LOUISVILLE, Ky. – That ear-to-ear smile that can light up a room belies what jockey Tyler Gaffalione is really feeling. For even when he wins, Gaffalione isn’t completely satisfied. “I’m never happy with where I’m at. I always want to get better, want to improve,” Gaffalione, 29, said this week. “If you’re not getting better, you’re getting worse. “I can’t tell you how many races I’ve won where I don’t want to watch it just because it was not pretty,” Gaffalione added. “Some of my biggest wins.” When asked to name one from his collection of 2,311 career victories, Gaffalione paused, flashed that smile as one came to mind, but declined to describe it. “I don’t want to throw myself under the bus,” he said. Saturday, Gaffalione will have his best chance yet to win the sport’s biggest race when he climbs aboard Sierra Leone in the Kentucky Derby, a race in which Gaffalione is winless in six rides. That comes a day after he rides Ways and Means in Friday’s Kentucky Oaks, a race he won last year aboard Pretty Mischievous. Sierra Leone and Ways and Means are trained by the four-time Eclipse Award-winning trainer Chad Brown. While Brown has had a two-decade-long friendship with Gaffalione’s agent, Matt Muzikar, Brown has really been impressed with Gaffalione’s desire to improve. :: DRF Kentucky Derby Package: Save on PPs, Clocker Reports, Betting Strategies, and more. “He’s a student of the game, he’s always trying to improve his profession,” Brown said. “He’s so active trying to learn and communicate with you before and after the races and in the mornings.” That and Gaffalione’s domination of the Kentucky circuit Jockey the last four years – he’s won 10 of 12 Churchill Downs titles and six of nine at Keeneland – is why Brown plotted months ago to get Gaffalione on Sierra Leone. Brown had in mind the Blue Grass Stakes at Keeneland and then hopefully the Derby at Churchill and wanted a rider who excelled over both tracks. “Out of my choices, he’s been riding the most at these two tracks,” Brown said. “It gave me just a little bit more comfort knowing that I could commit to that over the winter and see it through to the Derby if he got to the race.” Gaffalione first rode Sierra Leone in the Risen Star Stakes in February at Fair Grounds, where he rallied from well off the pace over a sloppy track to a half-length victory over Track Phantom. In the Blue Grass, after Sierra Leone held up the proceedings by balking at the gate, Gaffalione gave another terrific ride, rallying Sierra Leone from next-to-last to a 1 1/2-length victory over Just a Touch. “He was so impressive in the Risen Star that day, making up all that ground, slow pace, sloppy track, overcame a lot,” Gaffalione said. “But I was even more impressed with him last time, with that little bit of a fit he threw behind the gate, for him to compose himself and get his mind back on running and put on the performance that he did I thought it was incredible. It just shows the mind frame that he has and the talent that he has.” Gaffalione’s grandfather Bobby rode the Kentucky Derby in 1984, finishing 10th on Rexson’s Hope. Gaffalione’s father, Steve, is also a former jockey. While he didn’t ride in the Kentucky Derby, Steve did win the 1989 Tampa Bay Derby on Storm Predictions. Tyler Gaffalione won this year’s Tampa Bay Derby on Domestic Product. Steve Gaffalione saw from a young age his son’s desire to be a top rider. Gaffalione bought his son an Equicizer, a hand-crafted mechanical horse, when he was 12 years old. On the family’s 17-acre farm in Florida, Steve said Tyler had his own makeshift jockeys’ room and silks and would ride the Equicizer with no one around for hours. He then would ask his father to come out to show him what he’d been doing. “He rode that Equicizer better than I ever could,” Steve said. “Everything you see now, he had that back then. All he did was watch videos. He loved Jerry Bailey, and Mike Smith was so great with him; he’d talk to him once a week.” Tyler Gaffalione, the champion apprentice rider in 2015, and his father often go over Tyler’s rides. Steve lets Tyler do most of the talking. :: Get the Inside Track with the FREE DRF Morning Line Email Newsletter. Subscribe now.  “Tyler’s the hardest person on himself that he could be,” Steve Gaffalione said. “He takes it to heart almost to a point you feel bad for him. He’s my son, all I can ask for in life is for him to be happy. He’s so hard on himself that I hate it myself. He wants to be the best rider he can be at all times.” Tyler Gaffalione said the area he’s constantly working on is patience. “There’s a fine line with being too aggressive and being too patient,” Gaffalione said. “Just trying to find the spot for the horse.” More often than not, these days, Gaffalione is doing just that. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.