Before his breakthrough in South Texas, Jackson arrived in Houston for the 1995, 1996 campaign. The Rockets were coming off back-to-back NBA championships, looking for inexpensive floor spacers who could play alongside Hakeem Olajuwon and Clyde Drexler. Jackson suited up in Houston Rockets jersey No. 13, appearing in 42 regular-season contests.
Jackson made an immediate impression by knocking down 35.5% of his three-pointers and providing physical backcourt defense off the bench. While Houston ultimately restructured its roster that offseason to acquire Charles Barkley, Jackson's stretch with the Rockets verified his capability as a legitimate rotation guard on contending squads.
That short season in Houston established the exact archetype Gregg Popovich sought two years later in San Antonio: a low-maintenance, veteran shooter with the discipline to fit seamlessly into high-stakes playoff schemes.
