Ten Letters: The Stories Americans Tell Their President.” This article is adapted from that book with permission from Doubleday.