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On February 1, 2020, Lockwood became the fastest PBR rider to cross the $4 million dollar mark in earnings. Lockwood earned the $4 million dollars in his first 39 months of competing in the PBR.

On March 1, 2020, during the championship round of the Caterpillar Classic in Kansas City, Missouri, Lockwood hung his spur in the bull rope while getting off I'm Legit Too after completing a 91.5-point ride aboard the bull. Lockwood's left hamstring was torn from his hip bone requiring surgery and a six-month recovery. At the time of his injury he led the PBR with 9 round wins and had five 90 point rides in the 2020 season. Lockwood was World Number 2 in the standings before the injury.

On February 9, 2019, while attempting to ride Wild Goose, Lockwood was struck in the shoulder by one of Wild Goose's horns. This resulted in a broken collar bone that took Lockwood out of competition for nine Unleash the Beast events. At the time of the injury, he was ranked number one in the world with a lead of 967.5 points. On October 4, 2019, at the Minneapolis Invitational, Lockwood set a new PBR record for the most 15/15 Bucking Battle wins in a single season. He rode Bad Beagle for a score of 91.5 for his fourth 15/15 Bucking Battle win of the season.

On October 13, 2019, in Greensboro, North Carolina, he selected Heartbreak Kid for the championship round of the Wrangler Long Live Cowboys Classic. Heartbreak Kid was on the second longest buck-off streak in PBR history. He had 38 constitutive buck-offs at PBR premier series events. Lockwood broke the buck off streak when he made eight seconds scoring a new career high 93.75 points. When Lockwood released the rope at the end of the ride, he crashed into the arena floor head first. There was no celebration by Lockwood as he immediately exited the area in pain after the potential neck breaking landing. He was diagnosed with a cervical sprain. The following weekend, Lockwood rode Heartbreak Kid again at the Cooper Tires Take the Money and Ride in Nampa, Idaho, for a new career-high 94 points. On November 8, 2019, during a ceremony at the PBR World Finals, Lockwood received the Mason Lowe Award for his 94 point ride on Heartbreak Kid. Two days later, he won the PBR World Finals event average and his second world championship.

Lockwood’s annual rankings in his career to date are as follows:

After dating for more than a year, Lockwood announced his engagement to World Barrel Racing Champion Hailey Kinsel in March 2019. He lives on a two-hundred-acre ranch he purchased in 2019, which is near where he grew up. Lockwood's younger brother, Jake, is also a professional bull rider on the PBR tour. Professional Rodeo Cowboys Association National Finals Rodeo Average Champion barrel racer Lisa Lockhart is Lockwood's aunt. On October 25, 2019, Jess Lockwood and Hailey Kinsel were married at Kinsel's ranch in Cotulla, Texas. The Lockwoods split their time between their ranches in Stephenville, Texas, for the winter and Montana for the summer.

In the 2018 season, Lockwood's bid to win back-to-back World Champion titles was cut short when a groin injury left him unable to compete in the final six regular-season premier series events. On September 7, 2018, Lockwood limped from the arena after riding Power Puff for 70 points. He declined the re-ride and was unable to compete in the remainder of the event due to the groin injury. Lockwood did not compete again until the PBR World Finals on November 7, 2018.

He was named the PBR 2016 Rookie of the Year. Early in the 2017 season, he missed five events due to a groin injury when he was stepped on by 2015 PBR world champion bull Long John. On September 9, 2017, while attempting to ride Sweet Pro's Bruiser, Lockwood was knocked unconscious. On September 23, 2017, he was stepped on by Blue Magic after being thrown. Lockwood suffered a punctured lung, four broken ribs, and a lacerated kidney. After missing several events due to these injuries, Lockwood still finished 2017 a winner. In Las Vegas, Nevada, at the T-Mobile Arena, on November 5, 2017, he became the youngest bull rider in history to win the PBR World Champion title and was awarded the $1 million prize that goes with it.

Lockwood joined the PBR on his 18th birthday, September 28, 2015.

Jess Lockwood (born September 28, 1997) is an American professional bull rider on the Professional Bull Riders (PBR) tour. He joined the PBR in 2015 and was named Rookie of the Year in 2016. On November 5, 2017, he became the youngest PBR World Champion. He won his second PBR world championship on November 10, 2019. He also became the youngest bull rider to win two world championships.

Jess Lockwood was born on September 28, 1997, in Volborg, Montana, to Ed and Angie Lockwood (née Schillinger). His father was a former Big Sky region champion bull rider and a professional saddle bronc rider. His mother was a long-time barrel racer. Lockwood was raised on his family's 12,000 acre ranch where they run about 400 head of cattle. As a small child, he would crawl on his father’s back and be bucked around their living room for eight seconds. He would then ask his mother “How many was I?”. His father would then interview him using the TV remote as a microphone. Lockwood said his father taught him to ride first on sheep and calves, then steers and bulls. Lockwood started riding bulls when he was in the 8th grade. He was the Northern Rodeo Association year-end champion in 2014 and 2015, earning $60,000 in his junior year of high school. He completed his senior year of high school on-line in order to pursue bull riding full time.