It's almost embarrassing how many "L"s this guy takes.

So you’re a New England Patriots fan and you love Tom Brady — it must be an embarassing smudge in your life, knowing full well your fervent support is for one of the biggest losers in NFL history. Not only does he bear the great burden of being in the top 1 percent of money owners in the world, but he also flies all the time in dangerous jets and has to sit through dinners with his tie pulled all the way to the top button. If he isn't one of the finest examples of failure, then we're not sure exactly who is. Just look at the bullshit he has to go through on the day-to-day, proving why he's such a loser …

Because of his stupid perfect teeth

Do you even chew, bro? It’s widely known by everyone that having perfect teeth is a firm sign of being a non-adventurous square. Lacking that fine layer of protective enamel means you hit the bottle often with best friends, drink a go-getter's portion of coffee every morning, and have likely been in at least one drunken scrum late night at the bar — like what normal people do. Clearly, Brady’s social life is sub-par.
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Because he’s married to Gisele

Wonderful, another familiar tale about the popular high school kid hooking up with a supermodel, can it be any more monotonous? He couldn’t have gone for the nerdy scientist or curvy drama-club president? Dinner conversation with these two has to be the most tiresome banter in history:

“G’day Tom, what fancy you today?”
“Oh Gisele, I practiced my throwing form in the mirror again. I’m so beautiful.”
“Aye peaches, can you please pass the money shaker for my gold toast, dear?”
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Because of his dumb diet

For whatever reason, Tom Brady and Gisele Bündchen’s diet was the only thing hitting headlines for a solid few days a couple of weeks ago — a ridiculous empty-space that includes the two never cooking with olive oil, avoiding tomatoes, eating only “organic” foods and living sans any true pleasure of life like caffeine or cheese. The strict regimen likely ensures he’s one of the healthier men on the planet right now. *cough* one-upper *cough*
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Because he fought the law, and won

Deflategate was inarguably the most important story of the last seven or eight decades in American history. No other moment in time was more enthralling, more significant to the way the stroke of cultural stain would brush upon the canvas of the future. But because he won, Brady willingly accepted his allegiance to privilege wrapped in a perfect blanket of elitist defeat. He was even allowed to undo his four game suspension penalty. It's a long way down to fall from that ivory pedestal.
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Because of his stupid sexy haircuts

Presenting exhibit 1 – 9. That is all.
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Because he has all of that money

In the exact words of one of the most prominent and honest men in music, “Mo money, mo problems.” Like, could you even imagine doing taxes at the end of the year for a person like Tom Brady? He doesn’t even qualify for the Earned Income Credit, which essentially puts free money into your pocket for being poor. FREE MONEY!
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Because he spends quality time with his children

Actually, no, this is pretty fucking cool. Great work, Tommy.
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Because he only has four Super Bowl rings

What an idiot! Most people have 5 fingers on each hand, not 4. Does he think he can just hide his thumb and people won’t notice that it’s completely void of a 5th championship adornment? Stupid Brady can’t even count he’s such a failure.