On regret

On Thursday, May 5, I spent a few minutes looking at the horses lined up for the 2011 Kentucky Derby. (This was when Uncle Mo, the favorite, was still in the running of 22 horses total.) I sent an email saying, “I want two bets for the Derby, one for Dialed In to win and the other for Animal Kingdom.” (Within a few hours, I had also picked Nehro to come in second place either way – he had taken second in every race during his career.) So I had two bets total.

On Saturday, May 7, in the brief sunshine of late afternoon on a spectacular spring day, I placed that first bet, the one with Dialed In and Nehro for first and second. In my julep-drinking haste, I then thanked the track employee and skipped lightly away from the betting window. And I never placed that second bet – the one with Animal Kingdom and Nehro for first and second.

Less than an hour later, in the most exciting two minutes in sports, the first two horses to cross the finish line were Animal Kingdom and Nehro. The odds were so stacked against the pair finishing together that the payout for even the minimum $2 bet was several hundred dollars. Such odds were described in papers the next day as being "the perfect storm" for those who had had the foresight to bet both together. (And, of course, actually place the bet.)

And after those two horses won, my first reaction was to cheer and exclaim to our box, “somebody just won a lot of money!” It wasn’t until moments later that I realized, "oh, wait. That was my pick."

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When we had gotten dressed the morning of the Kentucky Derby, I had thought out loud: “whatever happens today, we’re going to have a good time. I honestly don’t care if my shoe breaks or it’s a torrential downpour. This is going to be a good day!"

And that was our objective: simply have a good time.

That’s what something like The Kentucky Derby is for, isn't it?

And so, after a half day of fancy summer drinks, when I was in line at the betting window, I thought: “I’m not going to worry about placing all these bets trying to secure the winning combination. I’m going to make one bet and not worry about the rest.”

Because I'd come to enjoy my day and, by mid afternoon, we'd already accomplished that. There was, I realized, little more that anything I could do at this window could contribute to the afternoon.

Even if I had won, it wasn't about the money for me.  I'm not a person who cares about being handed free cash - I genuinely wouldn't have pocketed but rather shared - in some capacity - what I would've won. (Actually, after buying a round for the box and an extra round for the newlyweds who remained huddled in the back the whole day, I likely would've taken a select few out for a great dinner or flown an even more select two of us to Charleston some weekend.) So I think the desire to win may have been rooted in the simple satisfaction of being right. And of pulling the trigger when you know you should.

And even though that realization nudged me a little on the inside, I smile as I recall the laughter that that same select two of us shared at the event - the people-watching, his ease with the cigar mirrored against my sheer awkwardness with it, the thrill of a cheering crowd, the fun of dressing up, some of the fun people we had the chance to spend some time with.

In short, I recall: I set out to have a good time, and that is exactly what we achieved. And though that second bet I never placed stayed lodged there in my ribs for a good 24 hours, I look back now and smile at the whole experience. When you have the right mindset, winning really can't add a ton to an already amazing weekend.

So, if you’re going to have regrets, only dwell on them long enough to conclude some lessons for next time.

The rules that came out of this?

1.    Always keep the big picture objectives as top priority

2.    Always. Bet. Before. Drinking. :)