MILWAUKEE — Sidney Moncrief was always more than a basketball player to me. Growing up in Milwaukee, I went to many Milwaukee Bucks games during Moncrief’s era from 1979-89).
Through 10 seasons with the team, he averaged nearly 4 assists per game, shot more than 50% from the field, and scored at a clip of almost 17 points per game.
At a glance, maybe not knock down stats, but the five-time All-Star — was also a defensive stopper (2-time NBA Defensive Player of the Year) — and the consummate player-coach, always talking, helping teammates and playing the game the right way.
Those are the qualities that drew me to him… and, the fact that when I was 10 years old, he took the time to respond to a letter that I wrote to him. He answered my questions: “Where’d you go to college? What are my chances of making the NBA?,” and one more question that I don’t remember, on two 3×5 cards and provided an autograph – all via U.S. mail.
My chances of making the NBA answer, by the way, he told me: ”1 in a 1,000,000.”
Frankly, I thought he was being generous with those odds.
Fast forward to 1998, when Moncrief was inducted into the Wisconsin Athletic Hall of Fame, I was a consultant with the hall and got to write the inscription on his plaque and walk him to the stage. So, of course, I quickly told him the story of how I still cherished the fact that he returned my fan mail – but didn’t tell him about the Bucks Photo Day polaroid of him and me. You can see it here:

Now 67, Moncrief is still coaching. After a successful business career, he’s writing books, teaching leadership lessons, consulting with businesses and talking about the game that’s given him and his family so much. His new book, is “The G.R.I.T. Kids Teach Grandpa Sid the Biz.”
He’ll debut it at Dr. Martin Luther King Jr. School, 3275 N. 3rd, tomorrow. It’s an engaging story that introduces students to what Moncrief calls the five literacy superpowers – speaking, talking, listening, writing, and researching.
On Friday, Moncrief will meet with college and high school students at ThriveOn King during “30 for 30 Shadow a CEO” – a program that pairs students with some of Milwaukee’s top business leaders for hands-on mentorship in leadership, entrepreneurship, and workplace readiness.
Moncrief joined The Upswing on Wednesday, hear our conversation here.