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A Tale of Two Millennials: Pajama Boy and Me

Pajama Boy and I went to the same High School. How did two Millennials from the same place end up so different?

I was in no way surprised to learn that the young man we have come to know as “Pajama Boy” went to my high school. Ethan Krupp – the Onesie-clad gentleman chosen by Organizing for Action to be the face of their “Get Talking” campaign – also graduated from New Trier Township High School. But the similarities between us don’t end there.  We are both in that 18-35 “Millennials” demo that everyone loves to talk about. We both wear glasses. We are both politically and culturally active.

And we both want our generation’s attention (on behalf of very different values).

New Trier is a public high school located a few blocks from Lake Michigan in Winnetka, IL. The list of her prestigious alumni includes the likes of Charlton Heston, Donald Rumsfeld, Rock Hudson, and Rahm Emanuel. Many of Chicago’s most important and influential families live in the suburbs directly north of the Windy City. There’s a lot of money, a lot of influence and a lot of white guilt.

Now, I do not personally know Ethan Krupp. I do not wish him any ill will. I had no pressing interest in his background until I learned that we graduated from the same high school. My purpose today is simply to flesh out the stark contrast in worldviews between a young conservative and the wealthy liberals he grew up around.

One of the most prevailing (and harmful) myths in our society is that people with money are monolithically conservative Republicans who would turn out Bob Cratchit and Tiny Tim if it meant adding a farthing to their unfairly earned fortune. In my experience, this is an incorrect and misleading caricature on multiple levels.

The 1% of the 1% sent their kids to my high school. The typical parents of a New Trier student were folks who had attended prestigious universities. They were CEO’s, world-class lawyers or, as we used to joke, the descendants of Mr. Soldier Field. Each morning a fleet of Range Rovers and BMW’s delivered expensively clad students to the front steps of our school. We excelled at sports like tennis, soccer and lacrosse. We had a Badminton and Fencing team.

But we also had the first LGBTQ club in the state of Illinois. We also heard more than our fair share of “social justice” preached via educators and after school clubs. Our teachers and administrators were model examples of the proud (and vocal) brand of “progressive” one encounters in the public education systems around the country. And when these privileged kids went off to schools like Denison, Brown or Stanford, their journey to cultural, political and economic liberalism was a short one.

Please understand that I loved attending New Trier and still miss living in that luxurious section of the Chicagoland area. My father happened to be hired as a pastor at a church within the school district’s limits. We lived in the church’s parsonage. We drove used cars. I worked as a caddy and umpire – Big Blue, they called me – in the summers to pay for stuff like new football cleats come fall. It was a wonderful existence and I found some great friends (from the families of varied tax brackets).

Because I had parents who practiced the command in Leviticus to show favoritism neither to the rich nor the poor, I avoided growing bitter of the extreme wealth and power that surrounded (and largely eluded) us.

The lesson I learned from those years spent among Chicago’s elite was this: it’s the values, stupid.

Everything comes down to your beliefs and core convictions. It’s about worldview, not the kind of cars parked in your garage. A lot of kids from my high school saw the affluence and influence wielded by their families, but never had the benefit of someone explaining to them how to properly think about and use such blessings. Even fewer were equipped with a proper appreciation of how exactly their parents’ money was made and the entrepreneurial spirit that powers the engine of America’s economic growth.

Someone like Pajama Boy ended up the poster boy for massive wealth redistribution and government intervention into the personal lives of its citizens after being raised in a privileged environment populated by people who reject such naïve, idealistic notions in the practice of their everyday lives and careers. Very few successful people can afford to actually “live out” liberalism’s fiscal policies. The math doesn’t add up.

This “suburban guilt” that so many Millennials feel is, in part, the result of a battle between the inherent Judeo-Christian altruism we imprint on the hearts and minds of our kids, and some combination of parental hand-washing when it comes to the duties of passing on values to your children and the progressive indoctrination drilled into them at institutions such as New Trier High School and the University of Wisconsin-Madison.

I don’t know Pajama Boy’s ideological testimony, but I saw first-hand how easily the 1% in this country can end up supporting policies that had little bearing on the course of their own family’s success. So while I will not question Pajama Boy’s motives, I cannot avoid questioning his judgment.

Follow R.J. Moeller on Twitter.

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