Barack Obama’s Brackets Show Why He Was a Bad President
I have to admit: When Barack Obama first started filling out March Madness brackets, back in 2009, I thought it was pretty cool. Of course, it would turn into just another venue for him to disappoint me…
You see, in the fifteen years since he started doing it, Obama has shown himself to have one of the worst, most uninspiring strategies for filling out a bracket. More than that, his bracket strategy reveals deep character flaws that manifested themselves frequently while he was in office, and ultimately doomed his presidency.
To wit, in the fifteen men’s brackets that Obama has filled out since 2009, he has:
picked a #1 seed to win the title 12 times.
picked the #1 OVERALL seed to win the championship seven times.
picked seeds lower than 2 to make the Final Four just seven times.
picked a double-digit seed to make the Sweet 16 just eight times.
picked only nine 13-seed upsets and never picked any seed lower than 13.
What kind of psychopath fills out a bracket this way? Honestly, what is the point of filling out a bracket if you are just going to pick the #1 overall seed half the time? If you are never going to go all-in on a Cinderella, or embrace the chaos of the Tournament?
People often describe his brackets as “chalky” — Obama himself has joked about it. But plenty of people make conservative picks when filling out their brackets; that’s just a personal preference. Obama’s issue is deeper. Even when he does pick an upset, he does so only half-heartedly. He clusters around modest upsets, in the 10-, 11-, and 12-seed range, and almost never picks them to win more than one game. Even when he has a personal connection to a school, like in 2016 when he picked 13-seed Hawaii to win, he does so reluctantly: In his original, handwritten bracket, he had Cal.
Now, you might think that Obama is just being strategic. After all, higher seeds usually win — that’s why they’re seeded higher — and 1-seeds win the Tournament more often than not. So isn’t Obama just making smart picks? This is the image he cultivated as President: The guy who did the smart thing, even if it wasn’t always exciting or popular.
Except, here’s the thing: Obama’s picks are terrible! It is almost impressive how wrong he is, given how much chalk he goes with. In 14 previous tournaments, he has only twice picked the winner correctly (2009, 2017)* — that’s fewer than the times he’s had his championship pick eliminated in the first weekend (2010, 2018, 2023). He’s had more years guessing zero Final Four teams correctly (2010, 2011, 2019, 2023), than guessing multiple correctly (2012, 2015, 2021). All this EVEN THOUGH he basically never goes out on a limb.
*Am I bitter that the two times he got it right were the two times UNC won? Of course not, why would you even think that?
In other words, Obama’s bracket philosophy is not actually good at being right; it is only good for not appearing too wrong. Nobody is going to laugh at Obama when he picks all the 1-seeds to advance to the Final Four, even if none of them actually do.
And this is what I mean when I say that this bracket philosophy explains why he failed as a President. Time and again, President Obama thought he deserved credit for doing the safe and prudent thing, even when that thing did not work at all.
Instead of rushing a withdrawal from Afghanistan, Obama listened to his generals, stayed the course, and recommitted to the war. Of course, the result was an extra decade of occupation with absolutely nothing but death and devastation to show for it… but at least he made the safe choice!
Instead of responding to the 2008 financial crisis by punishing the banks or helping homeowners, Obama listened to Larry Summers and Tim Geithner, and pursued the safe, moderate path of emergency measures for banks, temporary fiscal stimulus, and generous monetary policy. Of course, the result was a glacial economic recovery that left homeowners in debt and the unemployment rate high for an extra decade… but at least he made the safe choice!
Instead of increasing health care coverage by expanding Medicare, the most popular and successful health program in the country, Obama followed the path of Mitt Romney and the Heritage Foundation and tried a free market solution that relied on an individual mandate. Of course, the result was a complicated, unpopular mess that didn’t really work and was partially struck down by the Supreme Court… but at least he made the safe choice!
I could keep going but — well, let me do one more:
Instead of picking a fun team from his hometown to make the Final Four, Obama listened to the committee and picked #1 overall seed Virginia. Of course, Loyola-Chicago made a historic Cinderella run and Virginia lost in the worst upset in Tournament history… but at least he made the safe choice!
This is a man without conviction. This is a man so scared of being wrong that he won’t do what is right. This is a political nihilist so in love with the image of himself as a leader that he doesn’t care what he is leading you to. This is a man you do not want to be in a March Madness pool with.
The thing about filling out a bracket is that nobody really expects you to be right about all of it. How could you be? Even non-presidents can’t keep up with all 68 teams. That’s not really the point. The point is to be invested and try to be right about a few, important things. That’s kind of the point of politics, too, but I’m not sure Barack Obama ever learned that…