Keying Longshot Highland Sky in the Jockey Club Gold Cup

Deauville

By Patrick Reed, courtesy America's Best Racing

One of New York’s most prestigious races is the $750,000 Grade 1 Jockey Club Gold Cup, a 1 ¼-mile event that has been won by some of the greatest horses in history. It’s also an important prep race for the Breeders’ Cup Classic, with three of the last seven Classic winners using the Jockey Club Gold Cup as their final prep. Not surprisingly, a quality field of potential Classic contenders has lined up for the 2017 renewal of the Jockey Club Gold Cup.

The expected favorite is #7 Keen Ice, winner of the Grade 2 Suburban Handicap and runner-up in the Grade 1 Whitney Stakes this summer. Keen Ice’s two biggest wins have come going 1 ¼ miles and he’s been in the best form of his career this year, making him an obvious threat to win. #5 Rally Cry, runner-up in the Grade 1 Woodward Stakes last time out, and the speedy #1 Diversify, easy winner of the Evan Shipman Stakes at Saratoga with an eye-catching 108 Beyer Speed Figure, are others that could attract wagering support, though I’m more intrigued by #4 Pavel, an up-and-coming 3-year-old that won the Grade 3 Smarty Jones Stakes in impressive fashion last month. With just three starts on his belt, Pavel still has lots of room for improvement and could be poised for a solid run in his first start against older horses.

But despite the presence of the above-mentioned horses, I’m tempted to take a shot with #2 Highland Sky at long odds. He’ll be racing on dirt for the first time, but his record on turf suggests that he could be a threat. Trained by Barclay Tagg, Highland Sky finished second in the Grade 1 Belmont Derby going 1 ¼ miles last summer, a race in which he produced a tremendous finish to fall just a neck short of catching Deauville (an accomplished runner in Europe) while finishing ahead of the future three-time Grade 1 winner Beach Patrol.

Highland Sky didn’t run again in 2016 and is just 1-for-5 this year while competing in allowance races, but on several occasions he’s found himself in slow-paced races that made it almost impossible for him to rally from behind and win. The switch to dirt could bring about different results, as the pace should be quicker and Highland Sky has reportedly trained well on dirt in recent weeks, giving hope that he can be positioned closer to the pace and not fall quite so far behind early on.

So let’s take a shot with Highland Sky at a big price and see if we can’t make a nice score if he wins or hits the board. Here’s how I would play the race:

Wagering Strategy on a $10 Budget

$3 to win on #2 Highland Sky ($3)
$4 to place on #2 Highland Sky ($4)
$0.50 trifecta: 4,7 with 1,4,5,7 with 2 ($3)

Wagering Strategy on a $20 Budget

$5 to win on #2 Highland Sky ($5)
$3 exacta: 4,7 with 2 ($6)
$1.50 trifecta: 4,7 with 1,4,5,7 with 2 ($9)

Good luck, and enjoy the race!