ELMONT, N.Y. – In the coming months, Javier Castellano may have a difficult decision to make, whom to ride between Kentucky Derby winner Mage and Belmont Stakes winner Arcangelo, should they show up in the same race such as the Travers Stakes on Aug. 26 at Saratoga. Two summers ago, a struggling Castellano had an even more difficult decision to make – continue riding or retire. A winner of four consecutive Eclipse Awards – 2013-16 when he averaged 329 wins and $26.4 million in purse money won – Castellano’s business had tailed off. In late 2020, a year in which he missed time due to COVID, Castellano underwent hip surgery. Trying to return in one of the toughest jockey colonies around – one with Irad Ortiz Jr., Jose Ortiz, Luis Saez, and Joel Rosario – was challenging. Wins were not coming as frequently as frustration. At age 43, was it time to retire? “Two years ago, I was struggling. Mentally, I was ready to give up and walk away,” Castellano said Sunday morning. “I was upset because I knocked on the door of every single stable, every single barn, and I don’t see any feedback at all. I thought maybe this is it. The summer of 2021 I was really, really depressed. “I talked with my family and my family support me in my career and they said if it’s time go that’s okay, we are here,” Castellano said. :: Take your handicapping to the next level and play with FREE DRF Past Performances - Formulator or Classic.  At the 2021 Saratoga meet, Castellano won just 13 races. In 2013 at Saratoga, he won 66 races, the second-most of any rider in that track’s history. With more time to think, Castellano wasn’t ready to walk away. At the end of the 2021 Saratoga meet, he retained P.J. Campo as his agent. Campo, a former racing official at the New York Racing Association and Gulfstream Park, had helped Eric Cancel win the 2020-21 Aqueduct winter title. “I back up a little bit. I regrouped in my mind I said I better keep pushing and see how far you can go,” Castellano said. “Little by little, doors opened. I went out of town, started winning races, and I started developing my business for the following year.” Castellano won three races on opening day 2022 at Saratoga and finished the meet with 25 wins. He finished the Belmont at Aqueduct meet with 27 wins, second in the standings. He was fourth in the Aqueduct fall standings and sixth at the Gulfstream winter meet, while getting more opportunities. The last five weeks have seen Castellano win his first Kentucky Derby aboard Mage and then, Saturday, his first Belmont Stakes on Arcangelo. Castellano had been a combined 0 for 29 in those two races. “Dream come true,” Castellano said. “That’s what I’ve been waiting for a long time.” Castellano became the first jockey to win Triple Crown races on two different horses in the same year since Calvin Borel in 2009. That year, Borel rode Mine That Bird to a huge upset in the Kentucky Derby, then took off that horse to ride the fabulous filly Rachel Alexandra to victory in the Preakness. Those two horses never ran in the same race, so Borel never was faced with any decision. Mage and Arcangelo both have the Travers penciled in on their schedules, and it’s also possible they could run in the Jim Dandy on July 29. Castellano, who is 1 for 3 on Mage and 3 for 3 on Arcangelo said it will be a hard decision if it comes to that. “They’re both good horses, I think we’ll wait as long as we can,” said Castellano, who holds the record for Travers wins with six. With that, Castellano excused himself as there was another horse to work, an unraced 3-year-old named Big Night Out, for trainer Barclay Tagg. For Castellano is once again a jockey in demand. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.