DDSCB25: Superstar
May 1, 2025:
Okay, if you’re a college hoops fan you know who I am but I’ll do the biography thing anyway.
Today is my 23rd birthday.
My name is Jess Ulysses Wynn. Yeah, Jess U. Wynn. My dad thought he had a sense of humor. But then his name is Roscoe so…
I had a great childhood. I was interested in learning about just about everything from a very early age. I was also interested in sports.
For my ninth birthday my parents bought me my first basketball. I’d played a lot of baseball and soccer but no hoops. After my birthday party, which was on a Saturday afternoon, my Uncle Kip said, “Let’s go outside and try this new ball.”
Kip was a terrific athlete, the best golfer and bowler in the area. He had made all state in high school hoops. I didn’t know that at the time but I did know he was a great athlete.
My dad had put up a hoop in the driveway at as close to exactly 10 feet high as possible.
So Kip and I went outside. He spent a good hour teaching me how to dribble, roll the ball off my hand, notice where it lands and where it comes back up to… Then he spent another hour teaching me how to shoot- roll the ball off my palm, keep my elbow tight and my wrist locked… Then he had me shoot from various positions on the court, long shots, medium shots, layups… and critiqued my shooting.
Finally, he taught me the basics of playing D. We covered a LOT in one session and we didn’t quit until mom called us into dinner. Kip was a bachelor and he ate with us often. He was kind of on the strict, serious side, but he knew his stuff and I wanted to learn so I didn’t mind when he was hard on me.
At dinner dad asked how I did.
“He’s got the makings of a basketball player. If he wants it enough to put in the time he could be good.”
That was music to my ears and I spent that whole next week practicing everything he taught me and trying hard to get it all right.
The next weekend he was at the house both days and we spent every moment on the court. I loved it even when he yelled at me, which he did.
We practiced hoops every weekend when it didn’t rain, until it got too cold and icy. I DID play Little League and go to the practices but that was mostly on weekdays. When it rained on the weekend Kip would give me indoor “skull sessions,” talking about every conceivable situation that could come up in a game.
By the time I could actually play in a league, on my middle school team as a 12 year old 7th grader, I was six feet tall. Naturally the coach wanted me to play Center but Kip said no to that. He insisted that I play the 2 spot, shooting guard.
“Long term this kid is a guard and that’s where he plays or he doesn’t play at all.”
The coach agreed with the proviso that I played in the middle on D late in close games. Kip agreed to that.
I guess I was a natural shooter, and with the help I got from Kip I made it count, averaging more than 25 a game- and our games were only 24 minutes long. Despite playing SG I led the team in rebounds, also in assists and steals. My team won the league title.
The following year was even better. We went undefeated. By the end of my eighth grade year I was 6’ 4” tall. I never grew at all after that but that’s a good height for a shooting guard.
It was the same argument in high school. The coach wanted me to play Center and Kip said no. This coach didn’t budge so Kip talked to the coach in the next town, where he lived. The guy said if I played for him he’d let me play SG. I moved in with Kip and played at that school for 4 years. The original school fired their coach after my freshman year but I stayed where I was anyway.
I made all state honorable mention as a freshman, averaging 28 points and 14 RBs.
My 2nd, 3rd, and 4th year we won the state title. I made all state all 3 years and was statewide player of the year in my junior and senior years.
During my freshman year I picked up a nickname, “Glass.” I LOVE to shoot bank shots and I hit them at an unbelievable 72%. I almost can’t miss off the glass. Thanks to Uncle Kip for that as well.
Starting in my freshman year scouts came to my games, talked to me, called my house… even though I made it clear to all of them that I was going to UConn, no doubt in my mind.
By my junior year pro scouts were talking about me going pro right out of high school. Not a chance. 1) I HIGHLY value education. 2) I don’t EVER plan to play pro ball. I want to coach at the college level. The travel as an NBA player is way more than I want, and I want to get a head coaching job as soon as possible.
High school ball was fun. We thought Coach Casey pushed us hard but later, when I was at UConn, it became clear that Coach Casey hadn’t pushed us very hard. Coach Calhern REALLY pushed us!
My first year at UConn went great. We got to the national semifinal and I was named a 2nd team All American. Once again the pro scouts came calling and I ignored them. The NIL came in and I made some very good money. I knew that my first head coaching job wouldn’t pay much so the NIL money would really be great.
The next three years we won the national championship all three times and I was named national player of the year all three times. I was being talked about as one of the greatest college hoops players of all time. Thus the title here, "Superstar." That really didn’t mean much to me.
The NIL money came to a little over 2 mill by the time I graduated. That’s after taxes. So I'm all set financially.
My UConn career averages were 30.3 points and 14.7 RBs, 10.2 assists. So I averaged a triple double for my career!
Uncle Kip made it to all of my home games for all 4 years, usually with Dad.
College hoops was fantastic. I had great teammates and all of the coaches were terrific. I learned a lot but mostly I really loved playing. I know I’ll miss it but I want to coach. My mind is clear about that.
During my senior year I applied for grad school at UConn, enrolling as a Masters student. Coach signed me as a graduate assistant coach, which was awesome.
Coach. I haven’t said much about Coach Calhern. He was VERY tough and VERY demanding but he clearly was a “player’s coach” despite that. He had our backs at all times. And he knew the game incredibly well. Playing for him and coaching under him taught me an incredible amount.
My graduate year we went to the Elite Eight and I thoroughly enjoyed coaching. In the Spring Coach put in a good word for me at several schools concerning head coaching jobs. He convinced a few of them that I was ready.