Joseph V. Shields Jr.'s Puzzlement squeezed through a hole on the rail with jockey Jorge Chavez and went on to post a surprise victory over bridesmaid of the year Volponi in the $300,000 Saratoga Breeders' Cup Handicap (gr. II).
Trained by H. Allen Jerkens, no stranger to upset wins at The Spa over the years, the 4-year-old son of Pine Bluff won by 3 1/4 lengths. Volponi, ridden for the first time by Jerry Bailey, was 1 3/4 lengths ahead of Iron Deputy. The final time for the 1 1/4-mile test on a fast track was 2:03 2/5.
Puzzlement, who was second in last year's Peter Pan (gr. II) at Belmont, wa coming off a fourth-place finish in the Whitney (gr. I) on Aug. 2. The bay colt closed nicely to be beaten by 2 1/2 lengths.
Chavez was able to exploit some racing luck in finding the shortest route to the wire, which was Puzzlement's first win in six tries at the 10-furlong distance.
Puzzlement, racing fifth at the rail on the final turn, found room inside of Iron Deputy when pacesetter Blue Boat and jockey Edgar Prado floated extremely wide straightening for the stretch, taking the 4-5 favorite Volponi with him. Volponi managed to get around the fading Blue Boat in the stretch, but could not make an impact on the winner down the lane. Volponi was second for the fifth consecutive time this year.
Blue Boat set moderate fractions of :23 4/5, :48, 1:11 4/5 and 1:37 while tracked closely by Volponi, who was wide into the first turn as well.
Harlan's Holiday, the 5-2 second choice ridden by John Velazquez for record-setting Saratoga trainer Todd Pletcher, faded out of contention on the final turn.
Winning his third career race at Saratoga in five starts, Puzzlement earned $180,000. Overall, he's won five times in 19 outings with career purses totaling $572,590.
The Florida homebred is out of the dam Taine, by Sir Ivor.
Off at 6-1, Puzzlement paid $15.80, $4.60 and $3.20. Volponi returned $2.50 and $2.10. Iron Deputy, who was ridden by Jose Santos, showed for $3.80. The $2 exacta was worth $34.40.