It has taken him to University of Chicago Laboratory Schools, Illinois State University, Hofstra University and now Slovenia, where the Hyde Park native this month signed a professional contract with KK Helios Domzale.
"Words cannot describe how thrilled I am to even be able to say that I play professional basketball anywhere," Upshaw said.
Justin Breen says Upshaw was one of the most improved college athletes in the country last season:
Upshaw, a guard/forward, was the one of the first players in Lab Schools history to earn a Division I basketball scholarship when he headed to Illinois State. He now has become one of the first Maroons ballers to ink a pro deal.
His former Lab Schools coach, Troy Caldwell, isn't surprised.
"From Day One in my program, I always thought he would play professional basketball," said Caldwell, of Bronzeville. "I'm just extremely happy and excited for him and the player he's become."
Upshaw's skills were forged on blacktops throughout the South Side, in AAU ball and Small Fry leagues. His mother, Jewel, said she spent so much of her money on her only child's basketball obsession, that they once came home from a tournament in Florida to see their phone had been turned off.
"When he was a child, we were at a Toys R Us, and I couldn't find him," Jewel Upshaw said. "But I knew I would find him if I went to the area with all the basketballs, because he wasn't interested in anything else."
Upshaw was a standout hoopster at Ariel Community Academy, where he said he was mentored by Ariel Capital Management founder John Rogers and U.S. Secretary of Education Arne Duncan, also the director of the Ariel Education Initiative.
After eighth-grade graduation, Upshaw received financial assistance to attend Lab Schools.
"It was the most perfect place for him," his mom said. "He was so doubtful because it was so diverse and he didn’t come from that type of environment. They’re Labbers, and he thought he would be so out of place, but it was just the opposite. He blended right in."
As Upshaw adapted to the rigorous classwork, he also changed his name. His real name is Zena — the same name as his father — but he was teased during elementary school because his name sounded similar to the main character of the television show "Xena Warrior Princess." Before his first day at Lab Schools, Upshaw was asked what he should be called, and he chose Zeke because it sounded cool.
Upshaw was a dominant prep player. As a junior, the 6-foot-6 wingman averaged 24 points and 12 rebounds. In his final season, he was named the Independent School League's player of the year.
Upshaw expected similar success at Illinois State, but he was redshirted as a freshman, and in his three competitive seasons, he combined to average only 1.6 points per game.
Upshaw graduated with a degree in apparel, merchandising and design, and still had a year left of eligibility, which he used at Hofstra this past season. He enjoyed a rejuvenation of sorts, leading the Colonial Athletic Association with a 19.8 ppg average. His scoring increase from the 2012-13 to 2013-14 campaigns led the nation.
"Receiving a chance to play the game I love once again, one last time for Hofstra University is an opportunity I will always cherish," said Upshaw, who also is one class short of receiving a master's degree in higher education from Hofstra.
Over the summer, Upshaw and his agent, Brian Bass, looked for pro opportunities throughout the world and found the league in Slovenia that employs several other American players. Upshaw has been in Europe for a few weeks since signing the contract Sept. 1. The season begins next month.
"He’s real level-headed, he’s humble, and he understands what it’s taken to get to this point in his career," Caldwell said.
Upshaw hopes to continue his basketball dream for as long as he can. A possible career in the fashion industry — he's loved clothes since Jewel dressed him up in elaborate outfits as a baby — awaits if hoops doesn't work out.
For now, Upshaw said he's nothing but "blessed."
"Being able to make a kid smile or look up to you, or even putting on a show at a game for our fans this year will be a huge blessing to me," he said.
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