Will Chicago Style Upset the Hollywood Turf Cup?

In my opinion, one of the most interesting handicapping challenges of the week is the $200,000 Hollywood Turf Cup (gr. II) on Friday at Del Mar, a 1 ½-mile turf race that pits established stars in questionable form against a handful of up-and-comers who have never won at the graded stakes level.

By far the most accomplished runners in the race are #3 Bigger Picture, #4 Can’thelpbelieving, and #5 Ashleyluvssugar. Between them, they’ve won 11 graded stakes races, and Bigger Picture has even prevailed at the Grade 1 level, defeating Can’thelpbelieving by a head in the 2017 United Nations Stakes at Monmouth Park.

But here’s the thing—all three of these stars are seven years old, and you can argue that they’ve all lost a step or two this year. Bigger Picture hasn’t won a race since January, Can’thelpbelieving last visited the winner’s circle in August 2017, and Ashleyluvssugar has been beaten seven times since his last victory in May 2017.

Now, that’s not to say that none of them can win on Friday—they’ve all fired off some solid recent runs, even Ashleyluvssugar, who was beaten just a half-length in the John Henry Turf Championship (gr. II) in September. But I don’t think they’re unstoppable by any means, and I don’t think they’ll necessarily offer much in the way of wagering value.

That’s why I’m going to take a shot with #8 Chicago Style. A five-year-old son of Kitten’s Joy, Chicago Style is lightly raced with just ten starts under his belt, but he’s already shown a clear affinity for Del Mar, winning a pair of 1 3/8-mile allowance races during the summer of 2017 before finishing second by just a neck in the 2017 renewal of the Hollywood Turf Cup.

Chicago Style was away from the races for the majority of 2018, but he returned to action in the November 2^nd Lure Stakes at Santa Anita and ran quite well in defeat. Racing over a one-mile distance that is much shorter than his best, Chicago Style dropped back to last early on, but closed well at the finish to be beaten just 1 ½ lengths against a quality field, an effort that should serve as a perfect sharpener for the Hollywood Turf Cup. With a perfect ride from the current meet-leading jockey Drayden Van Dyke, I think Chicago Style can out-finish his older rivals and post an upset.

Since Chicago Style should offer solid odds, I’ll bet him to win and key him in the exacta with Bigger Picture, Ashleyluvssugar, and #6 Marckie’s Water, a late-running winner the last two times he’s run 1 ¼ miles or farther:

$10 to win on #8 Chicago Style ($10) $3 exacta: 8 with 3,5,6 ($9) $4 exacta: 3,5,6 with 8 ($12)

Good luck!