My Boy Jack Enters Pantheon of Kentucky Derby Underlays

by SCOTT SHAPIRO

Justify and Mendelssohn may have had the most hype leading into the 2018 Kentucky Derby Presented by Woodford Reserve, but those watching the wagering on America’s most famous horse race could not stop talking about the money bet on My Boy Jack.

Yes, there were some things to like about the Stonestreet Lexington Stakes winner— wins in his most recent start and in the slop among them—but no one could make the case for his 6.7-to-1 win odds, good for second choice in the field of 20. I.e. win bettors gave My Boy Jack a better chance of wearing the roses than the aforementioned Mendelssohn, champion Good Magic, or Grade 1 winner Audible.

Yes, in the context of the weather on Saturday—the wettest Kentucky Derby day on record in Louisville—it was not surprising that the Keith Desormeaux trainee took a good deal of money based on his impressive score in the Southwest Stakes in the slop at Oaklawn Park. However, the money came in on Friday when it was dry and even with rain in the forecast for Saturday a wet track was no certainty.

Few horseplayers support the Desormeaux brothers more than I do, and the 30-1 morning line was probably higher than the son of Creative Cause should have been given his resume, but his final odds as second choice against a good field left many scratching their heads.

The crazy action on My Boy Jack made me wonder whether he was the biggest underlay this century in the Kentucky Derby. Here are a few other examples of horses that took much more money than expected over the past 18 renditions (this period also fits because 2001 was the first year there were no coupled entries):

Patch (2017)- The Calumet Farm colt entered last year’s Derby with just a maiden win and a second place effort in the Grade 2 Louisiana Derby. The son of Union Rags was listed at 30-1 on odds maker Mike Battaglia’s morning line, but was bet down to 14 to 1. Much of this can be explained though by the media attention he received for having just one eye. He finished fourteenth, but rebounded well with a third-place finish in the Belmont Stakes five weeks later.

Candy Boy (2014)– The John Sadler trainee was listed at 20-1 in the 2014 Derby after notching 2 wins in 7 victories before his voyage to Louisville. His inability to compete with eventual winner California Chrome in the Santa Anita Derby did not scare bettors away from him though in Louisville where he was set off at 9.4 to 1. The son of Candy Ride encountered serious trouble on the first turn and never recovered.

Pants On Fire (2011)– The son of Jump Start entered the 2011 “Run for the Roses” off a neck victory in the Grade 2 Louisiana Derby, but his only win prior to that came in a maiden race at Delaware Park in the slop. He was made a 20-1 long shot in the program, but ended up going off as the 8 to 1 second choice behind Dialed In. He finished ninth for trainer Kelly Breen. Much of the wagering support can likely be pointed to the fact that female rider Rosie Napravnik was getting the leg up. Napravnik was the first woman to ride in the Kentucky Derby since Rosemary Homeister in 2003.

Saarland (2002)– Shug McGaughey brought this Kentucky bred into the 2002 Derby off of a fourth place finish in the Wood Memorial. The son of Unbridled had a neck win in the Remsen on his resume and had trouble in the Wood, but was over bet from his 15-1 morning line. He went off the co-second choice at 6.9 to 1, but never factored in the outcome, in large part due to a race dominated by front runners. He later posted some strong underneath efforts in some of New York’s biggest stakes races, but never got his picture taken in a Grade 1 or Grade 2.

After an in-depth investigation of the Kentucky Derby wagering since 2001 I have to declare My Boy Jack the biggest underlay this century. He was just one of five horses in this strong group that had not put forth a triple digit BRIS speed rating prior to the first leg of the Triple Crown and his running style almost guaranteed a less than perfect trip.

This conclusion by no means should be seen as a critique on those that came up with My Boy Jack after handicapping the race or of my personal opinion of the bargain basement $20,000 Keeneland September 2016 purchase. In fact I have a great deal of admiration for the horse and his turn of foot. Making him the second choice in this group is just hard to understand.

One will never know why this colt took so much money, but without question he was way over bet. Some point to the popularity of the name Jack as being the reason for the excessive amount of money on a horse that on paper should have been sixth or seventh choice at best, but that is an awful lot of small win bets given the size of the Kentucky Derby win pool. To me that might explain him being 10 or 11 to 1, but not the second choice when the gates sounded.

Since 2001, Kentucky Derby starters in 20-horse fields who went off at odds of less than 7-to-1:

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