He played college football for the Houston Cougars and was selected by the Cincinnati Bengals in the first round of the 2016 NFL draft.

Jackson was born on October 27, 1992, and grew up in the Fifth Ward area of Houston, Texas, alongside a brother and three sisters.

[1] He attended and played football at Wheatley High School in the city, where he was teammates with fellow NFL cornerback Xavien Howard.

[4] With a deep cornerback class going into the combine, many analysts were more focused on Vernon Hargreaves III, Jalen Ramsey, and Mackensie Alexander, regarding them as the top players at their position and had Jackson as a second round selection.

During camp, Jackson had suffered a torn pectoral muscle and would have to undergo surgery, leading him to miss his entire rookie season after he was placed on injured reserve prior to Week 1.

In Week 7, Jackson earned his first career start after Adam Jones was inactive due to a back injury.

[24] Head coach Marvin Lewis named Jackson and Dre Kirkpatrick the starting cornerbacks to begin the regular season.

[31][32] He recorded his first interception with Washington in the season opener against Los Angeles Chargers quarterback Justin Herbert.

[34] Jackson missed the final two games of the 2021 season due to a calf injury then being placed on the COVID-19 reserve list on January 5, 2022.