"I really relish where I'm from. That's something I really hold myself accountable with," Bailey said.
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He's staying in the South Loop near the Wintrust Arena to attend the NBA pre-draft camp. While he grew up in Chicago, he spent the last few years playing basketball in California, first at Sierra Canyon High School and last season at UCLA. Now, he's back in his hometown, on the verge of realizing the dream he's had since he was a little boy.
"This is a very exciting time. I've really put in the work to het here, and just let the chips fall where they may. Whatever happens, happens," Bailey said.
From the first time the basketball coach at Skinner West Elementary School saw then-second-grader Bailey, he realized he had a talented player. Bailey quickly began playing with much older kids and held his own.
Brandon Lomax coached Bailey through eighth grade, and stays in regular contact with him.
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"You could tell right away he was special," Lomax said. "Whoever gets this kid is gonna get a real talent, and he can flat-out play basketball."
Bailey played just one season at UCLA. After carefully weighing his options, he decided he is ready for the next challenge and to match skills with the best players in the world. Many basketball experts predict he is likely to be picket in the first round, but where he winds up is a big question.
"Whoever picks me, whoever sees the something in me where I could make an impact and be part of the team, that's where I'd like to go," Bailey said.
Wherever he winds up, Bailey said his Chicago roots will always be an important part of who he is.