2021: Two-year-old season

Jack Christopher began his racing career on 28 August in a Maiden Special Weight event over 6 furlongs at Saratoga Race Course. Starting as the 11/10 favorite in a field of 7, he began sharply and forged three wide on the turn entering the straight, where he kicked clear, winning by 8+3⁄4 lengths.^[4] Trainer Chad Brown then entered the colt in the Grade I Champagne Stakes at Belmont Park. Nearly five weeks later, Jack Christopher was made the heavy favorite over Gunite and Wit. The latter had won the Grade III Sanford Stakes and was the only other stakes winner in the field.^[3] Gunite shook free in the early going to take the lead, but Jack Christopher moved quickly into a stalking position. He pulled away and never faced a serious challenge, winning by 2+3⁄4 lengths in a time of 1:36.72.^[3] Jack Christopher earned points for the Kentucky Derby as well as automatic entry for the Breeders' Cup Juvenile held at Del Mar.^[3]

However, Jack Christopher was scratched the day before the Breeders' Cup Juvenile on the advice of Breeders' Cup veterinarians. Due to a couple of areas lighting up on a bone scan, mainly the left shin, he had a screw inserted in that shin by orthopedic surgeon Dr. Larry Bramlage and was sidelined for two months.^[5]

2022: Three-year-old season

Jack Christopher resumed training after his operation on 27 February in Florida, which was deemed too late for preparations for the Kentucky Derby. After gradual training of ten spaced works, connections entered Jack Christopher in the Pat Day Mile Stakes over a distance of one mile on the Kentucky Derby undercard.^[6] Jack Christopher was made the 7/10 favorite in a field of eleven three-year-olds. After pressing the pace of early leader Pappacap, he pulled away to score by 3+3⁄4 lengths in a time of 1:34.81. Trainer Chad Brown commented, "It's a little bittersweet that we did get him to the first Saturday in May, which we had been thinking about since he debuted up at Saratoga, that unbelievable performance. To get him to the first Saturday in May and have him roar down the stretch and get to the winner's circle but not be in the race that's a few races later, will always be in the back of my mind if he could have done it."^[7]

On 11 June, Belmont Stakes Day, Jack Christopher was entered in the Grade I Woody Stephens Stakes, a sprinting event for three-year-olds. Once again he dominated the field, winning his fourth straight event and second Grade I with a ten-length victory.^[8] Jack Christopher pressed leader Provocateur through a half-mile in :45.38 before being pushed for more in early stretch. He then drew off under a hand-ride in the last 100 yards, completing the seven furlongs in 1:21.18. Trainer Chad Brown commented after the event, "I felt really good when Jose (Ortiz Jr.) slipped to the outside of the speed horse. The only thing I was worried about was Provocateur potentially really hounding us the whole race; potentially softening us up from a tricky post. Once Jose got him out in the clear, I didn't see any possible way this horse could lose."^[8] After the win, connections indicated that Jack Christopher would attempt to run at a longer distance and challenge the premier three-year-olds.

He was then entered in the Grade I Haskell Stakes at Monmouth Park in his first attempt in an event with two turns and at a distance of 1+1⁄8 miles. Jack Christopher was installed as the 7/10 favorite in a field that included GI Arkansas Derby winner Cyberknife and Bob Baffert-trained Grade I Santa Anita Derby winner Taiba. Jack Christopher began well, rated off of longshot Benevengo entering the clubhouse turn. He stalked close up two wide, then pressed the pace, bid two wide entering the far turn, dueled on the turn, put a head in front at the quarter pole, and was overtaken by Cyberknife and Taiba to finish third, beaten by two lengths.^[9] Winner Cyberknife set a track-record of 1:46.24 for the 1+1⁄8 miles distance.^[10] Chad Brown was positive after the race, saying, "I felt very, very good turning for home. I thought it was a beautiful trip, but at the end of the day, I thought he (pushed) fair fractions. It's pretty simple we have to cut him back. Hats off to the winner. He looked the part of a real threat the entire race."

On August 27, Jack Christopher returned to a sprinting event, the seven-furlong Grade I H. Allen Jerkens Memorial at Saratoga. Starting as the overwhelming favorite at 11/20, he bounced in front but then conceded the lead to Conagher. With three furlongs to run, Ortiz guided Jack Christopher guided to the front and held Gunite off for a 1+1⁄4 lengths victory in a time of 1:21.15. Brown said, "I'm just so proud of the horse. He's been a very consistent horse. He's never disappointed us in a workout or a race." He was noncommittal regarding what might be next for his trainee, but the Grade I Breeders' Cup Sprint and Grade I Breeders' Cup Dirt Mile appeared to be options that fall at Keeneland.^[11]