In January 2010, Jackson Bend finished second in the grade three
Holy Bull Stakes at
Gulfstream Park at a mile on the dirt. In February, he was second in the
Grade II Fountain of Youth Stakes at a mile and one eighth at Gulfstream behind
Eskendereya. In April, he stepped up in class and ran second again to Eskendereya in the
Grade I $750,000
Wood Memorial Stakes at
Aqueduct Racetrack in New York at a mile and an eighth. After five wins and three graded-stakes placings, owner Robert LaPenta and trainer Nick Zito ran him in the second jewel of the Triple Crown, the $1,000,000
Preakness Stakes a
Grade I at
Pimlico Race Course at a mile and three sixteenths on dirt. Jackson Bend broke well and stalked the leaders in third behind
First Dude and
Kentucky Derby winner
Super Saver passing the grandstand for the first time. He continued in third along the rail down the backstretch. Around the final turn,
Eclipse Champion Lookin At Lucky and
Caracortado passed him on the outside. Coming down the lane, Jackson Bend swept across five paths to the outside, passing Super Saver and Caracortado. In the final 1/16 of a mile, he continued to close on the leaders and finished third by less than a length to winner Lookin At Lucky, finishing a nose behind second-place First Dude. == Four-year-old season ==