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The NCAA tournament is where legends are born.

Bryce Drew’s buzzer beater for Valparaiso? Check. Derrick Rose nearly clinching a title for Memphis in 2008? Double check. Illinois’ run to the title game in 2005, with its miraculous comeback against Arizona in a regional final? Triple check.

Even if they never play another minute of basketball, we can relive their accomplishments each spring. RedEye talked to a pair of Chicago hoops legends about March Madness memories, and how they’ve become difference-makers off the court.

Jack M Silverstein is a RedEye special contributor. Say hey @readjack.

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KHARA SMITH

Then: The Proviso West grad became a three-time All-American at DePaul, helping lead the Blue Demons to four tournament appearances.

Now: Smith teaches autistic children in Aurora.

DePaul’s women’s program has earned 11 straight trips to the NCAA tournament, including this year. But the Blue Demons have reached the Sweet 16 only once, in 2006. Khara Smith did her part, averaging 15.7 rebounds in three games that tournament.

Tell us about your senior year, when you finally made it to the Sweet Sixteen.

[The game against Tulsa in the second round of the 2006 tournament] was an up-and-down game. I believe we were down the whole game and then in the last two minutes of the game we got on a roll. I got an important and-1 in the last couple minutes that put us over the hump, and we finally got to the Sweet Sixteen.

What was it like going back to campus?

It was really exciting because everybody was excited to be able to say that we were the first team to do this in school history. And then in the Sweet Sixteen, to be able to play an elite team like LSU, it was just overall excitement and enthusiasm to be able to be there. It was a great campus experience, with everybody supporting us.

After I graduated, I decided not to play [in the WNBA]. My body was banged up, and I was just kind of tired. I ended up having my first son in 2007, so I had to reprioritize. I got into education working with at-risk youth. I worked with an afters-chool program tutoring and mentoring at-risk youth, and then a couple years ago I moved to Aurora, where now I’m teaching at Aurora Education Center, an alternative school for autistic and behavioral kids.

Was there anything you learned in basketball that helps you as a teacher?

A lot of teachers at the school say I have a lot of patience, and I think that coming from a large family and then going into college where there are a lot of personalities and talents on the basketball court [builds patience]. And then remaining humble and sharing [my success] with my teammates, because if it wasn’t for them, I wouldn’t be that player. I try to carry that over [to teaching], especially the patience part, just because with the behavioral and autistic kids, you just never know what to expect on a daily basis. So patience I think is the most important one.

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BOBBY SIMMONS

Then: He averaged 13.6 points and 7.5 rebounds per game over three years at DePaul.

Now: Simmons runs Succezz Clothes in the South Loop, as well as other businesses.

When Simeon’s Bobby Simmons joined fellow Chicagoans Quentin Richardson and Lance Williams at DePaul, the city buzzed with excitement—the Blue Demons were back. Now running several businesses, Simmons, 32, talked about DePaul’s performance in the 2000 NCAA tournament against Kansas, a first-round exit.

What stands out in your NCAA tournament experience?

Bus ride to the game: total silence … total silence. Everyone had headphones on. Coaches weren’t talking. Get to the locker room, and now everybody’s going through game plans, scouting reports, getting prepared. Warmup was pretty intense. Coach [Pat] Kennedy gives us an overview of everything that we need to do.

So we play the game, and we played very well, to be honest. We just fell short on one play, and it sticks out. [Point guard] Rashon Burno throws a cross-court chest pass. [Laughs.] Kenny Gregory drives down. [Shooting guard] Paul McPherson chasing him. And they called an and-1 when Paul didn’t even nearly look like he touched him. It’s like, “Oh man.” Now we gotta chuck a shot, and it doesn’t go in, and that’s the end of our season.

Tell us about founding Succezz Clothes and your other businesses.

Succezz started with myself and Lavelle Sykes. When I was in DePaul, he ran a store called Tony’s Sports. I was like, “Well, I love fashion, I love sneakers, he’s done it for numerous years. How about I provide a business here in the city of Chicago?” This came about in 2008. Spectrum Printing was in 2008. Simmons Entertainment, 2009. [Simmons also runs Society Nightclub.] They all work together.

The violence that goes on in the city, it hurts. It really hurts. Because you can’t save everybody. And that’s why I have all my businesses here—because I want to show kids you don’t have to be a basketball player to be successful. That’s why the name is “Succezz.” I always tell them, “Our success is in our daily routine. If you put forth the effort to be the best at whatever it is you want to be, you will be successful because you are working at it. You are passionate enough about it to make sure that it doesn’t fail.”

Jack M Silverstein is a RedEye special contributor. Say hey @readjack.