A native of Alva, Florida, Chastain was a watermelon farmer on his family's farm until he turned thirteen. He is a graduate of Riverdale High School in Fort Myers and attended Florida Gulf Coast University for a semester before beginning his racing career. While his father raced as a hobby, Ross is the first generation of his family to race competitively. He started racing at age twelve after seeing his father race and other kids his age competing. His home track was Punta Gorda Speedway in Punta Gorda, Florida, where he competed in both late model and Fastruck Series events. His short track career included races at Citrus County Speedway, Auburndale Speedway, and DeSoto Speedway on a tight budget—a theme that continued into his early NASCAR career. He scored over fifty wins in short track feature events, including the Limited Late Model portion of the 2011 World Series Of Asphalt Stock Car Racing at New Smyrna Speedway, winning three of eight events.
He is the nephew of Roger Chastain, a former stock car racer who passed away from COVID-19 complications in 2021, and of Jane Chastain, described in the corpus as the first Woman's Sportscaster in American History.
After relocating to Charlotte in mid-2011, Chastain took over the No. 66 Turn One Racing entry in the NASCAR Camping World Truck Series after Justin Marks vacated the seat. His first Truck race at Lucas Oil Raceway at Indianapolis was his first race with live pit stops; he finished tenth. In 2012 he competed for Rookie of the Year honors with SS-Green Light Racing in the No. 08 truck sponsored by the National Watermelon Association and National Watermelon Promotion Board, recording a best finish of third at Bristol Motor Speedway.
In January 2013 it was announced that Chastain would drive fifteen Camping World Truck Series races for Brad Keselowski Racing. At Iowa Speedway in September he took his first career Truck Series pole for the Fan Appreciation 200, led the most laps, and finished second to James Buescher in a green-white-checkered finish. He also finished second at Phoenix, leading over sixty laps, behind Erik Jones.
Chastain moved to RBR Enterprises for a part-time 2014 Truck schedule but was released from the ride following comments and racing actions at Martinsville. He made his debut in the Nationwide Series (now Xfinity Series) at Charlotte Motor Speedway in the No. 55 for Viva Motorsports that year, and also drove for Hattori Racing Enterprises, delivering that team's best NASCAR finish. He joined JD Motorsports in 2015, replacing Jeffrey Earnhardt, and logged four top-ten finishes in the Xfinity Series including a ninth at the season-opening PowerShares QQQ 300.
Chastain's 2017 Xfinity season was the best of his career to that point, scoring a top-five at Iowa and two top-tens, finishing thirteenth in points—the highest position among non-playoff drivers. The season included fights with Jeremy Clements at Bristol and with Brendan Gaughan at Texas, the latter resulting in a post-race brawl behind Victory Lane in which a JD Motorsports crew member, teammate Garrett Smithley, was hospitalised with a head injury. In 2017 Chastain also made his Monster Energy NASCAR Cup Series debut, driving Premium Motorsports' No. 15 at Dover, finishing twentieth.
In 2018 Chastain ran the full Xfinity season with JD Motorsports alongside a part-time Cup schedule with Premium Motorsports. Chip Ganassi Racing (CGR) agreed to a three-race arrangement in the Xfinity Series for races at Darlington Raceway, Las Vegas Motor Speedway, and Richmond Raceway. At Darlington, Chastain claimed pole over Christopher Bell and won the first two stages before an incident with Kevin Harvick, who subsequently parked in Chastain's pit stall and made heated public comments. At Las Vegas Motor Speedway, Chastain led all but twenty of the 200 laps and won the DC Solar 300 over Justin Allgaier, his first victory in over 200 NASCAR starts. He smashed a watermelon on the track as part of the victory celebration. The win secured his first career Xfinity Series playoff berth. Chastain was eliminated from the playoffs after the opening round when Matt Tifft claimed the final spot by three points at Dover.
Chastain joined Niece Motorsports for the No. 45 Silverado part-time in the Truck Series and ran 30 Xfinity races with JD Motorsports' No. 4, supplemented by three races with Kaulig Racing's No. 10. On May 10, 2019 he won his first career NASCAR Gander Outdoors Truck Series race, the Digital Ally 250 at Kansas Speedway, inheriting the lead from Stewart Friesen after Friesen ran out of fuel. He nearly forfeited a win at Iowa, where he led 141 of 200 laps and swept the stages but failed post-race inspection; the victory was forfeited to Brett Moffitt under NASCAR's newly introduced disqualification policy, making Chastain the first driver to have a win revoked since Dale Jarrett in 1995. His appeal was denied. He won the following week at Gateway's CarShield 200, leading 21 laps and pitting for only fuel on his final stop. He also won the Circle K Firecracker 250 at Daytona for Kaulig Racing; teammates Justin Haley and A. J. Allmendinger finished behind him, though Allmendinger was subsequently disqualified. Chastain won at Pocono Raceway in the Truck Series, dedicating the win to Kaulig crew chief Nick Harrison, who had died the previous week.
Chastain broke the all-time NASCAR record for most consecutive races run across all three national series to start a season through the LTi Printing 250 at Michigan, totalling 36, surpassing Kyle Busch's mark of 22 set in 2008.
Chastain drove for Kaulig Racing full-time in the 2020 Xfinity Series. He returned to the Cup Series at the Daytona 500 and Coca-Cola 600, driving the No. 77 in a partnership between Chip Ganassi Racing and Spire Motorsports. He also retained a Truck Series role with Niece Motorsports in a part-time capacity. On February 19, 2020, Roush Fenway Racing named Chastain as replacement driver for an injured Ryan Newman in the No. 6 Ford, driving three Cup races before the COVID-19 pandemic halted the season; Newman returned when racing resumed.
On September 21, 2020, Chip Ganassi Racing named Chastain as the driver of the No. 42 Chevrolet in 2021, replacing Matt Kenseth. Chastain's Cup tenure with Ganassi began with a seventh-place finish in the 2021 Daytona 500, his best Cup finish to that point, and he finished a career-high seventh in the Xfinity standings with 27 top-tens—the most of any driver that season—and fifteen top-fives. On June 30, 2021, co-founder Justin Marks announced that Trackhouse Racing had purchased Chip Ganassi Racing's entire NASCAR operations after the 2021 season, leaving Chastain as a free agent. On August 3, 2021 it was revealed that Chastain would drive the No. 1 Chevrolet Camaro ZL1 for Trackhouse Racing's second Cup team alongside Daniel Suárez's No. 99 in a multi-year deal beginning in 2022.
Chastain scored his first career Cup win at the Circuit of the Americas, battling Alex Bowman and A. J. Allmendinger. A month later he claimed his second victory at Talladega. He finished third at the Phoenix finale and second in the points standings.
At the 2022 Xfinity 500 at Martinsville Speedway, Chastain was in tenth place on the final lap and needing to advance into the Championship 4. He drove his car into the outside wall in Turns 3 and 4, reaching speeds of up to 130 miles per hour (210 km/h), overtaking Denny Hamlin and four other drivers to finish fifth (subsequently moved to fourth after Brad Keselowski was disqualified post-race for his car being found underweight). The move set a record for the fastest lap during a NASCAR Cup Series race at that track. Chastain stated the move was inspired by playing the video game NASCAR 2005 on the GameCube as a kid with his brother Chad. Hamlin, who was eliminated from the playoffs as a direct result, described it as "a great move", adding "when you have no other choice, it certainly is easy to do that." The move was dubbed the "Hail Melon"—a portmanteau of the Hail Mary pass in American football and "watermelon" in allusion to Chastain's background. Within days, footage received more than 100 million views on Twitter and other social media. NASCAR ruled the maneuver legal but banned it the following season, indicating future occurrences would result in a time penalty.
During the season Chastain also developed a feud with Denny Hamlin, which began at Gateway in June when Chastain ran into Hamlin's back bumper causing a spin, and escalated through subsequent incidents at Atlanta.
Chastain won at Nashville for his first win of 2023. He was eliminated from the Round of 12 at the Charlotte Roval but won the season finale at Phoenix, finishing ninth in the points standings. Shortly after finishing fifth at Kansas, Noah Gragson confronted Chastain over a racing incident; Gragson shoved Chastain, who retaliated with a punch to the face.
Despite four top-fives and nine top-tens during the regular season, Chastain went winless and missed the playoffs for the first time since 2021. During the playoffs he won at Kansas, holding off William Byron. Following the Martinsville playoff race, the No. 1 was docked 50 owner and driver points and Chastain and the team were each fined US$100,000 for race manipulation, after Chastain and fellow Chevrolet driver Austin Dillon formed a blockade to allow William Byron to make the Championship 4; a team member named Surgen was suspended for the Phoenix finale. In the Truck Series, Chastain returned to Niece Motorsports to win at Darlington.
Chastain started the 2025 season with a 40th-place DNF at Daytona. At Charlotte three months later he ran down and passed the dominant William Byron with five laps to go, scoring his first win of the season and becoming the first driver in the modern Cup Series era to win a race in which he started last. He was eliminated from the Playoffs following the Charlotte Roval.
This article is based solely on the supplied corpus. No external sources were consulted; claims that could not be substantiated against the corpus were omitted under the drop-the-claim rule.
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