When I reached New York Times columnist David Brooks in D.C., I was most interested in getting his impressions of the University of Chicago from which he graduated as a history major in 1983. We skipped talking about his new, bestselling book, The Road to Character, in which he decries today’s focus on “resume virtues” by exploring the lives of people—from St. Augustine to Dwight Eisenhower—who exemplified what he calls “eulogy virtues.”

I couldn’t let him hang up without asking him about his obvious admiration for Rahm Emanuel, several times the subject of his columns, as well as David Axelrod, whom he once described as his “hero,” and Barack Obama, who is said to call Brooks his favorite conservative.

Because Brooks’s twice-a-week op-ed columns (he has written hundreds of them over the past 14-plus years) often flirt with piousness, his recent split from his U. of C. classmate—Jane Hughes, who converted to Judaism and changed her name to Sarah Brooks—has been snarkily and gleefully noted by his critics. I’ve noticed that he is increasingly the butt of derision, and I asked him about that. “It’s the universal experience of all opinion columnists,” he said, claiming that he pays little attention, but he does quickly scan the moderated comments under his column to see if there’s anything to be learned from them. Female opinion writers, he added, “get it much worse.”

Brooks, 53, was born in Toronto, where his father was working on his PhD in English at the University of Toronto. He lived in New York City as a boy and then in suburban Philadelphia as his father followed college teaching jobs. Brooks went to Radnor High, an upper-middle-class suburban school, which he describes as “not quite as fancy as New Trier” but, nonetheless, a “John Hughes Breakfast Club kind of place.” He was not a good student—he graduated in the bottom half of his class.

Here’s an edited transcript of our conversation:

I’ve read or heard you say that you wanted to go to an Ivy League school. How did you end up at the University of Chicago?

Yeah. I knew I couldn’t get in. I applied to Brown, Wesleyan, and Columbia. Wesleyan was my first choice and then Brown. I was rejected everywhere but U. of C. [Brooks told Chicago Maroon writer Noah Weiland in 2013 that during his years at Chicago, 70 percent of applicants were admitted.]

Today you’re considered a kind of moderate-leaning conservative. What were your politics when you were a student here?

I worked on the John Anderson for President Committee at the U. of Chicago. [A 10-term Republican congressman from Illinois, Anderson ran for president in 1980 as an independent.] He had a burst of popularity. We went from one person to the largest student body organization for a week. Then he faded. He had a moment of popularity. He was a moderate, closer to where I am now. But I started to go to the library and read a lot of left-wing magazines, New Masses and others. I drifted left. By senior year I was a Democratic Socialist in the Michael Harrington tradition. 

In your senior year you were selected to make the socialist case in a televised debate with free-market guru Milton Friedman.

It was on PBS. Friedman had left for Stanford, so we flew out there. It’s on YouTube, and it's embarrassing how he crushed me. The debate was in five episodes and called “Tyranny of the Status Quo.” Friedman was amazingly respectful. He took us out to dinner every night in San Francisco and talked to us. I remember what I learned. He was a genuine teacher and wanted to introduce us to free-market, libertarian ideas.

I just happened to write about U. of C. graduate and 2016 presidential candidate Bernie Sanders. He called himself a socialist in college and in the U.S. Senate he calls himself a Democratic Socialist. What’s your take on him?

I’m so far to his right. I sort of respect him. It's amazing that he thinks he could get elected as an independent. [Sanders has said that, by necessity, he’ll run as a Democrat.] He has incredible drive and forcefulness, uncompromising. He’ll have a moment. Not a chance in hell he’ll win.

Could you imagine voting for Hillary Clinton in 2016?

I never talk about whom I’ll vote for, but, yes, I could imagine.

You stayed in Chicago after graduation, working as a bartender at the University’s Quad Club while trying unsuccessfully to sell article ideas to magazines. Then you worked for a weekly called the Chicago Journal and then as a police reporter for City News Bureau. Did you ever think about staying here?

Yeah, my career happened to take me to New York. But covering Chicago politics, I couldn’t imagine why national politics are more interesting to anyone. Danny Rostenkowski had the choice to be mayor of Chicago or chairman of the House Ways and Means Committee. He decided to stay in Congress. I totally couldn’t understand why he didn’t want to be mayor of Chicago. There are three places I could see myself living: New York, D.C., and Chicago.  

The phrase “Obama’s favorite conservative” is attached to your name. Does that bother you?

I don’t know if it’s true anymore. I think highly of the guy.

How often have you been at the Obama White House? I’ve read 25 to 30 times.

It’s a little higher; about 40 at this point.

And these are off-the-record meetings? Do they stay that way?

They pretty much stay off the record. Not that he says anything very substantive. These are policy-oriented meetings, like policy seminars.

Are there other conservatives in the room?

I might define the rightward edge.

You have described Obama as “writerly” and you have publicly praised his book The Audacity of Hope. Are you looking forward to the memoir that will surely appear after he leaves office? (In 2006, Brooks wrote a valentine to Obama titled “Run, Barack, Run,” urging him to run for president in 2008.)

It’s hard to write about the presidency. Decisions are not dramatic. He’ll write a phenomenal memoir. He has a writer’s eye, the penchant for being a distant observer. But when he’s stuck in the middle of the maelstrom, will he be able to get back to the writer mentality; step out and return to the writerly frame of mind? He could write a great memoir, as opposed to one merely justifying himself .

I’ve read that when Rahm Emanuel was Obama’s chief of staff he would call you shortly before your Monday and Thursday deadlines and ask if tomorrow would be a good day for him and his boss. Is that true? 

That may have happened once. Rahm is the kind of guy who does a lot of calls. When he does call, it’s short, interested in letting me know what the administration is doing. It’s a 90-second phone call, then goes off.

Has Rahm ever screamed at you about something you’ve written?

When he was about to leave Washington to go to Chicago and run for mayor, I wrote a column about him. [The column described Rahm as a man of “ample heart,” a “warmhearted Machiavellian,” a man who “speaks the language of loyalty and commitment, not the language of calculations and self-interest.”] Then we saw each other at a Bruce Springsteen concert in D.C. He didn’t scream, he just dismissed the column as crap. I’ve seen him express anger, but he's never given me the complete work over.

Are you in touch with him now that he’s mayor?

Yes. When I email him, he gets right back to me. He’s communicative. He stays in touch via email and calls. We’re both interested in education reform, so he’ll call me to give me a head’s up about what he’s doing, say, with community colleges.

Education reform? Are you, like Rahm, an advocate for charter schools?

Yes. I think charter schools should remain in mix. When charters were new, there were some good charters and some bad. But as time goes on, we’re learning which models work. Charter schools are beautiful labs for innovation.

What about another Chicago character, David Axelrod?

I think the world of Axelrod. I last saw him at a book party for his book in Washington. He’s an earnest believer in his causes. Some consultants are cynical; for some it’s just a game. He really believes in the Institute of Politics that he’s creating at the U. of C. If you thought he took it lightly, you’d be wrong. If he was just a consultant, he wouldn’t spend all this time building a student program, a first-rate academic enterprise with complete balance.

There’s also the personal side. He grew up, as I did, in New York’s Stuyvesant Town. I went to U. of C. as did he. When I was working at the City News Bureau as a police reporter, he was chief correspondent covering City Hall for the Tribune. He was years beyond me, but doing what I wanted to do.”

What do you think of the Obama library and museum coming to Chicago? One U. of C. professor has spoken out against the University having any ties to the museum part of the complex because presidential museums are, after all, propaganda machines for a president’s legacy.

I am on the board of trustees at Chicago. I didn’t have inside information, but I was delighted. I think if the president is going to help African-American young men, which he has pledged to do now and after he leaves the White House, what better place than the South Side of Chicago. Total win for the city. He doesn’t need to go to New York.

But it appears that his foundation, or a part of it, will go to New York and that that’s where the Obamas will live. It’ll be analogous to Bill Clinton—his library and museum in Little Rock and his foundation and life in New York.

I didn’t want him totally going to New York. And I don’t agree that presidential libraries/museums are merely propaganda arms. Sometimes they can be; some museums are shrines. But some have turned into places where there are conferences and panels and the issues of the day are debated. Even the [George W.] Bush Library at SMU [Southern Methodist University] has quite a good program.

I think that the fact is that for universities, and especially for the University of Chicago, more avenues to the world beyond the Ivy Tower are needed. And a school like the University of Chicago doesn’t need to worry about diluting academic rigor. Universities are increasingly bringing in practitioners.

You teach at Yale, yet you don’t have a degree beyond your one from Chicago. Does that serve a similar purpose?

Yes. Yale brings in people like me who do not have PhDs and [retired Amy General] Stan McChrystal and former diplomats to teach. As long as we take academics seriously, we bring in real-world experience and presumably that counts for something. We don’t have research agendas. We find teaching fun. We just want to spend time around students.

In a column from last month titled “Love and Merit,” you wrote about what you called “directional love” that parents shower on their children so long as they perform brilliantly (i.e. get into a prestigious college, take first prize in the cello competition, etc.). If they don’t bring home these prizes that reflect well on the parents, the love dries up. A few days before that column was published, in an interview with Politico, you estimated “20 percent of your Yale students as suffering from this syndrome.”  What kind of feedback did you get in class?

I haven’t been back since I wrote that column. I’ve been on book tour. But I riff on this many times with my students. Some experienced it, some have not.

Do you find similarities in the characters of your Yale students and the students you talk to from the University of Chicago?

I’m amazed by how different students are at the U. of C. Same talent pool as Yale and Stanford and Harvard and Princeton and Columbia. Each school has a distinct personality. At the U of C, students are remarkably intellectually original. Harvard students are professional, groomed more to go into consulting and [investment] banking, but something about the intensity of Chicago’s Common Core curriculum breeds a different kind of person. More intellectually spicy.

In the wake of the terrible financial problems facing Chicago, what do you make of the comparison of Chicago to Detroit?

It’s completely wrong, or at least 70 percent wrong. Chicago has the Commercial Club, the Commonwealth Club, the Community Trust, stronger civic institutions, and stronger commitment to the city than any city in the country. There are a lot more people working on stuff to make the city better; a vibrant art scene, strong commercially and culturally. Some big Midwestern cities are struggling—Detroit and even Cleveland—while Chicago and Minneapolis have thrived. Education institutions play a large role. [Brooks clarifies he’s talking about higher education, not CPS.]