If You’re Looking for a Kentucky Derby Sleeper, This Is Your Horse!

If you like deep closers, dark horses, longshots or Cinderellas (who doesn’t?), then I have a rooting interest for you in this year’s Run for the Roses. His name is My Boy Jack and he’s currently 18-1 on the the US Racing future odds board.

The dark bay colt was purchased for $20,000 at the 2016 Keeneland September Yearling sale.  Yet, he has already accumulated over half a million dollars ($645,145) in earnings. He is owned in a partnership that consists of Don’t Tell My Wife Stables (love the name) and Sol Kumin’s Monomoy Stables. However, less than a week ago, West Point Thoroughbreds purchased a minority interest in the multi-graded stakes winner, who is trained by Keith Desormeaux and ridden by his brother Kent.


“I’ve always liked this horse and admire his versatility [ability to run well on different surfaces]. We liked him since the Breeders’ Cup Turf race last year,” said West Point President and CEO Terry Finley.

My Boy Jack has won on both turf and dirt. He has won on dry, fast tracks and on a sloppy, sealed track.

“He always fires. He’s a fighter. To use a hockey analogy, he’s willing to drop the gloves if necessary,” said Finley.

How did West Point Thoroughbreds, which owned a minority share in last year’s Kentucky Derby winner Always Dreaming, get involved in partnership deal? Terry Finley explains: “I got a call from my agent asking if we were interested. We had been looking for an opportunity [to own a Kentucky Derby horse], but nothing was there. Always Dreaming gave us a great ride last year. So, we jumped at it.”

West Point Thoroughbreds has 30 percent ownership in My Boy Jack.

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My Boy Jack will be one of the most experienced horses in this year’s Kentucky Derby field with 10 career starts. If you read my previous article “Who’s Your ‘Daisy’ in the 2018 Kentucky Derby?” you know that I think My Boy Jack has the necessary closing speed to be a Derby winner.

My evaluation of his closing speed from his third-place finish in the Louisiana Derby was followed up with a more impressive effort in the 2018 Lexington Stakes (below).

And if this year’s Kentucky Derby run on a sloppy track, My Boy Jack shoots up my contender ranking list. He won impressively in the sloppy Southwest Stakes at Oaklawn Park (shown below). Note that My Boy Jack’s winning time of 1:46 flat was just 0.22 seconds off what American Pharoah recorded in 2015 in the Rebel Stakes — same 1 1/16-mile distance, same Oaklawn Park track, same sloppy track conditions.

My Boy Jack’s jockey Kent Desormeaux worked wonders with closer Exaggerator in sloppy, off track conditions a few years ago. Who were the last two deep closers to win the Kentucky? Mine That Bird (2009) and Orb (2013). Both won on a sloppy, sealed track. If you have become a My Boy Jack fan by now, pray for rain.


Overall, I like My Boy Jack’s pedigree. Admittedly, it’s not my favorite of this year’s projected Derby entries, but it’s good enough to get a thumbs-up from me, especially since the colt was purchased for a bargain price of $20K.

Something I love: My Boy Jack has Secretariat on both his sire’s and dam’s side. The last five Kentucky Derby winners all had Secretariat on at least one side of their pedigree, which I noted was an unusual new trend last year in a US Racing Derby profile on Malagacy. He also has Northern Dancer on his sire’s side and Seattle Slew on his dam’s side.

My Boy Jack’s sire was Creative Cause, who won the Grade 1 Norfolk Stakes, Grade 2 San Felipe Stakes and finished second in the 2012 Santa Anita Derby behind eventual Kentucky Derby winner I’ll Have Another. He went on to finish fifth in the Kentucky Derby and third in the Preakness Stakes. Creative Cause’s sire (My Boy Jack’s grandsire) was Giant’s Causeway, who won 9 of 13 races over his career (five Group 1 races in the UK) and finished second in the 2000 Breeders’ Cup Classic in his first and only start on dirt.

My Boy Jack’s dam, Gold N Shaft, never raced.  However, her sire Mineshaft was victorious in 10 out of 18 starts, including three Grade 1 races in 2003 (Suburban Handicap, Woodward Stakes and Jockey Club Gold Cup).

The Bottom Line

My Boy Jack’s deep closing style and late speed should bode well in this year’s Kentucky Derby, since it looks to have plenty of early speed. Unfortunately, this year’s Derby crop is loaded with talent and My Boy Jack’s overall speed figures pale in comparison to other contenders.

For this reason, on a dry, fast track surface, he probably won’t be my race favorite, but I am not sure that I have one yet. However, My Boy Jack does have the potential to hit the board (finish third or better). So, I recommend including him in your Derby exotic bets.

And if it rains hard this Derby day, then I like his chances even more and may move him up to my race favorite.

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