[11] Following a commitment to join the University of Arizona, Jackson was deemed academically ineligible due to his low SAT and ACT test scores.

[15] Jackson's strong play, and particularly his fearlessness against the Suns' Cedric Ceballos, is largely what led to team president Danny Ainge drafting him months later.

He was juiced at practice ready to play and compete and make the starters better, and it carried over into his second year when he got his opportunity to get out onto the floor and prove he could be a vital part of the organization.

[28] Following the 2003–04 NBA season, he was traded to the Indiana Pacers[29] for power forward Al Harrington (who finished 2nd place in Sixth Man of the Year voting), after signing a 6-year, $38.3 million contract.

[33] A series loss in the next round at the hands of the Detroit Pistons ended their season, with Jackson leading the team in scoring during the playoffs with an average of 16.1 points per game.

Jackson, who was on probation in Michigan after pleading no contest to misdemeanor assault and battery charges there for his part in a brawl, fired several gunshots from a 9-mm pistol, he asserted as an act of self-defense.

[38] He pled guilty to a felony count of criminal recklessness, received one year of probation, and was ordered to pay a $5,000 fine and perform 100 hours of community service.

[41] Along with Al Harrington, Šarūnas Jasikevičius, and Josh Powell, Jackson was swapped for Mike Dunleavy, Troy Murphy, Ike Diogu, and Keith McLeod of the Warriors.

[43] On February 5, when Golden State traveled to Conseco Fieldhouse to compete against Jackson's former team, he tallied 36 points and led the Warriors to a 113–98 victory over the Indiana Pacers.

[44] Jackson joined Vince Carter and Dominique Wilkins as the only players in 25 years to amass 30 or more points against a team that they played for earlier in the season.

[52] Jackson struggled due to the defensive tandem of Andrei Kirilenko and Matt Harpring and his offensive output decreased from the previous series.

[53] Prior to the 2007–08 NBA season, Jackson (along with guard Baron Davis and forward Matt Barnes) was named a team captain of the Warriors.

[54] Jackson was the recipient of the NBA's Western Conference Player of the Week award (November 26 – December 2), averaging 23.0 points, 5.5 rebounds, 3.8 assists, and 2.8 steals.

[59] Jackson's 2008–09 campaign effectively ended when he decided to determine the root cause of turf toe on his left foot, which had been ailing him for over 2 years.

[61] His per-game season averages were 20.7 points, 5.1 rebounds, 6.5 assists (2nd only to LeBron James for forwards), 1.5 steals, and 39.6 minutes (2nd in the league, trailing only Joe Johnson of the Atlanta Hawks).

[64] In tandem with forward Gerald Wallace, Jackson led the Bobcats to the franchise's first playoff appearance (culminating in a 4–0 series loss at the hands of the Orlando Magic).

[66] In the 2010-11 NBA season, Jackson recorded the first triple double (24 points, 10 rebounds, and 10 assists) in Bobcats team history versus the Phoenix Suns on November 20, 2010.

As part of the terms, the Milwaukee Bucks received Jackson, Shaun Livingston, the rights to the 19th overall pick in the 2011 NBA draft, Tobias Harris from Charlotte, and Beno Udrih from Sacramento.

Due to recurring issues with his hamstring throughout the lockout-extended offseason[70] and several publicized clashes with coach Scott Skiles,[71][72][73] Jackson's role and playing time diminished.

[74] On March 13, 2012, Jackson was traded back to the Golden State Warriors along with Andrew Bogut, in exchange for Monta Ellis, Ekpe Udoh, and Kwame Brown.

[77] A re-adjustment period to San Antonio's structured offensive system caused Jackson's minutes to fluctuate in the regular season and playoffs.

Despite spurts of inefficient, turnover-prone play, Jackson proved a capable playmaking option, with above-average passing abilities and court vision.

Larry Brown, a member of the Basketball Hall of Fame and former head coach of the Charlotte Bobcats, readily acknowledged Jackson's ability: "You ask anyone in the league – Stephen is an elite player.

"[98] NBA legend and former Pacers president Larry Bird called Jackson the toughest player in the league, regarding injuries and subsequently playing through the pain.

"[102] Following a community outreach event, Gwen Knapp of the San Francisco Chronicle stated that "[Jackson] couldn't have been more charming or more engaged, the perfect face of the franchise.

"[106] Stemming from the two referenced incidents in 2004 and 2006, Jackson has pled guilty to felony criminal recklessness, and been charged with a number of misdemeanors, including assault, disorderly conduct, and two counts of battery.

[109] After receiving criticism from Naismith Hall of Fame members such as Kareem Abdul-Jabbar and Charles Barkley, Jackson apologized for his comments, saying that he "used the wrong words".

"[113] In December 2011, under the alias Stak5, Jackson released a rap mixtape entitled What's a Lockout?, hosted by DJ Scream of Maybach Music Group.

[115] Imani Showalter, Jackson's ex-fiancée and mother of two of his children, was a cast member of the first season of Basketball Wives: LA, a reality show airing on American cable television network VH1.

During his 7-game suspension to begin the 2007–08 NBA season, Jackson donated a significant portion of his time towards community service in the Oakland area, organizing several events geared mainly towards children.