Politicians Suck at Wearing Baseball Hats – I Examine Why

I’m going to borrow one of President Obama’s favorite verbal tics and open with this statement: let me be perfectly clear, this is NOT a feature about politics or policy or politicians’ policies. It’s about baseball hats.

I don’t care what you think politically and I’m confident you don’t care what I think. What I’m concerned with here is the disturbing and overwhelming inability of politicians to have a single, well-worn, comfortable-fitting, non-free giveaway at the ballpark by a credit card company-looking baseball hat.

I mean, what the hell?

I love hats. I wear them to death and then keep wearing them:


So I say this with all sincerity: It is of no consequence to me if Donald Trump has made a billion dollars or lost ten billion, he can certainly do better than this thing wreaking havoc on his head:


Stare at that red monstrosity for a second. It looks like it was folded up and vacuum sealed at the bottom of a box of Cracker Jack and then opened the day of this photo. The brim is all uneven and screwed up. The front is still pointed and has that billboard look and it’s all puffy and wrinkled as it goes around his head. It’s a disaster.

The Donald has owned/owns dozens of businesses involved in apparel… And he couldn’t find a decent company to make a strong hat? Sad.

And just because Hillary is a women doesn’t mean she’s off the hook. Some women can pull off hats. Others can’t. Hillary falls into the second category. I know there are hair issues and blah blah blah… And forget for a moment that she’s wearing a Cubs hat in this older picture… But couldn’t someone have found one that actually fit? The hat even covers her giant sunglasses and would probably be too big for Bubba, who has a large dome for sure.


Then again, Hillary doesn’t have a shot of looking good in a hat if she’s relying on her husband for advice. Bill Clinton looked categorically absurd almost every single time he donned a baseball hat. Each time it looked liked he took it directly off of a homeless person’s head:


Or that he got it in the mail after cutting out 10 UPC labels from his Fruit Roll-up boxes and sending them back for a prize:


Are you kidding me? Someone in Clinton’s cabinet or part of his PR team saw this hat and said, “Yes, Mr. President, Mr. Leader of the Free World, you should wear this. It’ll look great.”

If I’m president, the person who hands me that hat is fired on the spot. No questions asked. Even if Smokey the Bear is on the lid, I’d expect a White House aide or staffer to wear it for a few weeks to break it in for me. Don’t give me any of this right-out-of-the-box crap.

So maybe you’re thinking, “Jon, these Clinton photos are from 10+ years ago… Cut these politicians a little slack. They weren’t as hip as politicians are now to appearances and looking cool. They weren’t politicians in their prime in the age of Instagram and Twitter and Facebook.”

To that I say, it makes no difference when it comes to politicians and hats whatsoever. Case in point: our current president and last vice presidential candidate.

In the annals of goofy-looking, ill-advised hats and photo shoots, this Paul Ryan get-up might be the hands down winner for worst idea ever:


Forget that perplexed, befuddled look on his face… Let’s focus on that travesty of a hat on his head. Cloth straps? Really? You gotta go fitted or at least the cool old-school snaps or thin velcro… But a cloth buckle? Duuuude. And the hat is also huge. Way too big for his head… This thing screams dork louder than if he actually shouted, “I’m a huge freaking dork!” into a megaphone.

And backwards? C’mon, man. You can either pull off a backwards hat or you can’t. You just have to know these things about yourself. It’s part of becoming a man and knowing your own style and look.

If you’re going to wear the hat backwards, then your goal is to try and look cool and relaxed and easy-going and confident. The Godfather of the backwards hat is Ken Griffey Jr. He owned it. He popularized it. He’s the king. And to borrow an old political line, you, Paul Ryan, are no Ken Griffey Jr.:


Holy crap, he looks amazing. I loved Junior. That’s how it’s done, man.

This, Mr. President, is not how it’s done:


Did your grandfather give you that hat and put it on after messing with your hair and pinching your cheek? Not a good look, Barry. Not. A. Good. Look.

But you do slightly better with it facing forward, I will give you credit here:


This hat actually looks like you’ve worn it before and it generally fits well on your head. Nice work, considering the company you’re in.

Your predecessor wasn’t bad in the hat game either… To be fair, he owned a baseball team and if he couldn’t pull off a hat, well… That’s the easiest part of the job:


But don’t worry, guys. None of you will ever wear a hat less broken in and more ill-fitting than fake-Red Sox fan John Kerry:



John lost all credibility with me when he refused to talk about the Red Sox / Yankees rivalry at a Sox game and instead opted for a line about how New York has great people too… Loser… And whenever he put on a Sox hat it looked like his staff forgot he didn’t actually own one, so they went to CVS and grabbed the shittiest one they could find near the cash register next to the Almond Joys, and bought it for him to wear. This one sits atop his head like it was taken off an elderly woman on the T and he didn’t feel like readjusting it.

But never fear. It’s only the second worst Red Sox hat I’ve seen worn by a famous person.

What’s number one?

Tom Cruise in A Few Good Men.



This is from one of my top 5 movies ever…and the Sox are my team…and I love almost all Cruise’s movies…and he’s not a politician… but I will never get over what Tommy did to this hat, which we are to believe Lt. Caffey wore playing softball all the time.

The costume designer was clearly absent the day they taught costume design at costume design school.*

By: Jon Finkel

If you enjoyed this post, you will absolutely love my book, Jocks In Chief, where I rank every single president by their athletic ability. Buy it HERE.

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*If you get this line then we should be best friends.

Jon Finkel is the author of Forces of Character with 3x Super Bowl Champion and Fighter Pilot, Chad Hennings, Heart Over Height with 3x NBA Slam Dunk Champion Nate Robinson, as well as Jocks In Chief, The Dadvantage, and all twelve volumes in the Greatest Stars of the NBA book series for the National Basketball Association, which won several ALA Young Reader Awards.

As a feature writer, he has written for Men’s Health, Men’s Fitness, Muscle & Fitness, GQ, Details, The New York Times, AskMen.com, ComedyCentral.com, Yahoo! Sports’ ThePostGame.com and many more. His work received a notable mention in the 2015 Best American Sports Writing anthology. He has appeared on CBS: This Morning promoting his books.

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