Andrea Morales

The Education of Bill Oliver

How a letter to Barack Obama tells the story of two strangers who became family, and one lifelong Republican’s journey to a new kind of patriotism

Word came that President Barack Obama wanted to see some of the mail just the day after he took office. Mike Kelleher was the director of the Office of Presidential Correspondence (OPC). He got the call from the Oval saying the president wanted to see five letters. Then they called back with a correction. The president wanted to see 15 letters. They called back one more time. He wanted to see 10 that day, and every day.

“It was a small gesture, I thought, at least to resist the bubble,” Obama later told me. “It was a way for me to, every day, remember that what I was doing was not about me. It wasn’t about the Washington calculus. It wasn’t about the political scoreboard. It was about the people who were out there living their lives, who were either looking for some help or angry about how I was screwing something up.”

And why should the president be the only one reading 10 letters a day? What about everyone else in the West Wing? Surely Obama’s advisers and senior staff could benefit from seeing this material.

By the time Bill Oliver wrote to the president, in June of 2012, advancing the mail’s reach had become an overarching OPC mission. Employees there began to see it as their obligation to the letter writers, and their obligation to policy makers, and, if you got them talking about it long enough, their obligation to America: Be a megaphone for these voices. Open all the channels, full blast.

Fiona Reeves, an OPC staffer who soon became the office’s director, developed a distribution list, and kept adding to it. Letters to the president, dozens of them, just popping into people’s inboxes. Why not? And not just the 10LADs—the president’s 10 letters a day—but also others from the sample piles. “We send out batches of letters we think are striking,” she said. At first she worried about being an annoyance, but then she got bold. “I hope people read them; that’s why I spam them. But, I mean, they don’t have to read them.”

They did. Soon people started asking why they weren’t on the distribution list. The people in OPC came to know which people in the West Wing were particularly tuned in to the letters. The OPC staff came to regard these people as special agents, ambassadors, and they had a name for them: Friends of the Mail.

Bill Oliver does not want anyone to know where he or his family live, not the town, not even the state. MS-13, the most violent street gang in the Western Hemisphere, has a presence even in his sleepy city, and if gang members want to find someone, they can.

Needless to say, this has been an education. He is not the person he once was. He just turned 80.

The reckoning for Bill Oliver began in 2011, when he was on a trip to El Salvador. He had long since retired from teaching, had raised two kids with Sandra, his wife of nearly a half century, and they had fled the Snow Belt for the Sun Belt. He signed up to teach a few courses at the local college to keep his mind active. Taking students on a study-abroad trip to Central America was about waking them up. Showing them how the other half lives. “Appreciate what you have.” They were international-business majors studying things like finance, predictive analytics, and best practices in marketing-management strategies. Bill was a lifelong Republican who believed in things like small government, low corporate tax rates, and tight border security.

The dinner the villagers put on was cooked in a big pot boiling over an open flame. Bill wanted his students to see that. The coconut milk came out of the coconuts that they had seen boys pull off the trees. Real coconuts. Before they ate, the local kids challenged Bill’s students to a soccer game. Those kids had bare feet. Bill took his students aside. He said, “Now, don’t be rude. Make sure you let them win.” The local boys completely demolished the American college students. “Well, there you go,” Bill said. “Would you look at that? Look at that. Look at these people; they have no shoes, they have nothing, and they appear happy!”

After dinner, Bill got to know a man who said he was the father of several of the boys. His wife had cooked. Bill and the father stood in the kitchen, and the floor was dirt. The roof was corrugated metal, and the father didn’t have a shirt on. He was talking about his six sons, telling Bill all their names, and he said one of them was not there. That one had just turned 17 and his name was Quique. Key-kay. The father told Bill about MS-13, about the violence that was rapidly turning El Salvador into the murder capital of the world. He said Quique’s school was across the river, a good distance from the village, and that’s where the gang was. Gang members had been recruiting Quique, a lonely kid who needed friends and who made the mistake of listening to them. Soon he had found himself caught in a tragic dilemma. Gang members threatened to kill him if he didn’t join, and the price of admission was that he murder someone in his own family.

Quique’s only hope for survival was to flee. So the father put him on a bus with enough money, he hoped, to pay a coyote to smuggle him across the U.S. border. The father never heard from him again.

Bill is a kind and polite person, and any kind and polite person standing on a dirt floor in El Salvador under a corrugated-metal roof with a grieving father would have said the same thing. “Well, if there is anything I can do … ”

There was nothing Bill could do.

Two weeks after he got home, Bill told Sandra, “Well, I made a promise to the father that I would look for his son.” He can’t say for sure when or how the notion of a promise kicked in. He hadn’t promised anything. His students were finishing the semester, and they would soon move on to M.B.A.s and careers in big banks. Bill was not a busy man, not the way he used to be. If he took a shot at looking for the boy, perhaps he could be the man of honor he believed himself to be.

There was no way he’d be able to find the boy.

Bill Oliver was a lifelong Republican who believed in things like small government, low corporate tax rates, and tight border security. (Andrea Morales)

Bill started in Texas. He started in Houston. “I’m looking for a boy,” he said. Needle in a haystack. He could have stopped there, and his soul would have been at peace because, after all, he did try. He can’t say for sure when the compulsion to keep going kicked in, but if he’s honest, he’ll say at first it was about winning. Like you’re doing a crossword puzzle, and this one is not going to beat you. “I’m looking for a boy,” he said. “I’m looking for a boy.”

By 2012 more than 150,000 kids had been caught crossing the U.S. border, having run from countries in Central America, principally El Salvador, Honduras, and Guatemala, to escape MS-13. They get picked up, detained, and designated as “unaccompanied minors.” The Office of Refugee Resettlement, part of the U.S. Department of Health and Human Services, screens the kids for gang ties and holds them in shelters while attempting to place them with relatives or sponsors as they await hearings in immigration court.

New York is where Bill found Quique. The Office of Refugee Resettlement had sent him to a relative of some sort; this part is sketchy. Bill wrote a letter to the district court that Quique had been transferred to. He got no response, so he kept writing. He wrote so many times that the judge finally called him. You have to get an attorney and file motions if you want to do anything for the boy, she told him. Bill went online and learned about motions, and he wondered what, exactly, he wanted to do for the boy.

He thought about the father and the metal roof and the dirt floor. The conversation with the father, which had been redrawn in Bill’s mind as a promise, had bloomed into a full-blown test of character. He looked around his house, at the  pots, furs, masks, and other beautiful items crafted by villagers he had met on his various travels to remote parts of the globe. People who came by could see he was a worldly man who knew the taste of food cooked in pots over open flames.

To file the motion in district court, you had to indicate certain things. “I have the means to take care of him,” he wrote on the form. I have means.

When the motion was granted, they put Quique on a plane, and Bill went to the airport to pick him up. He recognized Quique because he was brown. Bill is big and round with a white beard, a Santa Claus look, not by choice. Quique went to him, and they walked together to Bill’s car. Bill spoke no Spanish, and Quique spoke no English. Bill didn’t know if Quique was coming for a day or a month or a year, and neither did Quique. Bill took Quique to a Salvadoran restaurant to make him feel at home. They ate pupusas, and the waitress had enormous breasts spilling exquisitely out of her shirt, and that was the only common language, and so that’s what they talked about with their eyes and their embarrassed laughter.

When Quique arrived, Bill said he would have to go to church on Sunday and eat dinner with him and Sandra, and he would have to go to school and learn English. (Courtesy of Bill Oliver)

There’s an app you can get on your phone that translates. You speak English into it, and it comes out Spanish, and vice versa, so for weeks at the kitchen table, that’s what they did. Bill asked Quique about his journey. In the beginning it had been exhilarating, Quique told Bill. His first time out of El Salvador. On a bus alone to Guatemala. He’d felt like a man. He felt the freedom of someone escaping death. In Mexico, with the strangers, in the back of trucks, he didn’t make friends. The Rio Grande was so shallow you could walk the first part. When it got deep, he took off his clothes and held them over his head and swam, and here’s where having grown up next to the ocean helped. Some of the others couldn’t swim. He put out his arm to help one of them, and that’s when he gave up trying to keep his clothes dry. It looked like the coast was clear, but none of them had ever been there before, and so they didn’t know where to look. The coast wasn’t clear. The person who grabbed him was not rough. He put Quique in a truck. The detention center was clean. You could earn points if you followed the rules. Points bought you candy, toothpaste, and time in the video-game room. He had never seen a video game. He spent all his remaining points on candy on the last day and then gave it to the other kids because you weren’t allowed to take it with you.

Bill told Quique about the promise he had made to Quique’s father.

Mi papá está muerto,” Quique said. My father is dead.

The news had come from the relative in New York. “Tu padre está muerto.” They said it was a heart attack.

“I’m sorry,” Bill said.

Listen to Quique talk about his journey:

Bill gave Quique his choice of bedrooms, and Quique picked the one in the corner. Bill said he would have to go to church on Sunday and eat dinner with him and Sandra, and he would have to go to school and learn English. Quique said he didn’t want to go to school. At the school, Bill told them; he said, “I’m going to be honest with you. He doesn’t want to be here, and he’s illegal.” They said they would figure something out. Bill hired a tutor. Quique discovered the Food Network, and that’s what he did after homework. He helped Sandra in the kitchen.

Bill and Sandra decided to adopt Quique. The lawyer said they were too old, and so was Quique. Bill could remain his sponsor until his hearing in immigration court when they decided what to do with him.

Quique got a girlfriend, Rebecca, a sunny, college-bound woman with sleek brown hair who said Quique was so much more mature than American guys. Quique made a lot of friends. He and Rebecca were in the back seat when the other car sped through the intersection. They were wearing their seatbelts. Rebecca was fine. Everybody was fine except Quique, whose bowel was severed by the seatbelt. At the hospital, Bill told the ER surgeon; he said, “I’m going to be honest with you: He’s illegal.” The surgeon said he would figure something out. When the people at church heard about the accident, they said they would figure something out. Rebecca’s parents said they would figure something out. It was a community coming together. The question of citizenship, papers, race, who belongs or who doesn’t—who is deserving and who isn’t—never came into it. It was people helping people, paying for the surgery, nursing Quique back to health.

Bill had no idea where immigration court was or how it worked. He bought Quique a pair of dress pants and a blue shirt. At the hearing, Bill made the point that Quique had cost the American taxpayer nothing. People were helping him out. Quique was doing everything right. He had followed the rules. He was in school, and he was learning English. Bill had letters praising Quique’s conduct from teachers and from church and even from the mayor, because Bill did know how to pull some strings.

The judge said there was no immunity for a kid who made an illegal crossing on account of MS-13. She said Quique had to go back to El Salvador.

“I’m sorry,” Bill’s attorney said. Bill told her he was going to appeal. If Quique were to go back to El Salvador, he would have to face the gang he had fled that wanted to kill him and that would almost certainly kill him now.

Bill’s attorney hung her head and looked at her shoes. Everyone, she said, appeals. Everyone had the same story. That same week, on June 15, 2012, President Obama was in the Rose Garden announcing a policy called Deferred Action for Childhood Arrivals (DACA). It allowed certain immigrants to escape deportation and obtain work permits.

Bill was desperate. He was not an Obama supporter. He was the opposite. But he felt like a changed man. Would that make a difference to the president?

Bill reflected on what, exactly, about him had changed. The entire saga could be summed up in one sentence: Bill had gotten to know a person who was in America illegally, and he had grown to love him.

Bill needed his letter to Obama to sound important. Just saying “Help!” seemed undignified.

Listen to Bill read his letter to Obama:

He told the president Quique’s story, and at the end he wrote:

Now what? What can we do? …

How can I help the young man of which I speak, and others like him?

He signed it, “William C. Oliver, Ph.D.”

At the White House, the OPC machine was in motion, just as it was always in motion.

Shailagh Murray, a senior adviser, was a Friend of the Mail. She told me that the constant flow of letters into the West Wing was part of the regular morning conversation among senior staff. “We’d receive them by email, and then different people would distribute specific letters that caught their eye. The chief of staff, Denis McDonough, would often distribute letters at our senior-staff meetings. Just flagging things that were interesting to him or that he found especially poignant. Everybody had a different definition of what they thought was a great letter. For me, a great letter was one that would make me feel confused about issues and expand my understanding of the implications of what we were doing.”

Dear Mr. President,

I have never had more conflicting emotions about a public figure. I was deeply discouraged when I heard about the ICE raids. But, you … have also fought hard to change the criminal justice system. There are many people in my social network that were unjustly criminalized because of their drug addictions. However, the consequences that drug convictions have on immigrants … remain inhumane under your administration …

I have been very disappointed in you. I have also never been more proud of a president before you …

Lisa K. Okamoto
South Pasadena, CA

Valerie Jarrett, Obama’s longest-serving senior adviser, became a Friend of the Mail. For her, the letters were a kind of nourishment. “When you’re having a really bad day in Washington, there’s nothing like picking up a letter from a citizen,” she told me. Sometimes she would be so moved by a letter she would pick up the phone and call the person. “I want to just emphasize: Washington is so impersonal,” she said. “Imagine your worst impression of what it would be like and then magnify that. It’s removed. It’s physically removed. You get caught up in the sausage making.” She believed that the administration’s emphasis on continued contact with constituents was a reflection of Obama’s own struggles with that separation. “He did not enjoy the isolation. He spoke about it often. That human interaction—he craved it.”

Calling a letter writer seemed to her like a perfectly natural thing to do, like checking in with a neighbor. “I’d ask people what motivated them to write, and more times than not they would say they wrote out of a feeling of frustration or desperation or inspiration, love.”

Love, frustration, desperation—that was the stuff you couldn’t get if you were caught up in the sausage making. The letters were access. The letters were emotion, context, and narrative. I reached out to other Friends of the Mail and found ideas like that emerging and reemerging, going back to the earliest days of the administration and the days of the campaign. David Axelrod, who served for years as Obama’s senior adviser and chief strategist on both of his presidential campaigns, said the letters were Obama’s lifeline from the start. “They were more than a kind of ceremonial nod to, you know, to the grass roots,” he said. “Remember, you have a guy here who four years before—a little more than four years before—was a state senator. Basically representing some communities on the South Side of Chicago. And his habit was to travel that district and interact with people. And so to go from that experience in four years to being the president of the United States is, you know—it only accentuates the loss of contact.”

One thing I noticed about all of the Friends of the Mail I reached out to was they were delighted to learn that people in OPC thought of them as Friends of the Mail—“Oh, it’s so true!”—and they readily volunteered names of others I should know about. There were recognizable names like Senator Dick Durbin of Illinois, White House Press Secretary Robert Gibbs, and the speechwriter Jon Favreau, as well as plenty of people I’d never heard of, and the names kept multiplying—two more here, six more there, and then each of those people had more names. It got so I started wondering, Is anybody over there in the West Wing not a Friend of the Mail?

Probably not, Chris Lu told me. He served as deputy secretary of labor for the administration and White House Cabinet secretary; before that he was in the trenches on the transition team and in Obama’s Senate office. Chris talked about getting “steeped in the ethos of how we do mail in Obama world” as a kind of credentialing. “It’s one of the things that was really kind of ingrained in us,” he said. If you didn’t appreciate the mail, you wouldn’t have lasted. In Obama world, letters were part of the deal. “The president would say, ‘Send this to Secretary [Tom] Vilsack, and I want to know what his response is,’” he told me. “And believe me, those letters went. I would send it to, in this case, to the Department of Agriculture. And they understood. A fire was lit under those agencies to respond.

“I think it’s all part of the broader spirit of transparency,” he said. “The idea is that government works best when people can participate in that government. And look, obviously when you’re in a country of 300 million, it’s hard to do that. But people express their views not only by voting; people express their views by writing letters.”

The speechwriter Cody Keenan (Friend of the Mail) said the letters were constant fodder for speeches. “The president will just call me upstairs and say, you know, ‘Read this letter; this is awesome; let’s work this into something,’” he told me.

“If there was a way to make every letter he got for eight years a piece of data somehow,” Cody said, “put all that data together, that would tell a pretty great story.”

“I’ve always looked at the letters as hopeful,” Cody added finally. “It’s even—no matter how painful or upset your letter might be, there’s still something hopeful about sitting down and thinking that maybe somebody will see this. There’s a hope that the system will work. Even if you’re sitting down to write, ‘Dear Shit for Brains,’ there’s a chance that someone might read it, you know?”

Listen to Bill talk about getting to know Quique:

For Shailagh the letters became a resource for study, a sociology project, a history lesson. “I started looking back through letters chronologically, to get a different version of the presidency,” she told me. “Establishing the public trajectory of the presidency as opposed to the legislative one or the policy calendar. This was the outside looking in.”

One of the things she found was confirmation that these voices provided a kind of emotional nudge to decision makers.

Senior staff could have, after all, opted to synthesize the voices coming out of the mail room. They could have made charts indicating trends. “Imagine if Obama received them and we digested them for him,” Shailagh said. “Just summaries of the letters, for instance. Any of these letters you could condense into a couple sentences, get the point across, without the texture and the voice and the color. And he would certainly be able to track what people were concerned about, you know?” But you wouldn’t have “the depth; the personal, plaintive cries; and the stories as vignettes. All those things would be lost.”

The human side of the story, the ideas you can’t squeeze into a briefing memo or translate into bar graphs or dots on a chart. The voices of letter writers were a constant chorus in the background, pop songs you couldn’t get out of your head, the tunes that defined a culture.

Like probably every other person who wrote a letter to the president, Bill had no idea that interns and staffers with pencils were busily making their marks.

Sample/Immigration Hardship

Bill had no idea that Obama, too, was making his marks.

Reply,” Obama wrote, on the top, in blue ink. And then along the right side he scribbled: “Can we find out from Cecilia what the best options for this young man would be—does he qualify for deferred action?”

Quique with Bill and Sandra at their home (Andrea Morales)

Bill was surprised when he got a personal note back from the president on a white card, handwritten. It’s here somewhere. If he finds it, he’ll show you. Frankly, the personal note didn’t mean nearly as much to him as the phone call he got from a White House staffer who instructed him to call a certain number at a certain time; the person he reached was with U.S. Citizenship and Immigration Services, and she asked Bill questions about Quique’s situation.

Among other requirements, to qualify for deferred action you had to be younger than 31 on June 15, 2012, and you had to have come to the United States when you were younger than 16, and you had to have lived in the United States since June 15, 2007. The Pew Research Center estimated that as of 2014, up to 1.1 million people were eligible.

Quique wasn’t one of them. He was too old, and he hadn’t been in the United States nearly long enough. DACA was of no help to Quique.

“I’m sorry to hear that,” Bill said.

Bill told Quique to make sure his shirt and dress pants were clean and ironed for whenever the appeal hearing came up, and he called his attorney for an update.

She said something happened. She said Quique’s case had been abruptly closed. “Prosecution discretion,” she said.

Bill would prefer not to disclose the details of Quique’s immigration status, especially given the current climate, but the news is good: “He has the lowest status you can get for someone to stay in this country legally, but he’s here legally.”

Bill would never know if the ruling had anything to do with his letter to the president; he wondered whom he would even ask. Did it matter? Quique would not have to go back to El Salvador. Quique had a new life. America had given him a second chance. It turned out that finding Quique was about more than finding Quique. For Bill, it was a journey to a whole new kind of patriotism.

Bill took Quique shopping for an engagement ring. Quique and Rebecca got married, and on their honeymoon they watched dolphins swim, and they got back in time to go to church, where Bill was leading the singing.

This article has been adapted from Jeanne Marie Laskas’s forthcoming book, To Obama: With Love, Joy, Anger, and Hope. Audio by Erin Anderson; additional research by Rachel Wilkinson.