In March 2017, I sat down with NBA champion Derek Anderson on Scoop B Radio for a “buttoned-up” look at his journey from the University of Kentucky to the rough-and-tumble NBA of the late 90s. While Anderson is often remembered for his smooth scoring and elite athleticism, he revealed a side of his rookie self that many fans might have missed: absolute fearlessness. Specifically, Anderson recounted his mindset when facing the legendary Patrick Ewingand the New York Knicks—a team that defined “intimidation” during that era.
“I Always Tried to Dunk on Him”
When Anderson entered the league with the Cleveland Cavaliers in 1997, the Knicks were still the enforcers of the Eastern Conference. Patrick Ewing was the ultimate gatekeeper of the paint. While most rookies would steer clear of the Georgetown legend, Anderson had a different philosophy.
“I always tried to dunk on Patrick Ewing,” Anderson told me. “I didn’t care who it was. I watched Michael Jordan do it, and I felt like if you were going to be great, you had to challenge the best. Patrick was the biggest, baddest dude in the paint, so that’s who I went after.”
Anderson’s mindset was a reflection of the “Jordan Era” influence. He saw MJ’s iconic 1991 baseline dunk over Ewing not as an impossible feat, but as a blueprint.
The “No-Fly Zone” of the 90s
Our conversation touched on just how physical the NBA was before the “freedom of movement” rules of the 2020s. Anderson noted that trying to dunk on someone like Ewing or Charles Oakley came with a physical tax.
“They didn’t just let you go up. You were going to get hit. Hard,” he remarked. “But that was the beauty of the game then. You earned every bucket.”
The Kentucky Pedigree of Confidence
Anderson credited his time at Kentucky under Rick Pitino for giving him the “audacity” to challenge NBA legends. Being part of the 1996 “Untouchables” team meant playing with a target on your back every night. By the time he reached the NBA, the bright lights of Madison Square Garden didn’t blind him—they motivated him.
2025 Retrospective: The “Key One” Returns
As we discussed earlier, Derek Anderson’s talent evaluation skills have remained sharp into 2025, specifically regarding his early “call” on De’Aaron Fox (who is currently leading the San Antonio Spurs to a #1 seed trajectory). Anderson’s own career was a testament to the fact that speed and confidence are a timeless combination.
| Derek Anderson Career Milestone | Achievement |
| 1996 NCAA Champion | Key member of the Kentucky “Untouchables.” |
| 1997 NBA Draft | 13th overall pick to the Cleveland Cavaliers. |
| 2006 NBA Champion | Won a ring with Dwyane Wade and Shaq on the Miami Heat. |
| 2025 Status | Motivational speaker and author of Stamina. |
As Anderson told me:
“You can’t be afraid to fail on the big stage. If you’re afraid to get blocked, you’ll never get the dunk.”
In 2025, that “Stamina” mindset is exactly what he teaches the next generation of athletes. Whether it’s a rookie trying to dunk on a legend or a veteran like Fox navigating a new system in San Antonio, the foundation is the same: Zero fear.
