I Made Angry Cops Join the Air National Guard Over a Super Bowl Bet

Super Bowl Sunday is a day of parties, drinking, and chicken wings for most Americans. For me, it’s a day I gamble on a sport I don’t follow (nor care about) and craft an extremely creative wager with whoever is dumb enough to agree.

Some of you may remember a few years back when I wagered a “perm” when the Atlanta Falcons took on the New England Patriots in Super Bowl LI. At halftime, the Falcons were up 28-3, and I had accepted the inevitable: I would be honoring my bet and getting a perm. To say I was surprised when I woke up the next morning and learned that I had actually won is an understatement. And that is how the crazy Super Bowl bet nonsense began. 

Fast-forward a few years, and the taste of victory is as sweet as it’s ever been. Especially when you know one of your best friends — or mortal enemies (whichever day it is) — is forced to come to terms with a life-changing wager he made. Over a football game.

It all started when Richard Hy, better known as Angry Cops, stopped in San Antonio for a quick Free Range American podcast last month. He was the perfect target, someone who would let his emotional machismo cloud his good judgment and accept a high-stakes wager with me on the upcoming game. 

I posed the possibility of a bet in the middle of the show. Richard was dead set on making me hurt. Physically hurt. He suggested that if I lost, I would be required to attempt a full marathon with little to no train-up. He also added that he would like to be in a human-powered buggy the entire race following me, shouting at me while relaxing and enjoying a few drinks. While I ran myself to literal (probably) death. 

Well, for stakes of that magnitude, I needed something really good. If there’s one thing everyone knows about Richard, it’s that he has based his entire internet persona on him being a big scary US Army drill sergeant. I could think of no better way to take his ego down a few pegs than hitting him where it hurts: his pride. 

So I countered his death-by-run wager with a proposition that, if he lost, he would have to direct branch transfer from the US Army National Guard to the US Air National Guard. Big scary Drill Sergeant Hy would have to “Aim High” and “cross into the blue” and turn into Airman Hy. 

To my surprise he accepted the wager. He took the Chiefs as his team, which left me rooting for Brady and the Bucs. Both of us anxiously waited for the Big Game to arrive. 

The day was almost upon us, but in the aftermath of a recent Air Force social media misstep, the landscape had changed a bit. A week prior, the Chief Master Sergeant of the Air Force dragged the reputation of an active-duty Pararescueman through the mud on Facebook, and we all knew Richard’s temper was not going to let that slide.  

So he did what any other military influencer would do, and made an eloquent rant video targeting the CMSAF. “[Bass] just skull-dragged his reputation through the mud by re-posting an article that she never fucking verified?” Richard said, referring to the Air Force “PJ” affected by the social media post. “Where is your social media team on this? Did you read the article before you posted it?” 

Being the thoughtful person I am, I decided to text Mr. Angry Cops and suggest we modify our wager, seeing how allowing him to enlist in the US Air Force would be pure suicide on his part after the vitriol he had just leveled at the most senior enlisted leader in the entire branch. And no, this had absolutely nothing to do with me trying to escape 26.2 miles of hell. 

Actually, it 100% did, but he gave me a way to escape this madness and I was going to exploit it with every angle I had. 

We chatted on a FaceTime call and set new terms for the bet and they were as follows: The participants will don their “Mess Dress” uniforms and meet in downtown Austin, Texas. The loser will take the podium and begin a 10- to 15-minute concession speech authored by the winner. The loser will present the winner a medal, and finally sing the winner’s Service Song. 

We both nodded in full agreement and waited for kickoff. 

Now here we are two days after the carnage has settled. The Bucs were victorious, which, whatever, the important thing is that I don’t need to run a marathon now. Richard spent a whole day not speaking to me, and then to my surprise, texted me the above image at 11:13 a.m. EST with the following: 

“A Bet is a Bet. I will Honor all terms set and see you in Austin next month. Now excuse me, I have to go buy uniform tapes that say US Air Force.” 

I almost cried. What an absolute legendary move on his part. I cannot wait to see how much his military career flourishes, or goes down in flames now that he has crossed into the blue.