Derek Anderson, an NBA champion and member of the legendary 1996 Kentucky Wildcats, offered a candid look back at his career, detailing his experiences playing with Michael Jordan, learning under Gregg Popovich, and his role in launching a classic Jordan Brand sneaker.
Playing with His Airness: Rookie Nerves and the Bulls
As a rookie on the 1997-98 Cleveland Cavaliers, Anderson was uniquely prepared to face the championship-era Chicago Bulls. He was already working out with Michael Jordan after signing with his shoe brand, which helped temper the nerves.
The first time the Cavs played the Bulls, Chicago was without Scottie Pippen, and the Cavs won easily. The second matchup in Chicago, however, was “different.”
“I felt like that it was eight people on the court; like, the smoke from the starting lineup… I wouldn’t say that I was nervous, but I was definitely not the same as the first game.”
Anderson noted that the ’97–’98 Bulls, in the early part of the season, were still finding their rhythm without Pippen, emphasizing that teams in the NBA often don’t truly “play really hard until the playoffs.”
The Genius of the Spurs and Tim Duncan’s Temper
Anderson described his time with the San Antonio Spurs as his “all time favorite” NBA experience. In 2000-01, the Spurs were the number one team in the league, winning 62 games, and Anderson was the second-leading scorer behind Tim Duncan.
“It was so refreshing to play with a guy like Tim. He would say, ‘DA, we’re going to throw you the ball.’ We didn’t have egos, Coach Pop was cool and everything was perfect so I never experienced that.”
While Tim Duncan was known for his quiet demeanor, Anderson did recall seeing him get mad at an official, though Duncan always maintained control. Duncan would simply say things like “Y’all are pitiful…” under his breath and would “pull himself back.”
The Evolution of Big Men and Rasheed’s Uniqueness
Anderson drew a clear line connecting the big men of his era to today’s stars, specifically naming Arvydas Sabonis and Rik Smits as the predecessors to Nikola Jokić.
“Absolutely. I would DEFINITELY say that. Arvydas was the BEST big man passer that I have ever played with and he was so smart… They definitely paved the way for Jokić and they let them know that he can shoot.”
However, when asked if any current player reminds him of his former Portland Trail Blazers teammate, Rasheed Wallace, Anderson was emphatic: “NOBODY reminds me of Rasheed Wallace. Nobody. Not close.”
He praised Wallace’s versatility: “He shot left-handed 3’s, right-handed 3’s, he ran the break, guarded point guards… he did everything and he was a great teammate. Nobody’s close to Rasheed. Rasheed’s different man. He had it all.”
The Business of Basketball: From Cleveland to the Clippers
Anderson reflected on the challenge of building continuity in the early 2000s, especially with the Cleveland Cavaliers. Despite making the playoffs in his rookie year—a feat the team didn’t repeat until LeBron James’ arrival—the team quickly disbanded. “Back then everybody was looking at cap than the player… so every year they would trade guys that could’ve helped you win but they were worried about the cap more back then.”
Similarly, his year with the Clippers felt like a temporary stop for a young team with no leadership. They didn’t feel like the Lakers’ “little brother” because everyone knew their contracts wouldn’t be renewed: “We were like, ‘Hey. We’re not even going to be here long, so we won’t be their little brother. We’re going to play basketball and then we’re gonna leave…'”
The Low-Cut Legacy of the Jordan XI
Anderson revealed his role in popularizing the low-cut version of the Air Jordan XI (often called the Concords).
Sitting at a meeting with Jordan and legendary designer Tinker Hatfield, Anderson simply suggested: “I would like to play in these in low cuts.”
“It wasn’t like that I was a genius person but I wanted to say, ‘Hey. I want these in three-quarters because I played in low cuts in college. I played in low cuts in high school and if I get to have my shoe, I want to play in low cuts.'” His suggestion led to an entire line of low-cut models, which he wore throughout his career.
He considers Ray Allen and Mike Bibby his biggest competitors for the best “shoe game” during his era.
On the Modern NBA
Anderson made a clear distinction between his generation and today’s league, arguing that the lack of “buddy-buddy stuff” made the game “straight BUSINESS” back then.
He views the modern NBA as more of a “show than actually a showcase,” pointing to the freedom players have to dribble the clock out or take long-range shots that were once considered “dumb shots.”
He also compared two of the game’s greatest talents, Dirk Nowitzki and Giannis Antetokounmpo, calling them “two different players.”
“If you’ve ever looked at his teams, he’s always had good players around him from Michael Finley to Steve Nash to Jason Kidd… I think Dirk was always a great player and because he had great players around him it showcased his talent.”
Conversely, he believes Giannis is a “freak of nature” who would dominate on any team, adding that the true measure of a “dominant” player, like Shaquille O’Neal, is when rival teams are built and recruited specifically to stop them—a phenomenon he believes Giannis is only now achieving.
