Shepherd grew up in Ajax, Ontario, where he played youth football with the Ajax/Pickering Dolphins Football Club.
College career
At Simon Fraser University, Shepherd redshirted his first year and was able to start every game his second year as a defensive end. He left the university after a total of two years, as he wasn't able to pay tuition. After leaving Simon Fraser, Shepherd spent time at working various jobs including at a plant nursery, electrical construction, and a boxing factory. Fort Hays State University later reached out to Shepherd, and Shepherd was able to pay his first semester of tuition before being put on athletic scholarship. After his 2017 season, Shepherd was named the MIAADefensive Player of the Year. He was also invited to play in the 2018 Senior Bowl.
Professional career
On November 20, 2017, it was announced that Shepherd had accepted his invitation to play in the 2018 Senior Bowl. He became the first player from Fort Hays State to receive an invitation to the Senior Bowl. Shepherd was productive during Senior Bowl practices and had his draft stock rise significantly after displaying speed, power, and technique while going up against the top offensive linemen in the nation. Shepherd unfortunately suffered a broken hand during Senior Bowl practice and was unable to participate in the official game. Shepherd attended the NFL Scouting Combine in Indianapolis and completed the majority of combine drills, but opted to skip the bench press due to his fractured hand. His performance continued to raise his draft stock and garnered him attention throughout the draft process. On March 12, 2018, Shepherd held a pro day at Fort Hays State, but opted to stand on his combine numbers and only performed positional drills for the scouts and team representatives from 16 NFL teams that attended. Shepherd attended ten private meetings with team and also performed at private workouts for multiple teams, that included the Dallas Cowboys, Arizona Cardinals, Atlanta Falcons, and Houston Texans. At the conclusion of the pre-draft process, Shepherd was projected to be a second or third round pick by NFL draft experts and scouts. He was ranked as the sixth best defensive tackle prospect in the draft by DraftScout.com and Scouts Inc. The New York Jets selected Shepherd in the third round in the 2018 NFL Draft. Shepherd was the sixth defensive tackle drafted in 2018 and became only the third player to be drafted in the history of Fort Hays State. He became the first player to be drafted from Fort Hays State since Frankie Neal was drafted by the Green Bay Packers in the third round of the 1987 NFL Draft. On May 14, 2018, the New York Jets signed Shepherd to a four-year, $3.87 million contract that includes a signing bonus of $987,724. Shepherd was suspended for six games for violating the NFL's performance-enhancing drugs policy on September 10, 2019. It was revealed that Shepherd underwent a sports hernia surgery in the off-season plus battling a shoulder issue and a herniated disc in his back. Shepherd confessed about using the PEDs in an effort to speed up his recovery, which eventually led to his suspension. He was reinstated from suspension on October 29, 2019, and was activated on November 1, 2019.
