[20] He was brought in by coach Fotios Katsikaris to replace the club's legend, Javi Salgado, with a more athletic and dynamic play-maker, a decision that earned critics from fans and observers.

[21] A frosty reception awaited Jackson in Spain, having to adapt to the competition level, considered the best national domestic league in Europe, and his dual role as facilitator and crunch time scorer, he had ups and downs before becoming the focal point of his team, leading them to 6th in the league before having a decisive role in their run to the playoff final, beating powerhouse Real Madrid in the process.

[25] His second season in Spain was as successful, being named the fifth best point guard in the Liga ACB[26] as he led his team to another playoff appearance though this time they lost in the first round, Jackson top scoring for Bilbao in both games.

[33] At the beginning of the season Jackson found himself behind Miloš Teodosić and newly arrived Jeremy Pargo in the rotation, playing most of his minutes as a shooting guard, for instance in the October exhibition game against the Minnesota Timberwolves.

[34] When Teodosić got injured in March 2014, Jackson was chosen to replace him,[35] playing nearly 31 minutes per game in the EuroLeague quarter-finals against Panathinaikos, though he finished with only 5.4 in PIR.

[36] Teodosić reclaimed his place after healing and Jackson barely featured in the semi-final meltdown loss to Maccabi Tel Aviv,[36] he even picked up a knee injury late in the game,[37] which kept him out of the Red Army club's consolation come from behind title in the VTB United League.

Jackson repaid that faith with a strong start to the 2014–15 season, including a stretch in December that saw him nominated for the VTB United League Monthly Award.

[42] He also had a decisive contribution in the EuroLeague victory against Anadolu Efes Istanbul in January, scoring 21 points without missing a single shot along with 4 rebounds and 4 assists to finish behind teammate De Colo in the Top 16 Round 3 MVP rankings.

[43] In a rotation system with De Colo, Teodosić and Sonny Weems occupying either the point guard, shooting guard or small forward positions,[44] Jackson was often a substitute, however he had important contributions when called upon, for example in another EuroLeague semi-final loss to Olympiacos, where his 7 steals broke the Final Four single game record,[45] with 9 points, 3 assists for 1 turnover and 4 fouls drawn he was the third best rated player in that game.

[46] Jackson was credited as "one of CSKA's best players down the stretch" in the VTB United League playoffs, posting 8.7 points, 6.1 assists and 1.8 steals per game whilst playing more minutes (24.5) and being seen as more effective than fellow guards De Colo and Teodosić.

The Moscow club finished unbeaten in the playoffs to win the 2014–15 VTB United League as Jackson contributed 12 points and 8 assists in the final series Game 3 against Khimki.

[50] Near the end of the 2017–18 NBA season, Jackson would sign a contract with the Houston Rockets, replacing the position previously held by Tim Quarterman.

On December 16, 2019, Jackson signed with Maccabi Tel Aviv of the Israeli Premier League for the rest of the season, joining as an injury cover for John DiBartolomeo and Nate Wolters.

[62] With his great quickness and ball handling,[63] he can create his own shot, and is adept at getting to the basket to finish around the rim, with either hand, and often in acrobatic fashion, even through contact.

[64] It was noted in 2009, that he could improve his decision making skills, ball-handling, mid-range jump shot, and defensive fundamentals, whilst highlighting his effort and potential.

[68] On September 17, 2006, Jackson and four other Duquesne teammates Sam Ashaolu, Stuart Baldonado, Shawn James and Kojo Mensah were the victims of an unprovoked shooting on the university's Pittsburgh campus.

Ashaolu was shot in the head and neck, Mensah in the shoulder and arm, Baldonado through his back into his elbow, James in his left foot whilst Jackson was only grazed on the wrist by a bullet.