He had one of the greatest basketball careers for the Ohio State Buckeyes and would be the first guard taken off the board in the 1992 draft, shortly after hall of famers like Shaquille O’Neal and Alonzo Mourning. But from the beginning he painted himself in a negative as he held out for the majority of his rookie season for the Dallas Mavericks. The next two years looked promising as they drafted Jamal Mashburn in 1993 and Jason Kidd in 1994 to create their Three J’s trio. But after two years of improvement and big playoff dreams going into 1996, an early season with Kidd, Jackson and singer Toni Braxton led to a love triangle that destroyed a young team with so much potential. And Jackson’s career would never be the same after this as over the 10 years he would play for 11 teams and never be able to recreate his individual success in Dallas. He struggled with knee pain throughout his career and always seemed to be on losing teams. But just as it seemed his career would be over, he re-invented himself as a 3 and D player and became one of the best 3 point shooters in the NBA for a a 5 year stretch. And he would end his career with 4 straight playoff appearances where he would be a valuable postseason performer every time. It’s hard to put a grade on Jim Jackson’s career due to so many variables and you can’t help but wonder if he is “what if” who could have been a starter if circumstances were different or if he was a player who excelled on bad teams, but was better suited as a role player on good teams. But regardless, he kept his career alive for nearly a decade in a half to become on the greatest Journeymen in NBA history.

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