Artificial intelligence is a fact of everyday life and it is everywhere. Bracketology has grown more and more sophisticated over the years and there are a number of experts who will provide more information than any human being could possibly digest. When picking your bracket, keep in mind that although there is a good bit of money to win, picking a bracket is all about your own personal efforts and there is no place for electronic brains to make the choices that you otherwise should be making yourself. As with many other circumstances in life, something that separates human from machine is morality and principles and while some of us may be tempted to get some help from the cloud, doing so in any substantial manner really defeats the spirit and intent of the Pool.

Interestingly enough, my sister Theresa, who is a perennial contender for the $1.00 last place prize but also one of the best sports I know and a person whose morals and ethics are above reproach, left me a message on Wednesday evening that she wanted to talk to me about using AI in picking a bracket. Thinking that this could lead to some interesting back-and-forth, I decided to record the conversation for posterity's sake (I told her about it after the fact and got her permission to share it with everyone in the Pool for what it is worth). It turned out to be an thought-provoking conversation and I had shorter versions of same with a couple of other participants that I have known for years and who are also are unstanding citizens. I know that people use AI in some form or fashion in online gambling and because I had not touched on it thus far, it makes sense to address it in the context of this Pool.

I have included my initial conversation with Sis for the information of those who care to listen to it and I plan to follow-up with her after the First Week's games to evaluate how her new friends handled things for her and to see what else we might learn from the experience. We both agreed that it makes sense to record that conversation as well and I will add it to this webpage when we get a chance to do the debrief.

The time I spent last night with Sis led to a discussion this morning with Mom and Dad regarding artificial intelligence and its place in the Pool. After talking extensively about Grok3, I could not resist giving it a try myself, and here is what ensued (this unedited version may be a little long, but it was definitely enlightening):

So I finally had my debrief call with Sis regarding her AI picks, with both Deep Seek and Grok 3 turning in dismal performances. We talked through it and have some theories about what may have gone wrong and why AI may not be a good way to go, especially if you have performed poorly in the Oldham Pool in the past:

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