Working Class Man Sneaks Into Wealthy Society, What Happens Might Shock You

What happens when a working-class man finds himself rubbing elbows with the elites?

*NOTE: Names and identities have been withheld to protect national security … and secrets that are best left in the dark.*

As OutKick readers know, I come from very humble roots in rural Wisconsin. Specifically, I grew up in Randolph before spending some time in Montana in my younger years.

We didn't grow up with much. We had to scrape and claw for everything in life. There was nothing guaranteed, and when you grow up that way, you grow up fast and you grow up tough.

I don't run from it. I'm a working-class man who would likely be shot if I attempted to enter a nice country club. So, what happens when I manage to sneak into a group of elites?

*EMAIL ME REACTIONS AT DAVID.HOOKSTEAD@OUTKICK.COM*

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What happens when a working-class man visits high society?

I was sitting at a bar in Arlington, Virginia the other day after needing to leave Hookstead Compound (location classified) for some remodeling.

My phone buzzed to life and a close friend of mine had a simple question:

Do I want to attend the Virginia Gold Cup on Saturday?

For those of you who don't know, the Virginia Gold Cup is a super-fancy horse racing event at a massive and sprawling place in Virginia. It runs races throughout the day leading into the Kentucky Derby.

Honestly, I was a bit hesitant. Was this a mistake? Was I really being invited to an event where I would almost certainly be the poorest person there? It wasn't a mistake. I was forwarded some tickets, arranged transport for Saturday and I assembled a crew consisting of myself, my fiancée and two friends whose names can't be revealed for too many reasons to explain.

This was really happening. I was finally going to get a taste of the high life. I was finally going to get to know what it was like to be around some of the most powerful people in politics, finance and media.

Not too bad for a small kid from rural Randolph, Wisconsin. Prior to leaving, I had to start the day with a coffee.

My favorite Wisconsin Badgers mug. (Credit: David Hookstead)

Then, I had to find a suit to make sure that I wasn't immediately sniffed out for being a blue-collar man and not a multi-millionaire.

This was the vibe I opted for.

A look at my outfit for the Virginia Gold Cup. (Credit: David Hookstead)

We piled into a car being driven by one of the most powerful women in media, but the air-conditioning situation was….lacking.

Yet, after growing up with my tough roots, I'm not one to complain. I immediately put on "Courtesy of the Red, White and Blue" along with many other great hits.

We were vibing the whole ride there.

Now, it's important to note I've never been to a horse racing event before. I have no idea what to expect. I'm going in totally blind, but I'm not nervous.

I'm at my best when the bullets are flying. I wouldn't have it any other way. If you're going to live this life, you might as well charge forward into uncharted territory.

That's exactly the moment I found myself in. We navigate to the private area of the party, and I immediately see enough influence and power that we might decide right on the spot whether or not we're going to bomb Iran.

I'm not even kidding. The topic was discussed at length, and we ultimately all decided the diplomatic option is the best option. I'm a little stunned by the fact I'm even here.

It was a bit hot, and I had to ditch my jacket. (Credit: David Hookstead)

Here's a kid from the rural countryside of Wisconsin, and all of a sudden, I'm in the same area as people whose life stories might be too much for even Hollywood.

What a truly bizarre and *AWESOME* experience I find myself having. I also discovered the tasty beer below. I might have had more than one. Sorry, mom.

A look at the beer I was enjoying. (Credit: David Hookstead)

Now, having a hat is a big part of the game when it comes to high society events. I'm totally unprepared. I do not have a hat of any kind, and I'm starting to stand out a bit.

Fortunately, I was able to get my hands on an Indiana Jones-style hat, and I'm not going to lie, I looked awesome in it.

A look at the hat I wore during the Virginia Gold Cup. Second person's identity redacted for national security reasons. (Credit: David Hookstead)

Despite the fact that I grew up in a setting where Culver's was fine dining to me (best burger in all of America!), I find myself fitting in shockingly well. We're talking about war, politics, media, the economy and everything else you can imagine…..and it's happening with people way smarter than me. As they say, if you're the smartest person in a room, then it's time to find a new room.

The fiancée is also having a great time, which is always a positive.

My fiancée definitely enjoyed her time at the Virginia Gold Cup. (Credit: David Hookstead)

Now, I also have to admit that I didn't spend any time watching the horse races. The conversations were far too interesting and captivating.

I brought a wad of working-class money to put some bets down, and didn't even manage to place a single one. It was simply not worth taking a single break or moment away from the situation I was in.

Another look at my awesome hat at the Virginia Gold Cup. Identities of other individuals redacted for national security purposes. (Credit: David Hookstead)

I also ran into a handful of people from a different part of my life that feels like a lifetime ago. You know that feeling when you see someone again, and without having to say a word, the memories of what you all went through rush back? It was like that every 30 minutes or so. It was a constant reminder of the trenches of the grind, and all the people who were there with me doing absolutely insane things in and out of media over the course of more than a decade.

It was surreal seeing where people have gone, looking back at what we did back in the day and much more. Those stories, for now, are best left in the dark. Some sleeping dogs are best left alone.

A look at my time at the Virginia Gold Cup. (Credit: David Hookstead)

We ended the day at Ragtime in Arlington, and a topic that I rarely discuss comes up:

The Mississippi Miracle.

The Mississippi Miracle (not the name I gave it) refers to an old incident in Oxford, Mississippi that would put any Tom Clancy book to shame. One of the people with us had never heard about what happened in those early morning hours nearly a decade ago.

I share the story, and she hangs on every word. As I've said before, I'll share it someday when I'm older and everyone is out of their government roles, but that day is not today.

I had a blast at the Virginia Gold Cup. (Credit: David Hookstead)

It turns out that a working-class guy like myself can manage to fit in with even the most elite members of society. They might have much bigger bank accounts, but I'd like to think we all have a lot of heart. It goes to show anything is possible in life. Let me know what you think at David.Hookstead@outkick.com.

*Parts of the day have been redacted to conceal information about the guest list, activities and people with security clearances.*