Photo: Courtesy of Fox News

Eric Bolling, 53, one of five hosts of Fox News’s The Five, grew up in Chicago and attended Queen of All Saints School and Wilmette’s Loyola Academy. Watching him a few years ago as he substitute-hosted for Bill O’Reilly, he described growing up poor in Sauganash. It stuck with me, and so did his fulsome support of Donald Trump, from the day in June 2015 when he first descended the Trump Tower elevator to announce his run for the Republican nomination.

I had written recently about his colleague Megyn Kelly and her years in Chicago, and decided to seek an interview with Bolling. His regular co-hosts are Dana Perino, Kimberly Guilfoyle, Greg Gutfeld, and Juan Williams. Before Fox, he was also, briefly, a professional baseball player, and, for 15 years, a commodities trader and executive.

We spoke by telephone for an hour last Wednesday.

There’s been much speculation that Trump was going to offer you a position in his cabinet—commerce, I read. What happened?

Donald Trump has been my friend for many years, and obviously if you watch Fox News, [you know] I’ve been pro-Trump for a long time. They called me over to Trump Tower to ask if I’d be interested. I said, “Thank you very much. I’ve been a proud supporter of yours, but I love my job.” There was some talk of commerce secretary but it was rejected by me.

They wanted you to take the lead job that went eventually to [billionaire businessman] Wilbur Ross? Or was it the deputy secretary’s job?

I don’t know. The way transitions work is a number of people are floated for jobs and then they whittle them down. It may have been just a float to test my level of interest. [The job of deputy commerce secretary went to Chicago Cubs co-owner Todd Ricketts, whose family worked against Trump before working for him.]

How did you meet Trump?

About 15 years ago, a good friend of mine, Mark Burnett, was producing The Apprentice program. And he brought me to some Apprentice events and Donald Trump was present and we just got to talking to each other quite a bit, and I had a Wall Street past and knew business very well, and he appreciated that and over the years he invited me to various events.

You were a supporter from the get-go?

When he came down the escalator with Melania at Trump Tower, I noticed that every single eyeball across the newsroom, people calling each other and saying, “Do you see what is going on?” And I realized he is tapping into some emotion, whether you liked him or disliked him, he was still able to tap into an emotion that other candidates were not able to do. And I said, this guy is my friend and he’s going to be the next president. Here we are, he is.

Are you satisfied with his cabinet picks? Any misgivings? If yes, who are the misgivings?

Rex Tillerson [Exxon C.E.O. chosen for secretary of state] is a wonderful pick. We’re fortunate to have someone as diplomatic, as well-versed in countries around the world as Rex Tillerson. It’s amazing we can put these successful people in a cabinet where they’re going to make one-tenth or one-one-hundredth of what they’d normally make in business.


I don’t know why Mitt Romney was even floated for secretary of state, but I’m glad Mr. Trump picked Rex Tillerson.

What about the criticism that Trump has selected too many generals?

Oh gosh, I’m in the camp that there could never be too many generals. These are the adults in the room. These are people who have world, life experience, people who make decisions that affect people’s freedoms and lives. And, by the way, the generals he picked are not necessarily pro-war or interventionist. Some of them pushed back on intervening in the Middle East conflict.

Trump has been critical of Federal Reserve head Janet Yellen. Who would you like to see replace her?

I’m not going to get into the Fed—it’s supposed to be apolitical—but I will say that I think [JP Morgan Chase chairman] Jamie Dimon would be fantastic at Treasury. But that’s just not going to happen. He has too much invested. He wouldn’t leave.

So you’re not happy with the pick [Steven Mnuchin] that Trump made?

I’m not unhappy with it. I also like Michael Bloomberg. I think the new administration is going to be all about business, commerce and the economy.

What about the Supreme Court? Someone you have in mind?

Ted Cruz. I’d like to see him fill Justice Scalia’s seat.

On Election Day, the consensus was that Hillary would win. What were you thinking?

I said he’s going to do it. People thought I was crazy, I mean crazy. They called me names I wouldn’t even want to repeat. That night at 11:20, we did a hit on the election. Now let me just preface this, throughout this thing, I eat, drink and sleep the numbers; I have an affinity for numbers. I knew exactly what Donald Trump needed to do. Going into that night, he had locked down all the states he was expected to lock down. While we were on air, Fox called Wisconsin for Donald Trump. That’s 10 electoral votes. He needed 16 to get it done. While we’re doing that hit, Fox called Iowa, six votes. That was the 16 he needed. That would have been 269, tie, we would have won with a tiebreaker. So I knew it was happening. I called it on air before anyone called it.

You were ridiculed by your own colleagues on The Five during the campaign for describing Trump’s rally crowds as enormous and Hillary’s as small and linking that to a Trump win. Your mantra was “crowd size matters.”

The polls were saying something different and I kept saying, don’t listen to the polls, listen to the people. A lot of people coming off these rallies weren’t your typical voter. These are people who might not have voted in years. They saw something in Trump that they liked. They saw an outsider, saw someone who spoke for them.

You grew up in Sauganash. Was your dad a cop or a fireman?

My father was a traveling salesman and my mother sold women’s coats at Marshall Fields. We didn’t have much money. I was seven years old, when my mom took me to shop for clothes in a little neighborhood store. I picked up Pro-Keds, and she looked at me and said, “We can’t afford those. Can we pick another pair?” That was my first understanding of have and have not and we were clearly the have not. I saw the pain and sadness on her face when she told me that. And it was that moment that I thought I gotta make this better for us, for my family, for me. And I worked hard. People call me the hardest working guy in baseball and then the hardest working guy in commodities, my next career, and now the hardest working guy in TV.

I grew up in West Rogers Park where almost everyone was Jewish so there were very few Christmas decorations. On Christmas Eve my parents would drive us to Sauganash to gawk at the huge houses and the elaborate Christmas decorations.

We didn’t have the beautiful lights on our house at Christmastime. Let me explain why we were poor but lived in Sauganash. My mother’s father was a builder, but his company failed. He built exactly two homes. They went bankrupt and there were two tiny homes and we lived in one of them. This was one of the most difficult things for me growing up, being poor in a wealthy neighborhood. I was an outsider and let me tell you something; those kids let me know it.

I’ve heard that you’re such a devout Catholic you go to mass every day.

I go to St. Patrick’s Cathedral every day to light candles, five days a week. I don’t necessarily go to mass, but if there’s a mass there, I’ll stay for it I go to mass every Sunday with my wife, so six days a week I’m in church.

How did you end up being recruited out of college by the Pittsburgh Pirates [as a third baseman]?

One thing that equalized everything was sports, and I was a good baseball player. On the field it didn’t matter if you were rich or poor. I did very well at Loyola Academy and then I got a scholarship to Rollins College in Florida and in senior year the Pittsburgh Pirates came to dedicate our new stadium. Seats were filled with a lot of scouts. I hit a home run on my first at bat and they drafted me that year. I was only there for a portion of the first year because I ended up blowing my rotator cuff out. I was 22.

Is that a career-ending injury?

Branch Rickey Jr., who was general manager of the minor league system for the Pirates, called me in. “Look, we’re not going to rehab your shoulder.”  I had nowhere to go and nothing to do and I went back to Chicago, started knocking on doors to find a job. My father saw me moping around for a few days and he circled a classified and said, “Go out and see if you can get this job.” The casting call was at the Hyatt at O’Hare, and I went out and it was snowing like crazy and there were 200, 300, 500 people there, and we were all applying for five jobs, and they ended up being marketing jobs for Mobil Oil and I got one of the five.

I was basically a traveling salesman like my father. I was a marketing rep, which means I’m in my car driving around to different gas stations, trying to help them market their gasoline. A friend of mine’s father was an oil trader and I went up to Boston. I worked there for a while and I realized the real money was on the trading floor at the New York Mercantile Exchange.

So one day I prepared resumes, went to the New York Merc’s exchange floor, handed out resumes, and got a job. I worked for a long time for a guy as a runner, but made no money. I borrowed money from other traders because they liked me. I put myself into the trading pit, and that was start of a trading career culminating with my being on the board of directors of that exchange. I also helped bring the exchange public.

Growing up, you were a Cubs fan?

I had a red Schwinn with a banana seat and we used to ride straight to Wrigley, from Sauganash, though we didn’t have money for tickets. We’d hang out outside. Every once in a while, a ball would go flying over the left field wall and you’d go chasing, fighting for a ball. I’m not sure I ever got one, but it was some of the greatest times of my life.

If Trump doesn’t adhere to his promises about the Muslim ban or the Mexican wall—he has already walked back his pledge to bring charges against Hillary Clinton—does it matter?

He has adjusted his ban on all Muslims to extreme vetting from areas that have high incidences of terror. As for the wall, I would bet my bottom dollar that there will be a wall built, not a fence, but a wall. You can’t make these promises and have this much success based on the promise of the wall and then not do it. I’ve given Donald Trump ideas, on air, about how to make Mexico pay for the wall. I’m in favor of him continuing the wall project. It’s also a good way to hire and employ a lot of people.

Laura Ingraham, a Fox regular, is being talked about as Trump’s press secretary. Are you for that?

She’s a very good friend of mine. I think she’s extremely talented. She would be a huge asset to the Trump administration if she could be in some policy position [rather than press secretary]. I hope she does join the team, but she’s a very successful radio host and she has a website, and that’s a big ask to leave all that for the service of the country.

Do you follow Chicago politics and read our newspapers?

Not closely, no. I do follow when Chicago makes news for crime. I’m unabashedly conservative and I think what Chicago needs is a good conservative mayor. You have to embrace your law enforcement. They don’t seem to be doing that there, or in New York, for that matter.

You don’t like New York Mayor Bill deBlasio?

I think he’s the worst mayor, at least in my lifetime, in this city or any city I’ve been in. [Bolling lives in Bergen County, New Jersey.]