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An Oral History of Betting the Kentucky Derby and Maximum Security


Credit: Horseracingnation.com

I don’t bet a lot of horse racing in large part because I admittedly don’t know how to handicap it. I grew up by a race track, of which I frequented as a teenager, made plenty of $2 show bets with the hopes of turning that into some extra beer money, but my skill level peaked at, “Dude, it’s a Baffert horse, it’s gotta be good!”

Nowadays, when I do bet the ponies, it’s per someone else’s recommendation — and by someone, I mean a trusted colleague who displays knowledge on the subject and will put me in a far better position to win compared to that of my “Baffert angle.” On Friday, we had a Kentucky Derby segment on the BettorIQ Podcast with Micah Joe. Micah doesn’t handicap horse racing full-time but has experience on how to approach Triple Crown races as well multiple contacts. Micah’s pick to win the Kentucky Derby was Maximum Security (listen here at 15:58). After the segment, Micah and I talked off air about how to bet Maximum Security — his odds at that time were +750. Micah felt those odds may be better come race day and with matchups (Horse A vs. Horse B) not yet posted, I decided to hold off.

Saturday morning, as I was line shopping for MLB, I noticed the matchups were finally posted and I sprung into action. A lot of offscreen sportsbooks copy each other but I happen to get lucky with one that had significantly better odds on Maximum Security. Behold…

I’ve been betting for well over a decade and getting “the best of the number” never gets old. Four matchup bets, all on Maximum Security, and all great prices compared to the prevailing market. I then went about my day, which involved trekking 45 minutes to an all day, rain-soaked 12u travel baseball tournament. Not my idea of fun — and my kid had better get some sort of scholarship to recoup the ridiculous cost — but with the advent of cellular technology, I could at least track games and make some wagers on the fly.

As the day wore on, post time for the Derby neared. I knew heading in that tying up all of my bets on one horse with such a large field was risky. I’ve had years where the horse I keyed in on tanked. Others where I split out. And a few where I managed to turn a small profit. I can honestly say that I’ve never “crushed” the Derby which makes perfect sense considering I don’t handicap horse racing and don’t associate with anyone who does it full-time. I also don’t generally mess around when it comes to my bankroll. In the immortal words of Joey Knish, “I’m not playing for the thrill of fucking victory here…” But I’ve always had a soft spot for the Kentucky Derby and chucking out a few bets on the “fastest two minutes in sports” remains my one guilty betting pleasure.

Around 10 minutes before the race, I received an unsolicited text from a close friend who has next to no betting experience. The text read as followed…

“I’ve decided Maximum Security sucks.”

I have yet to ask him what prompted such a brash statement but after receiving it, a rush of increased confidence warmed over me. Had it been a Week 15 NFL side, I probably would have bet a little more on the other side — the old “handicap the handicapper!” — but again, this is the Kentucky Derby where virtually everyone is tossing darts at a dart board blindfolded. I at least had a recommendation coming from a valued source, some damn good numbers, and a random text message from a betting greenhorn saying my chosen horse “sucks.” It wasn’t beating the closing line of a college basketball total by eight points but I felt like I had a fighting chance.

Wondering why my kid decided to take a center cut, first pitch fastball, I lost track of time only to have my wife approach me with news that Maximum Security had emerged victorious. Holy shit! I rarely if ever talk about my business with others, especially “baseball dads.” The main reason is the amount of questions they ask followed by the obligatory, “Hey, man, who do you like on Monday Night Football?” But in this instance, I pretty much let the entire ball park know that I was on Maximum Security — a total “amateur hour” move given what was about to occur. I checked my account a few minutes later and was miffed my winnings had yet to be credited. That is when the gentleman next to me said that the race was under review. I’m pretty balanced when it comes to betting optimism and pessimism. You do this full-time and you’ll undoubtedly endure more than a few favorable and unfavorable bounces. But the minute I heard the results were still pending, I pretty much knew I was screwed. Sure enough, Maximum Security was in fact disqualified and long shot Country House was named the winner. Due to my inexperience of betting horse racing, I for a brief second wondered whether or not my bets would be graded as a “push” but quickly realized that was ridiculously illogical on multiple levels. All four bets where losers and like a lot of bettors, there was nothing we could do. Adding insult to injury, a number of “rec bettor” sportsbooks decided to jump on the publicity train and offer refunds to those “bad beat” bettors.

What’s funny about this experience is that I still haven’t seen the race. Similar to watching a basketball player blowout his knee on instant replay, I simply can’t stomach it. Despite the public outcry, I took some solace in the fact that someone I respect and that follows horse racing closely felt that the DQ was warranted. The hit to my bankroll was minimal in the grand scheme of things — thanks, Joey! But the whole ordeal still stung, enough that I probably won’t bet the Preakness or Belmont. Of course, if Micah feels strongly about another horse and I get any more “sucks” text messages, I may change my tune.

Andrew Lange

With significant market influence, Andrew Lange has produced a decade-long 58% winning rate on over 750 selections in college basketball. Using a low volume, high return approach, Lange's results in the NFL have been equally impressive with a 61% mark and over +49 units of profit on a 1, 1.5, and 2-unit scale since 2012.