15 Funny Brady Family Pictures

When you match the greatest QB of this era and the most popular super model in the world, you’re bound to get some media attention. Thanks to the paparazzi and various other photos, we’ve gotten a slew of some of the most awkward Brady family photos in the last couple of years.

In this article, we go way back taking a look at bizarre photos of Brady as a child; we’ll also dive into Gisele’s life before she met Brady - she had quite the dating resume before meeting Tom, you’ll get a glimpse of that on this list.

Whether it be dressing like a piece of toast and avocado together on Halloween or Gisele chugging down red wine in the press box just days ago with her daughter on her lap at the Super Bowl, these are some of the most awkward Brady family photos both from the past and present. If you need a good laugh, then this article is for you. Although Tom and Gisele seem like perfectly normal humans on the surface, this article is going to tell you otherwise. Enjoy and like always, be sure to share the article with a friend. Without further ado, here are 15 awkward photos of the Brady family. Let’s get started!

16 Gisele Chugging Red Wine At Super Bowl

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During the recent Super Bowl we got to see several viral moments, one that included Twitter blowing up over a shot of Gisele chugging some red wine when the cameras got a glimpse of Brady’s wife. We tend to forget, but such a game can be just as stressful on the family members of the participants and that surely includes Gisele. When the cameras were briefly on her, she had her five year old Vivian sitting on her lap while she pounded down some red wine, not a bad way to calm yourself down during such a game. The awkward moment made the rounds online of course.

To Gisele’s credit, she was graceful in defeat this time around, though as you’ll see a little later, that wasn’t always the case.

15 Tom’s Awkward Camera

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Although he might be the greatest quarterback of all-time, that doesn’t mean Tom Brady isn’t a bit of a weird dude in his everyday life, you’ll see countless examples of that throughout this article. This particular incident, might be one of his most awkward however as he attached a camera to a “Not So PG” area, of course, the photo went absolutely viral with fans wanting answers for the disturbing attachment position.

Turns out, he was shooting a commercial for UGG’s and thankfully, he wasn’t alone as his dog also took part in the shoot. At the very least, it does help the situation significantly, though at the end of the day, it’ll always be remembered as one of Brady’s most awkward photos and one he likely wishes the paparazzi didn’t catch.

14 Gisele Disguised In A Burqa

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Just a couple of years ago in 2015, Brady’s wife made the headlines for all the wrong reasons. In visiting Paris, Gisele opted to get a certain surgery done on her breasts and eyes, though she wanted to keep the procedure on the down low. Oh what a mistake that was as the story blew up even greater than in should have.

Gisele was spotted rocking a Burqa as a disguise, the Muslim community was outraged at the outfit. Things would only get worse as Gisele’s surgery information was leaked and it was deemed to cost a grand total of $11, 000. It was an awkward moment that seriously couldn’t have played out any worse for the former Victoria Secret model. We thank the paparazzi for providing us with such an awkward moment.

13 Tom’s Younger Days

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Let’s face it, Tom Brady’s one good looking dude. Even if you dislike the guy, you can’t deny that he’s got a certain charm about him. One would assume he was a great looking dude his entire life, though, in an awkward twist, the photo above proves that this wasn’t the case during his youth.

Brady grew up alongside three siblings, all girls. He was a huge fan of multiple sports growing up; he followed football and basketball religiously along with taking a liking for baseball. He played both football and baseball during his high school days - as you see in the awkward photo above, one would never assume this kid would turn into the greatest QB of all-time (or at least arguably). He would eventually opt to give up baseball and pursue football full-time – a decision we can admit has worked out quite well.

12 Gisele Rides ATV With Unprotected Baby

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When you’re a world famous model and married to one of the most popular athletes in the world, you can guarantee the paparazzi will do their best to track down your every move along with criticizing some of the things you do. Well, in this awkward photo, that’s exactly what transpired as Gisele was photographed while riding an ATV overseas.

The photo was snapped during January of 2014. Gisele was enjoying a Costa Rica trip alongside her daughter Vivian. One photo in particular made the rounds as Gisele rode on an ATV while leaving her daughter was unprotected with a helmet, the photo caught the attention of several news outlets and again, it was made a bigger deal than it really should have been. The photo was as awkward as awkward can be, it seriously looks like Bundchen stole a baby and drove off on an ATV.

11 Brady’s Ex & Current Wife

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Before Gisele was in the picture, Brady dated Bridget Moynahan, a model and actress. The two dated for a couple years from 2004 till 2006. Normally, such a relationship wouldn’t have such an impact, though the birth of Tom’s son from the relationship made the story a huge deal.

Right when the couple broke up, Bridget gave birth to Tom’s son, John Edward Thomas. He would start dating Gisele in 2006, even before the birth of his kid making the entire situation truly an awkward one. Adding to the chaos, the paparazzi sniped a perfect photo of the three altogether (along with Tom's son), a moment you would assume that was extremely awkward. However, it might have only been awkward for us watching as Gisele and Bridget even closed out their conversation with a hug - yup, that’s awkward.

10 The Avocado & Toast Costume

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You’ve got to give Brady some credit, he’s rocked some awful costumes in the past just so he can match with his wife Gisele. His wife is a big advocate for plant based diets, given her love for keeping it animal friendly she decided to rock this hilarious costume that could have only been complete with Tom's assistance.

The two dressed up as toast and avocado.... it was one of the most awkward yet hilarious couple costumes we’d ever seen a popular couple wear. Although it was bizarre, give the couple some credit for having a sense of humor on the day and not wearing the generic “Not So PG” attires - for that, they get major fan points from us here on The Sportster. But seriously, Tom looks like he’s having a little too much fun in the ensemble.


8 Tom & His Scooter

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Whether it be with his son or at home in the Boston area by himself, we’ve seen a number of shots featuring Brady riding his scooter - no, not a bicycle but a scooter. We all have that awkward thing we love to do behind closed doors and for Brady, it’s riding a scooter apparently. We’ve even seen photos online of Brady showing his son how to ride the damn thing, evidentially, he wants to carry on the family legacy of scooter riding. Seriously, we would pay a lot of money to watch Brady enter a Super Bowl game on a scooter through the tunnel, how insane and great would that be?

Sadly, we haven’t seen any awkward photos of Brady on a scooter in a while, though we did see him on a scooter bike in Italy in 2016, though it pales in comparison to his earlier scooter days.

7 Tom’s Combine Photo

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Even before he was drafted into the NFL, Brady looked like a generic dude and a guy you certainly wouldn’t associate with dating one of the most popular super models in the world. The awkward shirtless photo above proves that as Brady was a far cry from his current self and for that reason, he became an afterthought during the NFL Draft in 2000, getting selected 199th overall in the sixth round. Brady might be the biggest steal in draft history when you assess all of the pro sports.

He was a modest prospect but after getting selected, he would be given the keys as the starting QB as of 2001. Since then, the Pats haven’t had a losing season and have dominated the league with five Super Bowl Championships under Brady’s watch.

6 Gisele’s Past Before Brady

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Becoming the most popular super model in the world, Gisele became sought after and had an extensive dating resume before meeting Brady. Among those she dated includes Scott Barnhill, Josh Hartnett, Rico Mansur, Kelly Slater and her most covered relationship pre-Brady, Leonardo DiCaprio. At the time of their romance, the couple made all the headlines regarded at the most beautiful duo in the world, that would come to an end however following their breakup.

Looking back, it must be awkward for the couple to see such pictures from their past flings. Just imagine Leo and Brady hugging it out, though we did see Gisele and Tom’s ex-wife hug it out earlier in the article, so after all, anything is possible with the Brady family!

5 Tom’s Brother-In-Law

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When we think of the Brady family, we think of royalty and elegance. The last thing we would think of is Brady sharing the same family with former Red Sox slugger Kevin Youkilis. In an awkward twist, not only are the two related by their brothers-in-law as Kevin married Brady’s sister Julie Brady.

Seeing as both reside in the Massachusetts area, the relationship does make sense though it’s still a little awkward to assess the fact that the two are brothers. Kevin entered the family in April of 2012 and his wife Julie was pregnant with the couple’s first child shortly after. Not a bad gig for Kevin, his son’s aunt and uncle are Gisele and Tom. For what it’s worth, Kevin has stayed in the headlines thanks to his relationship with Tom recently issuing a statement on Brady’s recent Super Bowl defeat.

4 Brady The Endorsement Giant

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Such a popular figure in North America, one can assume Brady’s had his fair share of endorsement deals in the past. Like most athletes, some are memorable for all the wrong reasons and that includes his awkward relationship with UGGs. Brady rocking them furry boots was a weird sight and one he caught some heat for. He likely didn’t give a damn given the amount he was paid to work the campaigns for the company.

Among his other endorsement deals includes Stetson cologne, Aston Martin, Glaceau Smartwater and Aston Martin to name a few. His latest project sees him working with a Vegan snack company, a line of products he launched on his own back in 2016. Once the guy retires, get ready to see this list expand.

3 Brady Gone Wild

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At the Patriots Super Bowl ring party, Brady stole all the headlines for letting loose at the occasion. His dance was one of the most awkward visuals you’ll ever see, Brady was like that kid at the high school dance that just wanted to let loose and impress the chicks, though sadly this is a grown man were talking about.

Along with the awkward dance, Brady had several photos on the night looking a little glazed over, it wasn’t the first time we saw such a high profile athlete having a little too much to drink in public. We’ve seen Wayne Gretzky, Michael Jordan, LeBron James and Tiger Woods all intoxicated at one point - so if such a prestigious list of athletes are allowed, Brady certainly gets the pass as well.

2 Gisele Embarrassed By Tom’s Sweater Choice

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Be honest here, we’ve all had the moment, hell if it can happen to someone like Tom it can happen to anyone. You can recall an instance of picking out an outfit and uttering the term, “damn I look good”, only for your wife or girlfriend to see the ensemble and that feeling quickly changes to “what have I done”. Remember folks, wearing a sports jersey to a fancy restaurant is never a good idea, neither is wearing a sweater with a Pashmina under.

Spotted by the paparazzi, it was said that Gisele was furious with Tom’s wardrobe choice on the day, so much so that she was embarrassed to stand next to him. Looking at the awkward pictures of the two, we have reason to believe that the story was actually true. Not to self, never wear a thick sweater and Pashmina scarf under.

1 Gisele At The 2012 Super Bowl

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Gisele doesn’t have a squeaky clean public image; in fact, if you visit her Wikipedia page, she’s got her own section just for her past criticisms, that’s when you know. One her most memorable gaffs took place during the 2012 Super Bowl after she was being heckled by fans for Brady’s defeat in the matchup. The Giants fans got to her and Gisele was caught saying, “he can’t throw and catch the ball at the same time”, with some explicit language in between.

It caused a huge stir and one Brady likely could have done without. Needless to say, it appears as though she learned her lesson from the incident keeping things clean ever since. To her credit, she was extremely graceful in her husband’s defeat this time around, congratulating the Eagles. Though in truth, we’ll always have that awkward moment to relive.

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