Gragson's great-grandfather, Oran K. Gragson, served as mayor of Las Vegas, Nevada from 1959 to 1975, making him the longest-serving holder of that office. His grandfather and father were both prominent real estate developers in Las Vegas. Gragson struggled in school due to dyslexia and a learning disability; in seventh grade he was sent to attend the Army and Navy Academy in Carlsbad, California for two years. He subsequently attended Bishop Gorman High School in Las Vegas for two years and completed his high school education online through K12. He enjoys downhill mountain biking and describes himself as an avid video game player.
Gragson started racing Bandoleros at the Las Vegas Motor Speedway Bullring at age thirteen before moving to late models. He also competed in the INEX Legends car racing series, winning the 2014 Young Lion Road Course championship.
In 2015, Gragson joined Jefferson Pitts Racing in the NASCAR K&N Pro Series West (now the ARCA Menards Series West) in the No. 7, sponsored by AlertID. He finished third on debut at Kern County Raceway Park and took his first career win battling teammate Gracin Raz at Tucson Speedway. Later in the season at Meridian Speedway he recorded his first pole position and led 176 laps to win again. He finished second in the final points standings behind Chris Eggleston with two wins, seven top fives, eleven top tens, and was named Rookie of the Year — the ninth driver in series history to finish runner-up in points and win that award simultaneously. He also ran two races in the NASCAR K&N Pro Series East that season, finishing eighth on debut at Watkins Glen International. In 2019 he made a one-off return to Jefferson Pitts Racing in the West Series at Sonoma.
In 2015 Gragson drove the No. 78 Ford Fusion for Mason Mitchell Motorsports at Kentucky Speedway, finishing fourteenth. In 2016 he made two ARCA starts: a 30th-place result at Pocono with Mason Mitchell Motorsports and a 5th-place at Kansas with Venturini Motorsports. In 2017 he competed in five races with Venturini Motorsports, with a best finish of fourth at Chicagoland. In 2018 he made two starts for DGR Crosley in the No. 54 Toyota Camry: seventh at Daytona and a pole position followed by a tenth-place at Pocono after dominating much of the early going. In 2024 it was announced Gragson would return to ARCA for Rette Jones Racing in the No. 30 at Watkins Glen International.
In preparation for the 2017 season, Gragson drove the No. 18 Toyota from Kyle Busch Motorsports at Phoenix International Raceway and Homestead-Miami Speedway, in an entry fielded by Wauters Motorsports. He was hired by Kyle Busch Motorsports on 7 October 2016 to compete full-time in 2017. His first career Truck Series win came at Martinsville Speedway in the Texas Roadhouse 200, passing Matt Crafton for the lead on the outside with ten laps to go. He finished tenth in points that year.
In 2018 he returned to the No. 18 KBM truck. A week after contact with Johnny Sauter ended his chances at Dover with two laps to go, Gragson dominated at Kansas in the 37 Kind Days 250, leading 128 of 167 laps for his second career win. During qualifying at Pocono Raceway he fell ill and was not cleared to race; Erik Jones replaced him and he was granted a playoff waiver. He also won the 2018 Snowball Derby in his final KBM ride, holding off Ty Majeski. In the same year he gained additional seat time through starts in the NASCAR Pinty's Series and began working with a sports psychologist. He finished second in the Truck Series points standings after finishing third at Homestead. In 2017 he also won the Winchester 400 in late model competition.
Gragson made his NASCAR Xfinity Series debut in the No. 18 for Joe Gibbs Racing at Richmond Raceway in 2018 as part of a three-race schedule that also included Talladega Superspeedway and Dover International Speedway.
On 25 September 2018, JR Motorsports announced Gragson would drive the No. 1 Chevrolet full-time for 2019, replacing Elliott Sadler. On 25 January 2019 the team reassigned him to the No. 9, with Michael Annett taking the No. 1. Gragson opened his rookie season with an eleventh-place finish in the NASCAR Racing Experience 300 at Daytona International Speedway, then scored a third-place at Las Vegas for his first top-five. He qualified for the playoffs through seven top-fives and seventeen top-tens in the regular season but suffered his first Xfinity DNF at the O'Reilly 300 at Texas Motor Speedway after contact with Harrison Burton's No. 18 on lap 150 spun him through the frontstretch grass for a 30th-place finish.
In 2020 Gragson won the season-opening NASCAR Racing Experience 300 at Daytona. At the Alsco 300 he was involved in a physical altercation with Harrison Burton after pushing him into the wall in the closing laps; neither driver was reprimanded by NASCAR. He finished fifth in points that year.
In 2021 Gragson was retained for a third season. At Atlanta's race that year he was involved in a fight with Daniel Hemric following a pit road incident; neither driver was reprimanded. On 10 May he finished fourth at Darlington but was disqualified when his car failed post-race inspection for unapproved suspension mounts. JR Motorsports filed an appeal, which was won, restoring the fourth-place and awarding him the $100,000 Dash 4 Cash bonus. He won at Darlington and Richmond to make the playoffs, then scored a win at Martinsville to reach the Championship 4 for the first time, finishing third in points.
In 2022 Gragson began with a third-place at Daytona and added wins at Phoenix, Talladega, and Pocono. At Road America he had an on-track altercation with Sage Karam that triggered a thirteen-car pileup on lap 25; he was fined $35,000 and docked thirty driver and owner points. At the September Darlington race he won a three-car battle with Sheldon Creed and Kyle Larson in the closing laps. He then won four consecutive races at Kansas, Bristol, and Texas, becoming the first driver since Sam Ard in 1983 to win four straight Xfinity Series races. He won his eighth race at Homestead to make his second straight Xfinity Championship 4 but finished second in the championship to Ty Gibbs.
In 2024 Gragson returned to the Xfinity Series part-time with Rette Jones Racing's new No. 30 car in four races — Charlotte, Nashville, Michigan, and Darlington — in the team's Xfinity Series debut. RJR formed an alliance with Stewart-Haas Racing for their Xfinity program. He finished in the top ten at Charlotte and top five at Nashville.
On 14 January 2021, Beard Motorsports announced Gragson would attempt the Daytona 500 in the No. 62 Chevrolet. He failed to set a qualifying time after failing inspection three times and started the Bluegreen Vacations Duel from the back; a crash with Garrett Smithley and Brad Keselowski ended his chances. He returned to Beard for the 2022 Daytona 500 and successfully qualified. He also shared the Kaulig Racing No. 16 Cup car with A.J. Allmendinger and Daniel Hemric in 2022. In his 2022 Daytona 500 start he was involved in a multi-car incident with ten laps to go while running seventh, triggered by Kevin Harvick. At the 2022 Coke Zero Sugar 400 he recorded a then Cup career-best finish of fifth. Gragson also drove the Hendrick Motorsports No. 48 at Talladega, the Charlotte Roval, Las Vegas, Homestead, and Martinsville as a substitute for Alex Bowman, who sustained a concussion from a crash at Texas.
On 10 August 2022, Gragson was announced as driver of the No. 42 for Petty GMS (later rebranded Legacy Motor Club) for 2023 on a two-year contract, replacing Ty Dillon. He started the season 24th at the 2023 Daytona 500. At Kansas he was involved in a physical altercation with Ross Chastain following an on-track incident. At Gateway he suffered a hard crash due to a brake rotor failure — his car spun toward the apron and then back up the track, hitting the wall first with the rear then the front; he experienced concussion-like symptoms and was replaced by Grant Enfinger at Sonoma.
On 5 August 2023, NASCAR and Legacy Motor Club suspended Gragson indefinitely for violation of Section 4.4.D. of the NASCAR Rule Book (member conduct) after he liked an offensive meme on social media related to the murder of George Floyd. On 10 August 2023, Gragson requested release from his LMC contract to focus on the reinstatement process. On 12 September 2023, NASCAR lifted the suspension and cleared him to resume racing after he completed diversity and inclusion training. During the suspension period he drove for Rette Jones Racing in late models and the NASCAR Canada Series.
On 13 December 2023, Gragson signed a multi-year deal with Stewart-Haas Racing to drive the No. 10 starting in 2024. He began the season ninth at the 2024 Daytona 500. After Atlanta, the No. 10 received an L1 penalty and was docked 35 owner and driver points for unapproved roof rails found in pre-race inspection. He finished sixth the following week at Las Vegas and scored a career-best third at Talladega. On 28 May 2024, Stewart-Haas Racing announced it would shut down NASCAR operations at the end of the season.
On 10 July 2024, Gragson signed a multi-year deal with Front Row Motorsports. On 3 January 2025, FRM announced he would drive the No. 4 car.
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