[2] Jackson was a 6'6" (198 cm), 220-pound (100 kg) shooting guard who started all four years at Macomber High School in Toledo, Ohio.

[5] In the middle of the 1996–97 season, Jackson was traded to the New Jersey Nets along with Sam Cassell, Eric Montross, George McCloud, and Chris Gatling for Shawn Bradley, Ed O'Bannon, Robert Pack, and Khalid Reeves.

Jackson was reported to be unhappy with his reduced role and shooting while playing with Allen Iverson, who was viewed as the 76ers' franchise player.

In the middle of the 1997–98 season, the 76ers traded Jackson along with Clarence Weatherspoon to the Golden State Warriors for Joe Smith and Brian Shaw.

Although Jackson saw an increased role as the Warriors' starting shooting guard, averaging 18.9 points, 5.6 rebounds, and 40.6 minutes per game for the remainder of the 1997–98 season, he disliked playing for a losing franchise.

[citation needed] In an effort to clean up their image and team chemistry in the 1999 offseason, the Trail Blazers traded or chose not to re-sign many of their players.

Jackson, and talented but troubled Isaiah Rider were both traded to the Atlanta Hawks for Steve Smith and Ed Gray.

After voicing his displeasure with losing, Jackson was traded with Larry Robinson and Anthony Johnson in January 2001 to the Cleveland Cavaliers for Brevin Knight.

Hailing from nearby Toledo and a product of Ohio State, Jackson's trade to the Cavaliers was viewed as a homecoming of sorts.

Additionally, Jackson was happy to be part of a team that, as an early-season success story, was eyeing the playoffs for the 2000–01 season despite a run of injuries to a number of key players.

Despite averaging 13.3 points and 4.8 rebounds in 41.3 minutes per game, the Rockets dealt Jackson along with Boštjan Nachbar to the New Orleans Hornets for David Wesley.

With starting shooting guard Joe Johnson injured, Jackson stepped up his play in the postseason, helping Phoenix reach the Western Conference final.

During much of his career, Jackson wore a sweatband on his arm with the numbers "419" (which refer to the North American telephone area code 419 that serves Toledo and most of northwest Ohio) to represent where he is from.