Tyler Gaffalione achieved two significant career firsts in 2023 that played a role in him being voted an Eclipse Award finalist for outstanding jockey. Gaffalione won his first Kentucky Oaks in May, when he guided Pretty Mischievous to a neck victory in the filly classic. By year’s end, Gaffalione had compiled $29,980,952 in mount earnings, which represented his highest total since he began riding in 2014. Gaffalione’s mount earnings ranked second among North American-based riders in 2023. He won 23 graded stakes, which was fourth among all riders. Of those victories, six came in Grade 1 races. :: Full list of 2023 Eclipse Awards finalists, including profile stories Pretty Mischievous overcame post 14 to win the Kentucky Oaks. “I’m so happy I was able to accomplish this, especially being in my home track now, Churchill Downs, and my family is here today,” Gaffalione, a 28-year-old Florida native, said in a post-race press conference. “It’s a dream come true for me. I grew up in this business. I idolize these guys I’m now riding with and competing with. It’s hard to put into words. I just feel so blessed to be given these opportunities.” Gaffalione won two additional Grade 1 races aboard Pretty Mischievous last year, the Acorn at Belmont Park and the Test at Saratoga. Gaffalione also won Grade 1 races last year with Caravel, Gina Romantica, and Gunite. Overall, Gaffalione won 270 races in 2023, third best in North America and one off his career-high of 271 in 2020. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.