March Madness – Artificial Intelligence vs Author’s Intuition
Man versus Machine.
In 1997, an IBM computer defeated World Chess Champion, Garry Kasparov, 3.5 to 2.5, in a best-of-six tournament.

Credit via The Today Show
In a game of Jeopardy! back in 20ll, IBM’s Watson AI took on former champions, Ken Jennings and Brad Rutter, and beat them on National Television.
In 2016, playing the game of Go, Google’s AlphaGo defeated World Champion Lee Sedol, demonstrating AI’s ability in complex strategic games.
How did I know all that?
Well, by asking Artificial Intelligence (AI).
And now, in 2025, bracket fillers just can’t wait to hear what ChatGPT, DeepSeek, Gemini, and other AI products have to say about March Madness and their hoop predictions.
“Artificial” Intelligence. I say bring it in for the “real” thing.
With March Madness starting on Thursday, I am going to show you how to fill out those brackets the old-fashioned way. No chips or servers required.
Unless you’re at Hooters watching the First Four games.
• Let’s start with the First Four games. AI did a great job predicting which teams would make the field of 68 by using complex algorithms, predictive metrics, quad wins, and numerous other variables. But apparently, it missed two critical factors when it left North Carolina off the list. Ratings and revenue.
• In the first round, take a sec, and then fill out your brackets with chalk. Historically speaking, the average amount of upsets that occur in the first round is just 4 out of 32 games. You’re not going pick the correct 5 vs 12 game, so just go with the favorites.
• And when I say, take a sec, I mean take a SEC. The SEC has 14 teams in the tournament. Auburn and Florida are a one-seed, Tennessee and Alabama are a two-seed, and Kentucky’s a three-seed. Take them all in the first round. Georgia (9) over Gonzaga (8), Oklahoma (9) over UConn (8), Arkansas (10) over Kansas (7), Vanderbilt (10) over St. Mary’s (7) – Take them all.
• I asked AI to give me the best starting five in the SEC and it answered, “Gensler, Peirce, Crenshaw, Uyeda, and Roisman.” But apparently, those are the five board members of the Securities and Exchange Commission.
• I also asked AI to give me the best 5 vs 12 upset, and it likes Yale over Texas A&M. Yale and AI are both awfully good at numbers and percentages, but Ivy League over SEC – probability not.
• AI also liked UC San Diego (12) to upset Michigan (5). Although, it may have thought that I was asking about Engineering Programs and not hoops.
• The second round stays relatively chalky as well. But I do like Clemson (5) to take out Purdue (4), and BYU (6) over Wisconsin (3).
• Not surprisingly, AI really likes Texas “Tech.”

Credit via AP News
• The Sweet 16 teams that advance will be Auburn (1), Duke (1), Florida (1), and Houston (1), along with Michigan State (2), Alabama (2), St. John’s (2), and Tennessee (2).
• AI didn’t predict the Sweet 16 much different, apart from having Kentucky (3) advancing instead of the Volunteers.
• I would like to think that I’m as smart as AI. The reality is, between writing, editing, and hoops predictions, it’s taking my starting job faster than an incoming transfer.
• Although, when I asked AI what Drake’s record was, instead of replying 30-3, it started playing $ome $exy $ongs 4 U.
• In the Elite 8, look for Auburn, Florida, Houston, and Alabama to move on. Auburn makes people nervous losing 3 of their last 4, but John Broome and company are number one for a reason. Florida is playing better than anyone right now. Houston’s been solid all season. And while I love Duke’s four superstars in Isiah Evans, Kon Knueppel, K’haman Maluach, and Cooper Flagg – they are all freshmen.
• AI disagrees and has Michigan State over Auburn, Florida over St. John’s, Houston over Kentucky, and Duke over Alabama. Although I think someone loaded NIL money as a data point.
• Great. I give you three one-seeds and a two, and AI gives you three one-seeds and a two, but it’s the genius. No offense AI, but what’s the point of telling me that the odds of a perfect bracket are 1 in 9.2 quintillion – if you can’t make one.
• In the Final Four, give me Florida over Auburn, and Alabama over Houston. The Gators have already handled the Tigers once this season, and Alabama beat Houston earlier in the season. Doesn’t mean much, but no one is going to be intimidated. AI had Duke and Florida advancing to the Finals.

Credit via SFGate
• Speaking of intimidating, those self-driving cars freak me out. I just want to channel my mother and yell, “Two hands on the wheel!!!”
• Finally, take the Florida Gators to win it all. The team won 30 games, haven’t lost in months, they have a bunch of pros, a ton of transfers, veteran leadership, and they play in the SEC.

Credit via Slam Magazine
• AI likes Duke to win it all and I get it. Artificial intelligence makes business decisions. They just better hope that Cooper Flagg doesn’t.
Look, you can follow technology on the Road to the Final Four in your self-driving AI vehicle that goes 32-mph in a 35-mph zone, stuck behind a parked truck, braking for every squirrel that flinches, listening to Drake…
Or you can ride with me.
Credits via destinationdayton, apnews, sfgate, slammagazine, thetodayshow