EXCLUSIVE Derrick Rose Interview Former MVP on his Past, Present & Future

It was in mid-November when the SLAM crew flew into Chicago for the main photo shoot of this special issue. There, at Simeon Career Academy, we shot the cover of this magazine with Derrick Rose, as well as other solo shots in different looks, which you’ll find sprinkled throughout these pages. But what had initially started as just planning for a D Rose shoot in the weeks leading up to that day became a much bigger operation thanks to Rose’s vision and commitment to his community. 

He asked that the current players at Simeon, his alma mater, be included in the shoot. And
not just the varsity squad—freshman and JV, too. And, so, after we finished solo shots with Rose, about 40-ish teenagers arrived to join the Bulls legend in a media day-type set up that included photo and video stations. Except, when they first arrived, they had no idea what they were about to partake in. 

Looking to surprise the kids, Rose’s team and Simeon varsity head coach Tim Flowers, who was Rose’s teammate and starting center when both played for the Wolverines in the mid 2000s, decided not to tell the players in advance why they were being asked to come down to the school on a Saturday afternoon. After Rose was done with his solo shots, he walked up to a classroom where the players had been asked to gather and surprised them with a visit. Rose made sure to go around the room and individually dap up every single player before stopping at the center of the classroom and delivering an impromptu, off-the-dome speech. A raw and candid talk with them about life, mistakes, obstacles and the challenges that they’re facing in the South Side of Chicago, all of which he could relate to.    

All of this to say, Rose’s post-playing career is primed to make an even bigger impact in the world than the one wearing a basketball jersey ever did. Or at least that’s definitely the goal,
as you’ll read below. This chapter of Rose’s life is about stepping out of the comfort zone and entering industries and sectors that once didn’t even seem likely or a match for him. And, so, we thought it was only right that we delivered our interview with the superstar to the world unfiltered, in Q&A format, for everyone to take in directly from Rose, as he looked back at his historic career while also looking ahead into the future.

SLAM: Aside from your social media post, your retirement announcement involved a letter to the game of basketball that ran in newspapers in all the markets you played in. Can you walk us through the thought process behind deciding to announce your retirement in that unique manner? 

Derrick Rose: I feel like it was a team effort. You know, when I first made the decision, of course, I told my two friends, Randall [Hampton] and Maddie [Ornstil] about it and they’re [now] working on my team with me. And Maddie mentioned, What about the newspaper? I didn’t answer right away. That’s something we kept ideating on, and it came together great. But we wanted to give something that was tangible for the fans to actually go out and purchase. Something to have, like a time stamp. I’m a collector now, but I know people that’ve been following my career for numerous years. I know they would’ve loved the opportunity to be a part of that moment. So, putting something out like that into the world, [that’s] tangible and giving you the old-school feel of how things used to be—like the fabric of things back in the day. 

SLAM: Your IG caption for the announcement read: “The psychological assumption automatically provides the means to fulfill the dream desire.” Why did you decide to go with that line for your announcement caption and how would you say that statement relates to your own personal journey?

DR: That’s something that I wrote on my mirror [and] I look at every day. It’s whatever you think you are or whatever you think of, you can actually become it or manifest it. So, it’s just a reminder. I got like five to eight quotes on my mirror that remind me every day. But that one is number one because in order for me to fulfill my dream and desire, it has to be on [my] mind constantly. It has to be an obsession. It has to be intrusive. You can’t just love it, you have to be obsessed with it. And I feel like this process right now is not only me, but my team being obsessed with the journey, the challenge, and just pushing each other to be great. So, we have a goal, [but] I don’t want to say the goal right now, but we have a goal and we have a vision that we’re going to complete. But there’s no point of my stating it right now when we still got a lot of work to do. 

SLAM: Where is that mirror located?

DR: It’s my personal mirror, my bathroom mirror. And I just started that like a few months ago…Like two months ago, recently…Just something that I heard through somebody. It was through a lecture or something like that. And I just tried it just to see how it would work. My wife was looking at me crazy, my kids were looking at me crazy, but, yeah, just pushing myself to be uncomfortable and living in the unknown. 

SLAM: You signed off your retirement letter by saying that the game will always be a part of you, no matter where life takes you. How do you anticipate the game will continue to be a part of you in your post-playing days? 

DR: I feel like being from Chicago is already ingrained in me. I gave my all to the game. That’s one of the reasons I could step away and be happy with stepping away and not feel any resentment or feel down about it. My son plays, my youngest son plays and it’s really me tailor-making their schedule, however I see it’s fit for them. Like, both of my kids play, but I don’t push them to actually go out there. I give them the opportunity to voice their opinion on certain things. So, we’re on the court, You don’t like this drill, what you want to do? And that relationship, it helps a lot with me and PJ, and with my youngest, him seeing PJ work out, too. So, basketball is always going to be a part of my life in general. But my goal, when these years pass, and I keep telling Maddie and Randall this, I want to remove myself from that imagery—where 20, 30 years down the line, I want young guys that play here or when I go visit places, I want them to not know that I played basketball at all because I want to keep completing my goals, and that’s to become a businessman and really to boss up in every area.

SLAM: Are there hobbies or personal interests that you’ve now been able to dedicate time to post-retirement that you maybe didn’t have time to do during your playing days? 

DR: It’s a lot to do with that camera right there. Figuring out if I want to be a director or producer, figuring out the difference between the two, because I always thought that they were the same. But I feel like I’m heading toward the director side, really catching the eye. I feel like I’ve put in the work, I’ve put in tens of thousands of hours in watching documentaries and films, weird docs and great docs. And now it’s all about taking the courage to actually be behind the camera and to voice my opinion. I feel like that’d be the hardest challenge. I’ve also been playing a lot of chess and hopefully somewhere down the line within the next couple of weeks, I’ll ink a chess deal [and] you’ll be hearing about it pretty soon.

SLAM: Where and when did that passion for storytelling originate? 

DR: I will say toward the end of my career, like five or six years ago, knowing that, first, I was into history. I then went from history to me questioning myself, Would you ever think about putting out a doc or putting out stories that are in books that people really don’t tell? And it went from that to me actually getting a camera, me being behind a camera, me being so uncomfortable being behind the camera, talking, multitasking, while I’m behind the camera, and trying to put it all together and being uncomfortable. That’s what I love about just holding a camera. How cool would it have been if it was Michael Jordan or Magic or Michael Jackson behind the camera and it was them shooting everything? It would make the doc a little bit more special, I feel like, instead of them having a crew to shoot it. You hear their voice, the little mess-ups, the errors, everything. I just love raw footage. 

SLAM: You mentioned you enjoy history. Is that something that developed while studying at Simeon or later in life? 

DR: As I got older, it came from my mom. The love of history came from my mom because my mom is big into history, not knowing that I would love it somewhere down the line. But with me figuring out who I was through self- knowledge, self-revelation and self-identity—figuring those three keys out—I started to realize, like, Hey, I’m obsessed with this. I just don’t love it, I’m obsessed with it. I started to cry about certain things that I read. I started to look up or daydream about certain things that I read. And at that moment, that’s how I knew that I was really passionate for it. So, it’s about now translating that over to what that looks like with me finding my eye for certain films or certain things that I want to shoot. And the next step is having the courage to put that out there to present it to the world.

SLAM: I’m sure you’ve had some time to reflect on your playing career over the past couple of months. Looking back, what would you say were your top three on-court moments? 

DR: I would say [winning] MVP. My first game as a rookie. And the third one would be the 50-point game in Minnesota. In that order. 

SLAM: Similarly, having had some time to reflect, what would you say is the biggest life lesson you took away from your playing days that you can now pass on and teach the kids at Simeon? 

DR: I would say to cherish the moment. When you look up the definition of cherish, it means to protect, too. Not only to remember, but to protect. All my best friends that went here, we still talk about Simeon to this day. And now that I’m thinking about it, that’s something that we protected in a way, where, for one, you’re not going to say anything crazy about Simeon when we are around. But also knowing that we now have people in powerful spots here, so that’s our way of being on the ground, always having somebody nearby to protect it. And just knowing that these days, you can’t get them back.

If I could tell the kids, I wish that I could have held on to the memories a little bit more because it was a blur. You win the first [MVP award], that’s already out the window. You want to get to the second [MVP]. I wish I would’ve cherished that first one a little bit more. I wish I would’ve took more pictures, I wish I would’ve had videos. I wish I would have just held on to it. 

SLAM: A big portion of your retirement ceremony weekend will be dedicated to community initiatives around Chicago and local kids. Can you tell us more about some of the initiatives you’d like to do on the community front moving forward? 

DR: For one, coming back here [to Simeon], we’re doing an all-star game event here. This came from—when we were in high school, on this random day, Cam’ron and Dipset had a game here, and it was unexpected. We were about to go home. We didn’t have practice [that day] and to see them pull up in Range Rovers—pink Range Rovers—back there and just had everybody come back to the school, pack out the gym and watch them hoop. I didn’t think of the idea, but Randall ended up asking me, Man, what do you think if we did something like that? And it was a no brainer, we for sure have to do that, but [this time] we’re going to play in it. 

It’s about activations, collaborating with the Bulls and Sloomoo, the slime company, and other partners, to move around the city and make it a real all-star weekend experience.  

SLAM: If 36-year-old Derrick Rose could have a conversation with 22-year-old Derrick Rose, what would you say to him? 

DR: Be patient. When I was younger, I always kept the mindset of like, keep it moving. I call it KIM: keep it moving. And once again, I didn’t cherish those moments because I’m thinking, like, Ah, I won one MVP, next year I’m about to win another one. I’m about to win three or four more. I’m about to win the championship. So, I don’t got time to really celebrate because you hear all the time, once you achieve something, you can’t really bask in it that long. If you do, you’re going to miss out on the next opportunity. I always kept the mindset of, like, keep it moving. But at the same time, looking back at it [now], [I would suggest] just enjoying it. Going to dinner, going to concerts more, events. Really, throwing myself into the matrix. But at that time, I wasn’t ready for that…It was the little things that I overlooked. My third or fourth year—I think it was my fourth year—that’s when I saw Kobe kind of relax. Once I saw that, that’s when I started to relax, because I knew that he wasn’t living the life that he portrayed. Not in a bad way—he wasn’t that intense, I would say.

SLAM: If you had to identify a couple of mentors who helped you stay mentally level-headed through all the ups and downs of your career, who would you say they were and how did they help you? 

DR: For one, my man, Harvey Hampton, that’s my best friend’s dad. He kind of took me in as his third child, [his] family took me in as like their third child. I used to spend the night over at their house almost the entire summer. When I first met him, he threw me for a loop because everybody in my neighborhood that was doing well or had families that were doing well, they were doing nefarious things. I remember being at his house and I asked him straight up, like, Do you sell drugs or something? He started laughing in my face and took me to his office, which is a part of the living room, and was just showing me, like, Nah, I work at a chemical company. I clean the water that you drink, that you bathe in. So, to assume that he was doing nefarious things and for me going there to hear the complete opposite, it kind of blew me away. 

Another guy Dre—Driller—lived in my neighborhood, another guy that was into nefarious things, but changed his life at the right time to help not only in the neighborhood but at Simeon and was one of the coaches at Simeon while we were here. I had another guy that coached along with Harvey, with us in AAU; his name is Lou Tops. And Lou was kind of like the wild card on the team, but taught us heart, bravery and just passion for the game. Coming here, Bob Henry, that was the varsity coach here before I got here. When I came here, I played JV and our coach was Robert Smith. But the varsity coach here, the same guy who coached Benji Wilson, he taught everybody a little bit of something as far as becoming a man, making sure you didn’t mess up in school, making sure that you did think things through, critically thinking and teaching you discipline. That’s the biggest thing I got from here and from all the people that I’ve been around—how disciplined they were.

SLAM: Your retirement weekend will have lots of activations that are meant to celebrate with fans in different capacities. What do you hope people take out of the weekend from an experience standpoint? 

DR: Peace and love, some type of peace and some type of love, or just a vibration. We never thought that we would have an all-star weekend here or host two days here. If we did think that, it was probably a thought that [it’d happen] while I was playing. But to do all of this after the fact, and to conflate everything together and come up with something that’s going to be special and that we could probably turn into an annual thing—you never know. We’re pushing ourselves and we’re getting the most out of every day. It’s a perfect place to be. I call it a great problem. Most people just got problems, but we got great problems. 

SLAM: Twenty, 30 years from now, when people talk to the next generation of kids about your career, what do you hope they remember most about it and the impact you made on the game and on the city of Chicago?

DR: I’d want the question to be, He hooped? I want that one question. I want them to be amazed that I hooped. That’s how far away removed I want to be from it.