The Kentucky Derby field: Will Points Ever Not Matter?

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Maybe it’s the former editor in me or that I’m just a persnickety fusspot in general, but one of my pet peeves on the Triple Crown trail is anyone saying fillies have to “face males” to run in the Kentucky Derby.
People need to stop saying that fillies have to run against males to run in the @kentuckyderby. That's only true if more than 20 enter.
— Ed DeRosa (@EJXD2) February 24, 2016
Of course that’s purposefully disingenuous. More often than not more than 20 horses will enter the Kentucky Derby and points earned in designated stakes races will be used to determine the final starting spot.
I choose those words carefully—“final starting spot”—because points serve no other purpose than to determine the last horse in. There is no prize for the most points. Ranked first means as much as ranking 20th, but it’s a big drop from 20 to 21 and an even bigger one from 24 to 25 Horses 21-24 could still draw into the field. Anyone 25th on the list or below is excluded at entry).
But if there’s no drop to 21 because only 20 (or fewer) entered then points don’t matter. Could that happen? Twitter says “NEVER AGAIN!” but history argues otherwise, and I’m on the side of history in a bet I made with Anthony Stabile—my cohost of the Horse Racing Radio Network Brisnet.com call-in show every Thursday night.
The gist of the bet is that there will come a year in which 20 or fewer horses enter the Kentucky Derby. If that year comes by 2019 (including 2019) then I win $500. In the meantime, for every entry more than 20 each year, Anthony’s pot grows $100 if that horse is excluded and $50 if they draw in off the also eligible list. If the Derby overfills through 2019 then Anthony wins whatever is in the kitty.
In Anthony’s favor is that the race has attracted at least 21 entries every year since 2010 (the year following Mine That Bird’s longshot victory). In my favor, though, is that the 2009 Derby only attracted 20 horses and that was just 4 years after Giacomo’s similar upset when people said “we’ll never have less than 20 again.”
I have no delusions that we’ll see fields in the low teens like as recently as the 1990s, but that’s not the bet. The bet is that if 20 or few enter then I win.
And one last comment on how inaccurate it is to say that fillies “have to face males.” It’s actually wrong on two levels because one, you don’t have to face males, and two, if points do come into play, then simply having faced males isn’t enough. A filly could finish sixth in the Santa Anita Derby and be in the same position as any other nominated filly who didn’t “face males.”
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