Amidst controversy, Stephen Jackson has consistently maintained his ruthless personality both on and off the court. His leadership skills earned him the nickname Captain Jack, with 2× NBA All-Star Baron Davis once describing him as, “He was our leader.” Even a decade after his retirement, Jackson’s intensity continues to leave an impact. More recently, on 45-year-old comedian Roy Wood Jr. who revealed an unforgettable encounter that left him in awe of Jackson’s competitive spirit.

Interestingly, Stephen Jackson himself shared the clip on Instagram, captioning it, “@roywoodjr u got me [laughing emojis] my bad fam. We only know one speed. Go hard or go home.” In the video, Roy Wood Jr. recounted his experience at a recent celebrity softball game, and when asked how it went, his immediate response was, “Never again.” Intrigued, the host pressed for details, leading to a hilarious story.

During the game, Wood Jr. played as the left fielder when a fly ball came his way. While focusing on the ball, he suddenly heard grunting noises and saw Stephen Jackson sprinting toward him, or in Wood’s words, “he came out like Jeter.” His immediate thought then was, “He’s not going to stop; he’s Stephen Jackson, he’s locked in.” At the last moment, Wood had to dodge out of Jackson’s way, who indeed made the catch. Mimicking Jackson’s reaction, Wood humorously imitated, “I got this, this what I do.”

Adding to the comedy, the host explained that Wood was fielding on the left and Jackson was supposed to be at shortstop, yet Jackson sprinted across the field just to make the catch. Captain Jack’s competitive edge, honed during his NBA career where he won a championship with the San Antonio Spurs in 2003, was evident even in a friendly game Wood’s words insinuated. “There is an intensity with professional athletes even if they are not suiting up anymore,” he said, recalling Jackson was stretching, ready for the competition.

Reflecting on the incident, Wood shared his candid reaction: “And I’m like, who the f*** you talking to? It’s just you and me out here.” He then admired Jackson’s mentality, admitting he couldn’t match that intensity, a sentiment echoed by the host, who agreed, “Neither do I.”

Stephen Jackson and his ruthless mentality

In that video, Roy Wood Jr. also shed light on Captain Jack’s mentality and why he stands apart from the rest. He pointed out that while most people treated the exhibition match as fun, Jackson approached it with serious intent. “Stephen Jackson and Matt Barnes took this game so seriously, and I have nothing but the highest of respect for them,” Wood said, highlighting their dedication to winning.

Moreover, Wood described Jackson’s determination from the moment he entered the locker room. Captain Jack had his own matching Jordan shoes and outfit, rejecting the one that provided for the game. This detail underscored Jackson’s mindset: it didn’t matter whether the game was for pay or just an exhibition—his approach remained the same.

Interestingly, this intense mentality isn’t new for Jackson. During the 2009-10 season, Tyson Chandler recalled a time when Jackson even trash-talked 6× NBA champion Michael Jordan. At a Charlotte Bobcats practice, the then 47-year-old MJ, a majority owner, joined the session and told Jackson he would never be like him, which ignited Jackson’s competitive fire. “Stak [Jackson] was across the gym screaming at MJ. I was like, ‘I don’t think Stak gonna be here tomorrow,'” Chandler recounted.

The two [Jordan and Jackson] would go on to have a 1 vs 1 match, with Jackson taking a hit and though not for the beef, it did become the 2003 champion’s last season with the Bobcats.