The Classic was part of an eight-race series that matched horses bred in California and Florida. The races were split between California's Santa Anita Park and Gulfstream.
The 8-year-old Best of the Rest moved past a horse half his age in Booklet and covered the 1 1/8-mile distance in 1:49.44.
"He's had four knee injuries and if he hadn't had the surgeries, he wouldn't be racing today.."
Best of the Rest has won 14 of 27 career starts, including the Unbridled Handicap at Gulfstream last spring. He paid $9, $4.80 and $3.80.
"I always want to cry when he wins," owner Bea Oxenberg said. "If you had to overcome all the adversity this horse has, then you would know."
Booklet, who won the Grade I Fountain of Youth at Gulfstream last winter, started from the outside 12th post and finally took the lead at the top of the stretch before fading.
Booklet paid $7.60 and $5.80. Grey Meno showed for $6.80.
Continental Red, considered the best of the California-bred horses in the Classic, was a disappointing eighth.
The main race at Santa Anita was the $750,000 Distaff, where Smok'n Frolic upset Cee's Elegance to win the 1 1/6-mile race in 1:43.40