The 3-year-old filly's owners also the Kentucky Cup Turf (gr. IIIT) with fellow homebred Ioya Bigtime less than an hour later at Kentucky Downs. But Leading Astray's late determination at odds of 8-1 first gave them cause to celebrate.
The Illinois-bred daughter of Belong to Me went 1 1/8 miles on firm turf in 1:49.28 under jockey Eduardo Perez, sealing the deal by a neck in a three-horse blanket finish after a game late run. It was her fifth win from six starts overall.
British-bred Miss Cato was second, a head in front of Volcat in a field of 12 sophomore fillies.
Seventh on the inside in the early going while 42-1 shot Soonerette blazed the trail, Leading Astray relaxed into an easy gallop far behind a quarter in :23.49 and a half in :48.21. She commenced her rally after three-quarters in 1:12.76, making steady progress through the field while three deep on the far turn.
Virginia Oaks (gr. IIIT) winner Volcat had taken the lead at the head of the stretch after pressing the pacesetter, and Miss Cato was breathing down her neck from third. But Leading Astray shifted four wide coming into the stretch and closed the gap of 1 1/2 lengths in the final eighth to prevail just in time.
"No real problems," jockey Mike Smith said of his trip aboard the beaten favorite, who was making her North American debut. "It was just her first time out in this country and she just got a little lost."
Out of the Prized mare Taxable Deduction, Leading Astray came into the Pucker Up after winning the second division of the $65,000 Hatoof Stakes for trainer Chris Block on Arlington Million Day Aug. 18.
"She had run through her allowance conditions and she got a little better with each start," Block remarked. "Then in the Hatoof, I told my dad this would be the test to see if we were good enough for the Pucker Up. She stepped up that day. She trained great in between the Hatoof and today. I felt really good about the race. I'm proud of her and her mama, who puts out nothing but runners."
Leading Astray is the second graded stakes winner out of her dam, who also produced two-time Stars and Stripes winner Free Fighter and the graded stakes-placed colt Suntracer. Leading Astray earned $97,650 for the Pucker Up score to boost her bankroll to $227,887. It was the second win in the race for Block, who captured the 2006 edition with Lothenbach Stable's Vacare.