Jessie attended Yuma High School where he was a three-sport athlete: all-division in basketball, all-state in football and track & field. After high school, he initially enrolled at Arizona Western College, before transferring to Imperial Valley College, where he played as a wide receiver and was a part of the track & field squad. Jessie received a scholarship from the University of Kansas where he also practiced both sports. He was a part of the school's national championship track team in 1969, while winning the NCAA indoor long jump championship with a leap of 25–2.5 and receiving All-American honors. In other track meets, he high jumped 6–6 and was timed at 13.8 seconds in the 110 metres hurdles. In football, he played running back in the same backfield with John Riggins and was also used as a split end. He finished with 33 receptions for 644 yards, more than 1,500 total yards in offense and 5 touchdowns. In 1970, he set a school record with 494 kickoff return yards. In 2010, he was inducted into the Imperial Valley College Hall of Fame.
As a rookie, he contributed mainly on kickoff returns. The next year, he became a starter at wide receiver and the team's deep threat, which included an 82-yard touchdown reception. On April 8, 1974, he signed with the Birmingham Americans of the World Football League, but the team folded before he could report. He finished the season ranked as the sixth leading wide receiver in the NFL with 761 yards and fourth in receptions. The courts ruled in favor of the National Football League Players Association and a new form of free agency was briefly instituted in 1975. After playing out his contract, he was signed by the Los Angeles Rams, but then commissioner Pete Rozelle mandated the team to send the Lions their number one draft choice along with Cullen Bryant as compensation. Bryant filed for a temporary restraining order from the courts and would never play for the Lions. The Lions eventually traded the Rams first round draft choice to the Chicago Bears, in exchange for their first and third round pick.
Los Angeles Rams
His best season was in 1976, when he was voted to the Pro Bowl after registering 34 receptions for 779 yards and 6 touchdowns. The next year, he was placed on the injured reserve list after suffering a knee injury against the San Francisco 49ers. In 1979, he was placed on the injured reserve list after suffering a broken leg against the New Orleans Saints, that also prevented him from playing in the 31–19 Super Bowl loss to the Pittsburgh Steelers. On July 31, 1980, he was traded to the Buffalo Bills in exchange for a seventh-round draft choice.
Buffalo Bills
Jesse was used in a reserve role during his 2 years with the Buffalo Bills.