He played college football for the Northern Colorado Bears, and was selected by the San Diego Chargers in the second round of the 2005 NFL draft.

[5] A straight-A student in high school, Jackson was accepted to Columbia, but decided to attend University of Northern Colorado on a partial scholarship to play both basketball and football.

[7] Jackson also started for Northern Colorado in basketball,[9] playing for two seasons at UNC and leading the team in scoring both years.

[10] Jackson was selected in the second round (61st overall) of the 2005 NFL draft (the highest ever by a Northern Colorado graduate) by the San Diego Chargers.

[18] By virtue of the release of Keenan McCardell and an injury to Eric Parker,[19][20] Jackson entered the 2007 season as a starting wide receiver for the Chargers.

[citation needed] He started the season in an unmemorable fashion in a home game against the Chicago Bears by dropping a sure touchdown that bounced off his chest in the end zone.

[citation needed] However, by the end of the season, Jackson had distinguished himself as a top target for Chargers quarterback Philip Rivers.

Jackson received an unsportsmanlike conduct penalty for kicking the challenge flag, which cost the Chargers 15 yards (the play was upheld).

[27] He was handcuffed briefly and had his car impounded following a traffic stop just a few hours before the Chargers' playoff loss to the New York Jets.

[30] Jackson had a strong showing in his first Pro Bowl appearance, racking up seven receptions for 122 yards, including a 48-yard catch and run for a touchdown.

Initially, Adam Schefter of ESPN reported that Vincent Jackson wanted compensation in the form of $10 million or to become an unrestricted free agent when the lockout was over.

[citation needed] Jackson's decision to drop his alleged request of unrestricted free agency and/or monetary compensation helped expedite the completion of the new labor deal.

[44] When the NFL's Collective Bargaining Agreement expired, Jackson became a Restricted Free Agent for an additional year, causing the Chargers to place a one-year, $3.2 million tender on him.

[46] On August 20, 2010, the Chargers placed him on the Roster Exempt List, meaning that he would have to serve a three-game suspension once he had agreed to a contract.

[58] At the conclusion of a 4–12 season, Jackson proved to be one of the few bright spots on a football team in disarray, compiling 78 catches for 1,224 yards and seven touchdowns.

[59] The 2014 season saw declines in Jackson's catches and yards due to the emergence of rookie wide receiver Mike Evans.

[63] On October 18, 2016, Jackson was placed on injured reserve after suffering a knee injury in Week 5 in a win against the Carolina Panthers.

[67] He sponsored military families at every Buccaneers home game through the 'Jackson in Action' Front Row Fans section at Raymond James Stadium.

[69] On February 17, the sheriff of Hillsborough County announced that Jackson's family said he may have suffered from chronic alcoholism, which contributed to his death.

[74] On December 22, the Hillsborough County Florida Medical Examiner concluded that official cause of Jackson's death was chronic alcohol use.