I have followed thoroughbred horse racing for 36 years and have made just three Kentucky Derby future book bets. To snuff out a viable runner months in advance of the actual race is difficult. Actually getting the horse in the gate and navigating traffic around 19 opponents to win requires a significant amount of good luck. That is something that has never meandered in this direction.
In 1995, I bet Tejano Run. He was 70-1 in early February when the bet was placed. I liked his two-year old form when he finished third in the Breeders' Cup Juvenile behind Timber Country closing from the clouds under Jerry Bailey. A girl I knew was heading to Las Vegas and agreed to bet this horse for me. A friend of mine, who wasn't really a horse racing guy, wanted to get a bet down, too. He looked through the names of Derby candidates, and without a single past performance, picked Thunder Gulch. He liked the name.
I gave the girl $100 to bet. She was to place $50 on Tejano Run at 70-1 and $50 on Thunder Gulch at 40-1. She obliged but came back with two identical $50 tickets on Tejano Run. I'm not sure how this mistake occurred but it did. In my great wisdom, I told my friend I'd take both tickets and pay him out of my pocket if Thunder Gulch won.
Two months later, to my utter shock, Thunder Gulch, at 25-1, got the jump on the turn and held a two-length lead in mid-stretch when Tejano Run made a burst through the middle of the pack. It was too late. The most unlikely and vomit-inducing outcome happened. Thunder Gulch won and Tejano Run ran second. Not only did I not win, I was on the hook for another $2k.
Fast forward twenty years. In 2015, American Pharoah was the favorite to win the Kentucky Derby for Bob Baffert. Baffert hadn't won the Kentucky Derby since 2002 with War Emblem but been second twice since (most recently with Bodemeister in 2012). The accolades for American Pharoah were loud, and many.
In December 2014, a horse caught my attention. Firing Line had run second in his debut before winning his next start both in MSW company. The clocker reports indicated he was doing exceptional in the morning. After digging into the pedigree, I felt his 125-1 odds was worth the risk. I called up legendary horse racing writer Steve Davidowitz and asked him to make the bet for me. He did and my $100 bet would return $12,600 if he was able to win the Derby nearly five months later.
After big efforts in the G1 Los Alamitos Futurity and the G3 Bob Lewis, trainer Simon Callaghan shipped him to Sunland for the Sunland Derby. He won that $800,000 race by over 14-lengths and next stop was Churchill Downs. He ran second to American Pharoah in the 2015 Kentucky Derby at just short of 10-1 odds. For a moment in mid-stretch, he looked like the winner but American Pharoah found a little more and prevailed.
One could argue that I had bad luck to run second both times. On the other hand, it took an awful lot to go right to get those horses into the starting gate, and even more to have a legitimate chance to win.
This week, I made my third future book bet. I went with the 85-1 Brad Cox colt Zozos. This offspring of Munnings is two-for-two after a 10-length win stretching out in optional claiming company at the Fair Grounds. He beat 17 runners in his two wins and both races appear to be coming back strong. My $300 wager would return $25,800 if he wins.
The good news is Cox has indicated one of the Kentucky Derby prep races (i.e. Arkansas Derby, Louisiana Derby) would be his next race. A lot has to go right for him to make it to Churchill Downs. In my mind, if he's in the Derby starting gate with a reasonable chance to win, I consider the future book bet a success no matter the outcome.