Even in the face of brutal anti-DEI rollbacks, the Chicago White Sox—along with most other Major League Baseball teams—will have a Pride Night to celebrate the LGBTQ+ community. (In fact, the Texas Rangers is the only squad to not host such a designated night.)
On Wed., June 10, the White Sox’s Pride Night will feature, among other things, a very special item. The first 700 ticket purchasers will also receive an official White Sox Pride at the Park Freedom Hat with their purchase specially designed by Tee Sanders—a queer comedian and NAACP’s outstanding digital content creator. Sanders recently talked with Windy City Times about the collaboration, Jason Collins and representation, among other topics.
Note: This conversation was edited for clarity and length.
Windy City Times: I have to congratulate you on your NAACP Image Award. Tell me what it was like when you found out you had won.
Tee Sanders: Oh, man—I don’t think I had processed it. I was so nervous that my heart was beating out of my chest. And as soon as they called my name, all eyes were on me. A few days later, my mom sent me a message from my great-aunt, who’s in the nursery home—and she said, “I knew she was going to do it.”
I just burst out crying, and that’s when it hit me: This is so much bigger to me. The NAACP and what it represents is more than just the war. It represents the history behind Black people and social justice and stuff like that. [My great-aunt has] seen the creation of that. I was so grateful [to win]—so, so grateful.
WCT: And I hate to transition to something sad, but I’m sure you heard about Jason Collins passing. He played a different sport [basketball] but is there anything you want to say about him or what he did?
TS: I’m glad you asked because I saw it and I was, like, “Damn.” Yes, it was very sad [when he passed] but, for some reason, I had just become detached from death. I literally just saw that on Instagram, maybe about 45 minutes ago. But it’s just very clear how much of a trailblazer he was. It’s no different than our Martin Luther Kings. When our civil leaders pass, you [think about] what they provided for us.
WCT: True. Now regarding your partnership with the White Sox, how did it come about?
TS: I’m not sure who introduced me to Michael [Haywood, who works with the White Sox], but Michael had hit me up. Michael hit me up last year to throw the first pitch for Pride Day. So we just stayed connected.
I’m a big hat girl. I got pictures up until I was like 16, 17—girly, straight at the time (or so I thought) and wearing hats. So this is my thing, right? So I thought I would contact Mike because I always wanted to make a White Sox hat. I figured I would just cut out the middleman.
Being a Black lesbian influencer, I figured there were just so many things [the White Sox and I] could do. And I wanted to put my city on the hat because a lot of people didn’t know I was from Chicago—specifically, the South Side.
WCT: And talking about the fans for a moment, the Cubs’ fans always go to home games, regardless of the team’s record. White Sox fans are a bit different.
TS: White Sox fans are not like that. No, baby—we ain’t coming to those trash games. I think it was ‘06 when we won the World Series. [Note: It was actually 2005.] Everybody was in the stands.
I actually learned to love baseball in high school, by accident. We didn’t have cable so I would come home and the only thing that’s on TV was baseball. But I love sports, in general; I played basketball for 10 years. But with baseball, once I started seeing the actual competition of it, I got excited. When I’m at the game—beer in my hand on a hot day, everybody turnt up, with the music and peanuts—it’s everything to me.
WCT: What did you think of the Disco Demolition [that happened at what was then Comiskey Park in 1979]? Because that was the thing that made me more of a Cubs fan than a White Sox fan. It was about what disco represented—the minorities such as the Black and gay people who would dance to that music—and you had people openly destroying those records.
TS: Yeah, but that was a little bit before my time of understanding. It was enough for my parents to understand, but my generation didn’t even really tap into that. But I do remember when the Cubs were the first to start tapping into Pride. But the Cubs were, to me, America’s team. However, when you think about the history of Chicago, we pretty much set the standard for a lot of other cities.
WCT: Now going back to the Freedom hat, there’s so much symbolism with it. There are crossed bats, the Chicago skyline and other items on it. Could you talk about that?
TS: The [bats] just pretty much represent fighting [for equality]. I wanted to showcase because Juneteenth and Pride Month are both in the same space. I wanted to do something that was very Pride-forward but didn’t take away from the fight of what it took to be okay with the rainbow. So that’s kind of where that’s coming into Freedom Day and Stonewall—not backing down. So the hat honors two huge moments for LGBTQ+ equality: the Stonewall Uprising in 1969 and the 2015 Supreme Court ruling on marriage equality.
And you don’t say “I’m from Chicago”; you say, “I’m from the crib.” So there’s a patch that shows that. Again, there’s representation with the Black power fist—even though it’s white on the hat. I didn’t even think about that. [Smiles] And then, of course, there’s the skyline; the flags represent the culture and the community all around, because Chicago is a very open city.
And it was really important for me to make a hat that my straight men didn’t mind wearing. I think I’ve always just been a real bridge and never been a problem being a bridge between the [queer] community and straight people. I didn’t start dating women until my early 20s and I’ve given birth; I have a history with men. And once you have a straight man having your back [as an ally], it gives us and our community wings.
That’s my focus. We all can shine together—no matter where we’re from, no matter what we represent and no matter who we are.
WCT: So what does representation mean to you?
TS: That’s loaded. I didn’t have representation when I grew up but I also learned early not to idolize anyone. I didn’t know the importance of representation until I was in the public eye.
I started getting messages from other masculine-presenting women saying, “Bro, you say exactly what I wish I could—but I can’t because I’m very male-forward.” Then I made videos about me flirting with men and being confused about it because that was my story. So I started representing a different form of masculine-presenting woman—one who’s also very feminine. I have no trouble flirting with men; my energy is very fluid.
Then there were people I’ll just call the “stud police.” They said, “You’re the reason why men don’t respect us.” But it doesn’t matter what clothes you’ve got on—men are men, period.
But it goes back to the NAACP Award—this is all bigger than me. When you become older, you start realizing the impact of every decision you make. In the end, I’ll just say that representation now means having a responsibility to understand people just like you.
Tickets to the 2026 Chicago White Sox Pride Night at the Park are availablehere.
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