The letters that make Obama long for his community-organizing days

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.

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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.”