My first experience with an NCAA Men's Basketball Tournament Pool was in 1988, when a buddy named Frank White who was in law school with Bill Hale, Ronnie Harrison, Todd Davidson and some other friends of ours put together a $5.00 per entry pool where participants filled out a bracket before the tournament began and were awarded points for each correct pick in each round. The participant with the most points after the National Championship Game won all the prize money. There were twenty of us who entered that first year and my Dad won the $100.00 first place prize. We did it again the next year and Dad won again - this is his claim to fame besides being the Yo-Yo Champ when he was a kid and the son of the one and only Checker Champ, Carl Estes Oldham.

Frank graduated from law school in 1989 and I decided to keep his pool going. While twenty participants was fine, I had bigger ideas and thought it would be even more fun if we could generate a bigger pot. The first year I was running the pool, I talked it up with family and friends and was able to muster a total of 65 participants, with my good buddy Mike Cavalier winning it after UNLV beat Georgia Tech in the Final Four and broke my Mom's heart (as is sometimes the case, that particular Final Four match-up was the one that determined the ultimate winner). Almost all of the participants that year were law students and family members and I hand-scored the brackets and passed-out the results in person after each week. It was great fun for all involved - not to mention a nice little payday for the Ragin' Cajun - and I decided I would try to make the pool as big as I could get it the following year.

Since I had done a good bit of computer programming over the years and saw the power that those machines had to make one's life easier, I had begun writing a program in the BASIC language in 1990 that could handle the scoring for that year's pool rather than Lynn and I having to do it by hand (it took a minute or two per sheet after each round to compare each participant's bracket to the results and total the points and when one multiplies that times 65, it took several hours of administrative time to run the pool). In true LCOPC fashion, I began working on the program about a week before the tournament commenced and once the games began and it was apparent the programming was not going to be 100% complete, I shelved it until the next year, resolving to get everything working before the first tip-off of the following year's tournament.

The initial thought process was that I needed to have something to make the scoring easier once all of the data from the hand-filled sheets was entered and with the limits of technology in those days, I had no practical way for participants to enter their own data into the program. Because it had been so time-consuming to hand-score the 65 entries from the year before, I told myself that I was going to finish the computer program before the next year. Between golfing, studying case law and enjoying married life with my one and only, however, I never could find the time to get back to the computer and before I knew it, the Madness was just around the corner and I would once again be scrambling to finish the program. There were 177 participants in the 1991 rendition of the pool due in no small part to my arm-twisting in the UGA Law Library and the $884.00 winner-take-all first prize money got everyone excited. This meant, of course, that the people would be demanding their results and I had to deliver on time. While I was much further along with the programming than the prior year, I still was not able to get everything working the way it needed to before the games started coming fast and furious and I had no choice but to go back to the hand-scoring approach from the prior year.

I graduated from law school in 1991 and a number of my classmates asked me if I still planned on running the pool. I said that I would as long as there was enough interest in it and so began a journey that has lasted more than 30 years and led to a number of operational improvements that have resulted in what participants see today. I have spent hundreds of hours and thousands of dollars to get to this point and participants seem to look as forward to this thing every year as I do. Following is a bit of a trip down memory lane.

For those young whipper-snappers among us who have never lived in a world that did not include the Internet, life was much different back when I got out of law school, just like it was much different for the generations that preceded ours. That first year out in the real world, I ran the pool through the U.S. Mail back in the days when the mail was reliable. The entry fee was $6.00, which covered the $5.00 entry fee and the cost of three $.33 stamps so Lynn and I could mail out the results. It worked just fine, although there was a good bit of effort involved in scoring the entries, tabulating the results and getting everything out in the mail. I started my legal career at Andersen, Davidson & Tate, P.C. in Lawrenceville, Georgia and continued to hand-score the results until I left there in 1994 with the pool enjoying a consistent level of participation.

As technology advanced, I eventually was able to send reminders and receive brackets using WinFax, a software program that allowed me to reach a larger number of potential participants through the magic of facsimile transmissions. There was no such thing as the Internet or email at that point in time and I was still receiving a number of entries through the mail. I began working at Cushing, Morris, Armbruster & Jones in 1994 and at some time before I left there in 1998 to start my own firm, I had finally finished the computer program that would allow me to score all of the entries automatically. By that time, the pool had a faithful following and continued to grow organically through referrals from participants and their family members.

By the time I started Larry C. Oldham, P.C. in 1998, I had a working computer program and was actively recruiting participants in the pool, calling old law school classmates and friends each year and arm-twisting entries over the telephone. I also was receiving numerous calls every year asking if I was still going to be running the pool and just catching-up in general. I loved this aspect of the process as it allowed me to find-out what was up with old friends, but as you can imagine, it took me multiple hours each March to talk to everyone - a five minute conversation for each of them but five hundred minutes worth of conversations for me. I am not complaining, mind you, but it was a ton of time that I spent every year from when the official bracket was announced on Sunday to when the First Round started on Thursday and that was just the tip of the iceberg.

With the computer program now doing what it was supposed to do in calculating results, the next problem I needed to solve was reducing the time for data entry. Dad and I would get together for years every Thursday and Friday evening of the Tourney - not to mention as necessary on Saturday and/or Sunday as well - in order to enter into the database all of the entries we received. Lynn would help as well, and there were many times that one or more of the three of us nodded off working our way through the Final Four. I program used the MSDOS operating system and the way to enter each participant's bracket at that time was by picking between Team 1 and Team 2 for all 63 games of the Tournament, which took roughly 3 minutes per sheet assuming nobody made any mistakes. Those were some great times that led to a lot of laughs over the years as Dad and I evaluated each one of the brackets as we were entering the data. He was "read man" and I was "computer data entry man" and although the games were playing on the TV in the background as we sat in the living room over at Mom and Dad's house entering picks, we rarely had time to watch any of them because it took some concentration to get things right and I knew that the people in the pool would be clamoring for the results shortly after the weekend's games were over and I always have aimed to please.

As the years went by and technology got better, it became clear that the real bottleneck that was causing the time commitment to go "off the charts" was the required data entry by Dad and I. While it was fun, the more the pool grew in size, the more that data entry was getting to be way too time-consuming for a couple of working stiffs and I resolved to come-up with a better way to address that issue so I could get us out of that business. What saved the day was me figuring out how to save the MSDOS program as an executable file that I could compile and allow participants to download so they could enter their own picks themselves and email them back to me. While that method helped a good bit, it was not fool proof and had its own set of challenges, including the data entry program being rejected by some software security systems because it appeared to be a computer virus.

Not all participants were able to figure out the data entry side of the equation and I had no iron-clad ability to insure data integrity, so I often spent hours fixing glitches caused by the failure of the software to error check or the human error that was part of the data entry using that original program. As our first two sons, Matt and Rob, got old enough to help me with data entry, the pool became even more of an Oldham Family Affair that now involved three generations. Their younger brother, Drew, got hooked on March Madness and the pool at eight years old after his beloved Georgia Bulldogs made the Big Dance in 2011 and once his brothers headed off to college at UGA, he took their place as someone I could count on to help me with the occasional manual entry of hand-filled tournament brackets from those who were still struggling with the electronic bracket.

More and more people began to participate in the pool and as I improved the software, it became possible to expand it while actually lessening the workload a little. While our boys have given me plenty of grief about WebDecoder over the years, the true break-through came in 2011 when I was able to have one of our first web developers, Chris Barnes, convert my MSDOS program and the logic embodied in it to something that I could make available on the worldwide web. Chris did a great job with the first version of the web-based program that everyone uses today and as the years went by, I had assistance from Paul Carrahan, David Frederick and the man who became our lead developer at WebDecoder, Drew Martin, to perfect the programming logic so that the cloud-based system worked even better than the one that used to run only on desktop machines.

My partner at WebDecoder, Donnie Causey, gave the web-based interface its first face-lift around 2016 and I learned enough about HTML and the CakePHP framework over the years to make everything look and feel the way I wanted to for the most part. Matt and Rob convinced me to add electronic payment methods several years back and doing so has made it easier to collect entry fees and streamline the payment process somewhat, although the true breakthrough would be tying the payment process to the individual brackets entered and I am not sure if I will ever be able to make that a reality. I have continued to revise the programming on the administrative side as time has gone by and Drew has been gracious enough to help me with some of the fine-tuning, even though he hates the way the program has been "Frankensteined" together by all of those involved in its creation over the years. I thank goodness that I have been able to convince him from time to time to address something that could make my life easier on the administrative side and my ultimate goal is to leave the application in the type of shape that will allow my sons or maybe even my grandchildren to carry on with this tradition years after I am gone and then to pass it on to their own children. I know that sounds a bit like George Costanza and the Frogger Machine, but I would love nothing more than knowing that Livi Oldham is one day carrying on her PeePop's tradition as she becomes the fourth generation of Oldhams to be involved in the pool.

What I realized in putting this history write-up together and looking over some of the past weekly write-ups I have prepared - including the 2025 reminder email that I sent out last week - is that I have been talking about making programming modifications to this pool ad nauseam and it is time for me to recognize that nobody really cares. As my brother Steve told me long ago, all participants want to be able to do is enter a bracket, enjoy the games and have a chance to win some money. I will admit that the more that I have looked under the hood of the system, the more thankful I am that the various improvers and I have been able to cobble it together to work as well as it does. I have vowed every year to learn more about the HTML, PHP and JavaScript that makes this system run so that I can improve upon it and all I can say is that I have come-up short to date. Every year as we come out of winter and into March, I just know that this is going to be the year that I break the log-jam and make substantial progress towards where I want things to be.

I talked to Drew earlier this month about addressing a few irritations that have persisted for me but I felt bad about even asking him to help and I knew he was only being nice when he said he could give me about three hours of his much-demanded time, so I told him I would only have him mess with it after I looked at it myself. After doing so in detail, I finally understood that the reason he has refused to have anything further to do with it for as long as he has is because it truly is a cobbled together mishmash, with each subsequent improver doing what he could to make the thing work better than it did before but with there being some fundamentally flawed software development decisions made from the outset that have gotten it to the point where it is but will not allow it to go any further without a substantial overhaul.

As it happens, my Mom was telling me all about the wonders of Grok 3 at a recent one of my weekly Thursday morning breakfasts with her and Dad and Donnie also has been using AI to assist him with some programming needs on the WebDecoder front for quite a while. After being told by Mom that I needed to either get with the program as it pertains to AI or get left in the dust, I figured that I would try my hand at a little ChatGPT assistance with the Madness application prior to this year's tournament. My occasional partner-in-crime, Stuart Teague, also tells me that he is using the AI interface that Westlaw provides and he claims it has revolutionized his practice. Naturally, I asked myself if binary-based brains can do that for the law, then why not for a little old basketball pool?

I set-out to see what I could accomplish myself and ended up carrying on a typewritten conversation with a cloud-based being as I worked to make some seemingly simple improvements to some of the code being used in the application. That overall experience confirmed something that I always have heard and known when it comes to computer programming, which is the concept of "garbage in, garbage out". It became painfully clear to me that if Grok 3 or some of his brethren do not understand the entire picture, it is difficult even for them to put Humpty Dumpty back together again. This most recent experience has caused me to take a step back and appreciate what I have, with me now leaning towards leaving well-enough alone and just dealing with the limitations and workarounds I contend with every year, which are not that big of a deal in the grand scheme of things. After all, there are bigger fish to fry in the world in which we all live and a man has to pick his battles, which is something one of my favorite people in the whole world once told me when I was telling her she needed to make sure the staples were straight when she was putting together documents to go out the door back in the early 2000s – good ol' RGV, Lynn and I continue to love her dearly.

The bottom line is that after years of considering the possibilities of what I might be able to do with the current application, I have come to the conclusion that it is as good as it gets. I can either live with the limitations or go back to the drawing board, but there are two things that I will never do: (i) dumb this thing down and run it on a CBS March Madness bracket, as has been suggested by some acorns that did not fall far from the tree; or (ii) continue to talk about the improvements I am going to make to the program. It either will improve or it will stay the same, but no one is going to hear one word about it from me until it is in a final form acceptable to me. The thing about the chase for the Holy Grail, after all, is not necessarily about finding it, but about the journey involved in trying to find it.

I thought it would be fun to interview all of the Oldham Family members who have given their time and efforts to the cause over the years - and it truly was - and I put together a video in 2024 which was my 35th year of running the pool that I hope everyone who decides to watch it enjoys. Family and friends are what have kept this thing going for all these years and they are the reason I look forward to every rendition of March Madness - I trust that most of you feel the same way. I welcome other videos, pictures and posts from friends of the pool and I will make them available if I receive them.