Leo High School Alumni Association Those Leo Men http://www.leoalumni.org Donald Whiteside '87 Interviewed and Written by Patrick Mc Gavin 4/10 DONALD WHITESIDE '87 The greatness of a man is measured from the neck up, Napoleon said. Donald Whiteside never commanded armies or fought in wars. He has from his early beginnings smart, shrewd and instinctive. He also was a guy that was never afraid to cut his own path. That instinctive feel for unselfishness and camaraderie has allowed for a varied and interesting life encompassing a background in athletics, academia, coaching and law enforcement. He was young man who forged an identity of work, discipline, toughness and above all else, leadership. His innate skills in sports, particularly basketball, have paved the way for a remarkable life of travel, adventure and financial independence not typically associated with somebody who spent the first five years of his life in one of Chicago’s most notorious housing projects, the Robert Taylor Homes. This man grew up largely left to his own devices, without the guidance of a male authority figure. He had his scrapes and acting out, but he also had a strong sense of decorum and right and wrong. Sports solidified him, gave his life meaning and value. It is just a part of his remarkable story. It is one very much worth telling. Origins Young Donald was born April 25, 1969. “My roots started down in the Tennessee area around Nashville,” Donald says. “My grandmother was a very inspirational person in my life. She married a man with the last name of Martin, and she had two daughters. Then she remarried a guy, John Whiteside, my grandfather, the man whose name I took. My mother was their daughter. I think my mother got a lot of her traits from my grandmother. “We started out in the Robert Taylor Homes and on my fifth birthday, we moved to Englewood area of 66th and Hamilton. My mother still owns that house. For grammar school I went to Luke O’Toole right around the corner, at 65th and Seeley. I went there for kindergarten and first grade. My mother was a single mother, and she decided to put my sister and me into a Catholic school. We started at St. Basil, on Garfield and Wood and we went there for the rest of our grammar school years. page 1 / 13 Leo High School Alumni Association Those Leo Men http://www.leoalumni.org “I was always in the neighborhood. I didn’t exactly detach myself from the neighborhood. I got into a little trouble when I was growing up. I’d carry a slingshot when I was growing up. I broke windows and threw rocks. Our house on 66th and Hamilton was a one-sided street. There were the railroad tracks on the other side, so I was always used to setting up cans and knocking cans off. When I started playing basketball, we made these homemade rims out of wood and we’d stand them in the middle of the street and we’d play full court in the middle of the street. After grammar school we’d started traveling more and playing in different parks against different people. Back then the neighborhood was a little safer. There were gangs back then, but they weren’t as bad as they are today.” He was a wisp of a kid, standing maybe five-foot tall and weighing maybe ninety-five pounds, dripping wet, as the popular saying went. He was quick, fast, alert to his surroundings and he had a direct, no-nonsense seriousness about the way he carried himself that people noticed. As the only boy in a family of four, including his mother, he was fairly solitary in his pursuits. He liked to read, and as he mentioned, play with that slingshot, but never in a malicious way. Interesting enough, the sport that would open up so many personal and career opportunities was a distant afterthought growing up. Football and basketball were his first two loves. He loved the great Pittsburgh Steelers’ wide receiver Lynn Swann, a balletic and graceful player whose spectacular play in the Super Bowls made him an athlete many young kids wanted to emulate. As a south sider he also grooved on the exploits of Harold Baines, the great left-hand power hitter of the Sox. “A bunch of the guys I used to play grammar school basketball with would say: ‘You need to come out for the basketball team.’ I’d tell them: ‘No. I’m not really interested in basketball. I don’t really like basketball.’ Eventually they convinced me to come out. This was the sixth grade. Actually I missed try outs by a day. They brought to the coach. “He said, ‘Son, tryouts were yesterday. You’re a day late. These guys said you’re okay, so I’ll give you a look.’ They put us in a 2-3 zone and all I could do was play the top part of the zone and when they tried to pass the ball to the wing, I’d shoot the gap like a cornerback and steal the ball and dribble down fast and lay it up. That became the beginning of my basketball career. The coach gave me a ride home that night, and of course he asked me why I waited so long to come out for the team. That started a great relationship with my coach, and my two best friends from grammar school, John Hamilton and Corey Walden.” He played baseball until the start of his freshman year of high school. He saw instantly basketball was his métier. This was page 2 / 13 Leo High School Alumni Association Those Leo Men http://www.leoalumni.org the sport where all of his physical and mental attributes would best be put to use. “Of course playing basketball grammar school, you go to a lot of tournaments. You go to a lot of leagues, and you play in the St. Sabina league, which is very popular. I got a lot of recognition playing in that. When it was time to go to high school, we all decided to go to De La Salle. The night before the test, my best friend called and he said he was taking the test at Leo. “And I said, ‘Well, I am too.’ We both took the test at Leo. John was a basketball player up until high school and he was very good football player. Corey didn’t grow much once he got to high school and he had to make the transition from playing center in grammar school to playing guard in high school. He ended up being a very good football player, and he went to Purdue as a cornerback. “[The Leo basketball coach] Jack Fitzgerald didn’t think I could play for him. You have to remember, I was a late bloomer physically and I was still very small. I started my freshman year at Leo, and I’d play a little open gym during recess and things like that. I impressed the guys a little. I had the bigger obstacle of convincing Fitz I could play. A prominent Leo guy, Mike Holmes said to me: ‘If you want to compete with bigger guys, you have to get stronger.’ I started doing putting push-ups and working out. That was motivation for me. I ended up going to trials, and I ended up doing well and impressing a lot of people and I ended up starting on the freshman A team. We went undefeated.” The choice to attend Leo was fortuitous for both parties. Like a lot of young men, young Donald matriculated to Leo primarily out of solidarity and friendship with his two best friends. That was perhaps the original rationale, but things had a way of naturally going the route he had hoped. “My two best friends were at Leo, and then all of the guys I played against at the St. Sabina league were there: Thor Palamore, Darryl Arnold, Asa Powell, everybody from that league went to Leo. We continued our development as basketball players there and just kind of jelled.” When Donald started at Leo in the fall of 1983, Ronald Reagan was page 3 / 13 Leo High School Alumni Association Those Leo Men http://www.leoalumni.org president, the country was finally coming out of a vicious recession and the neighborhood around the school was finishing its considerable social transformation. Demographically Leo was a racially mixed school, and basketball brought a lot of kids together, he said. To get to school he’d take the Damen bus to 79th and go east or the Marquette bus at Ashland down to 79th. His friend John Hamilton lived at 66th and Marshfield and two often planned their trips to rendezvous on their way to school. “I tried a paper boy route and I tried working at Leo, painting lockers and doing stuff like that, but once I became a ballplayer, I was so dedicated to getting better, I just never had the time to work. “I gained a lot respect very quickly, just being who I am. I’ve never been super outgoing and I’ve never been super shy. I was pretty good with people. I was not phony at all, so I made friends quickly. Leo’s always had its brotherhood. Once you became a Leo man, whether you transferred or not, you always remember that. Coming into Leo, we had guys like Marlon Maxie that went on.