The headliner for the 2019 Kentucky Downs meet offers up some big opportunities for all the entrants. One runner in particular hopes the Turf Cup can be a springboard to becoming what his followers always thought he could be.

My Boy Jack is one of those cult hero horses that a lot of people like to root for. His huge closing kick and modest original auction price ($20,000) made him one of the darlings of the 2018 Kentucky Derby trail. Given the fact his trainer, Keith Desormeaux, had coached a deep closing Exaggerator to wins in the Santa Anita Derby, Preakness, and Haskell, in 2016, Jack looked like a prime time contender. A huge move in the Southwest Stakes at Oaklawn Park and another win in the Lexington Stakes at Keeneland meant was full of more promise than a used car salesman. But then this son of Creative Cause got mired in the mud of Churchill Downs and finished a distant fifth to eventual Triple Crown winner Justify. Jack only started once more in 2018 and that was an 8th place finish in the Belmont Derby which was run at a mile and a quarter on the Belmont Park turf.

Having cut his race horse teeth on the turf as a two year old, Jack’s versatility has given his team options. During his three year old year, he took to the dirt and opened more doors. Now running as a four-year old, Jack has spent time on both surfaces. Yet to win in 2019, the Turf Cup might be coming at just the right time as a hard charging late move at Ellis Park in the Turf Cup Preview on August 4 gave Desormeaux reasons for optimism.

“He made a serious rally late at Ellis Park to finish a close up third,” says his Cajun-born conditioner. “We were very happy with how he ran and it told us he likes running on grass again. You know its funny how he has seemed to like the grass, then he preferred dirt as a three-year old, and now I think he likes the grass better.”

The experimenting with different surfaces has given the Jack team a pretty good handle on what he likes. Disappointing runs in three starts at Churchill Downs (4th, 9th, 6th) meant it was time for the Coach to call a different play. That is where the Ellis Park experiment on the grass came in and now it’s time to take a shot in the mile and a half Calumet Turf Cup on September 7. If you are wondering about the decision to jump into the deep water of this million dollar race, it’s really a no-brainer in the eyes of his play caller.

“There’s a million reasons why we run him at Kentucky Downs,” laughs Desormeaux. “But seriously, I think I am pretty good at getting a horse ready for longer races and he is bred to love this distance. I think he is close to being back to where he was in his three-year old prime. Kentucky Downs is one of those unique tracks that levels the playing field for all the entrants. He needs to be fit going in and that’s our plan. Obviously we think he’s got a chance to show everyone what kind of race horse he really is.”

The Turf Cup will be the headliner of a blockbuster card that will feature five stakes races worth a total of $3.2 million. Defending champ Arklow is likely to be back and a full field will run for the richest purse in Kentucky Downs history. First post for September 7 is slated for 12:15.