Here We Go Again: Why Tom Brady's Donald Trump Connection Lives On

Donald Trump loves to brag about any and all celebrity support he can get, which is why you'll see him gloat anytime celebrities like Kim Kardashian and Kanye West, Roseanne Barr, Stacey Dash, Scott Baio, and Clint Eastwood (yes, even though he once yelled at an empty chair). But there's only one celeb who seems to be able to make the President googly-eyed and giddy every time his name comes up: Trump's fave Tom Brady, the love-him-or-hate-him quarterback for the New England Patriots.

Trump, who's long been buds with Patriots GM Bill Belichick and owner Robert Kraft, recently gloated about the team's Super Bowl placement on Twitter.

"Congratulations to Bob Kraft, Bill Belichick, Tom Brady and the entire New England Patriots team on a great game and season. Will be a fantastic Super Bowl," Trump tweeted.

It's worth noting that Trump did not congratulate the Los Angeles Rams.

Though things seem rosy between Brady and Trump now, they weren't always. To fully understand the relationship, we should go over some of the milestones.

Trump and Brady first met back in 2002 at the Miss America Pageant in Indiana. Brady had recently helped the Patriots win the Super Bowl against the Rams (who were then in St. Louis) and, as a young hotshot, quickly found himself climbing the rich guy social ladder. As an initiation into the club, Trump invited Brady to ogle young women and go on numerous golf trips.

Those invites left a lasting impression on Brady, who showcased his support for Trump's presidential campaign in 2015 by placing a red Make America Great Again hat in his locker. Despite telling a reporter that Trump winning the election "would be great," Brady eventually walked back his support for the controversial then-candidate after receiving backlash from fans and from his wife, Gisele Bündchen, who asked him no longer talk about politics. Of course, that didn't stop reporters from asking questions, and Brady was forced to defend himself.

"Can I just stay out of this debate? Donald is a good friend of mine," Brady said on WEEI, according to NBC Sports. "I have known him for a long time. I support all my friends... He's always been so supportive of me. For the last 15 years, since I judged a beauty pageant for him, which was one of the very first things that I did that I thought was really cool that came along with winning the Super Bowl."

Brady also said he thought Trump's decision to go from businessman to reality star to aspiring politician was "pretty remarkable."

Meanwhile, Trump didn't seem to mind one bit that people were fixated on his friendship with Brady. (After all, no one loves media attention, good and bad, more than Trump — and what's better than having his name splashed across headlines along with a Super Bowl Champion?)

As for how Trump felt that Brady wouldn't give him a flat-out public endorsement? Well, he "told him not to." Of course!

"He's got sponsors, he's got all of his different things that he has to do, and I told him not to [endorse me]," Trump told WEEI, according to the Boston Globe.

The love fest between Trump and Brady seemed to dip in 2017, however, when Brady declined a trip to visit the White House alongside the Patriots (even after Trump defended Brady over the infamous "deflategate" scandal). According to The Washington Post, Trump didn't take the news well and asked both his aides and Bob Kraft to help remedy the situation. Later, Brady claimed that the only reason he declined Trump's invite was because he had to visit his mother.

A few months later, Brady and Trump's seemingly ailing friendship once again made headlines after the star quarterback called the president's comments on NFL kneeling protests "divisive."

All of the bad blood (if there had been any) seemed to vanish by July 2018, however, when Trump made a string of odd comments about Brady and his daughter, Ivanka. The New York Times reported that Trump often "joked that he 'could have had Tom Brady' as a son-in-law." Trump reportedly also said, "Instead I got Jared Kushner."

OK, Trump and Brady have had their fair share of friend drama. It's a known fact that Trump lives for controversy — so, why does anyone care? Without having conducted a mass survey, I have a few speculative reasons.

First, both Trump and Brady are wildly out of touch with the majority of Americans. They're both excessively wealthy, married to models, and own ridiculous properties. Neither have ever likely had to worry about living paycheck-to-paycheck or wonder how they'd afford their next meal. There's something so fascinating (and infuriating) about two men who seemingly have everything thinking they know what's best for the middle- and lower-classes.

Secondly, people love villains. Would you rather watch an episode of Vanderpump Rules where everyone's happy, or would you rather watch one in which James Kennedy stirs up a shit-ton of drama? Probably the latter. That's because villains equal entertainment and a distraction from the actual horrible things (Polar Vortex, a constantly shifting stock market, and another looming shutdown) going on in the real world. It's much easier to see Trump and Brady as cartoonish bad guys than it is to actually dissect their problematic views and history.

Which leads us to the final point: Some people really do care about Brady's politics. Again it's not hard to hate the successful rich guy who (probably) supports another rich guy. It is more difficult to pinpoint some of the main reasons why. During his time in office Trump oversaw family separations, has repeated numerous racist attacks on minorities and asylum-seeking migrants, has attacked the LGBTQ+ community, demeaned women's autonomy and appearances, rallied against reproductive rights, ignored the gun violence epidemic, and blatantly abused his power in office. (And those are just a few reasons.) Supporting Trump as a friend, at this point, seems to be an endorsement of his policies and positions.

Win or lose come Feb. 3, it seems Brady's legacy is now tied to his pal Trump's.