A decade of Freelance Wrestling: where high-flying moves meet raw talent

“Two thousand sixteen was the year of my first Freelance Wrestling match. [That] was also the year I was gonna hang it up,” said professional wrestler Mustafa Ali in front of fans at the Logan Square Auditorium in April. A circle of local independent wrestlers who just finished a night of putting their bodies on the line for the sake of entertainment surrounded him in the ring.

Ali is a former World Wrestling Entertainment (WWE) Superstar who cut his teeth in Chicago’s indie wrestling scene more than a decade ago. In April, he competed at the event “In Freelance We Trust,” a bout organized by the Chicago-based independently owned professional wrestling company Freelance Wrestling (FW). The night before this appearance, Ali defeated Japanese wrestler Hiromu Takahashi during Windy City Riot, a professional event organized by New Japan Pro-Wrestling at Wintrust Arena.

Ali is airborne as he executes a finishing move in the ring at Logan Square Auditorium
Ali is airborne as he executes a finishing move. Credit: Alejandro Hernandez

Ali told the sold-out crowd in Logan Square about sending a tape of his debut Freelance Wrestling appearance (a January 2016 title match against Chicago wrestler Isaias Velazquez) to WWE, which led to an invite to their 2016 Cruiserweight Classic tournament.

From 2016 until 2023, Ali wowed WWE fans with high-risk and high-reward maneuvers before transitioning back to the independent scene earlier this year. In February, Ali competed at Total Nonstop Action Wrestling’s (TNA) “No Surrender” annual competition. He won the TNA X Division Championship with this debut appearance.

Freelance X: ten years of Freelance Wrestling
Featuring bouts with wrestlers Storm Grayson, Kylie Rae, Bang & Matthews, Motor City Machine Guns, Darin Corbin, and Koda Hernandez.
Fri 6/28, 8 PM, Logan Square Auditorium, 2539 N. Kedzie, sold out

Ali recounted a 2016 conversation with FW’s founder to the crowd at Logan Square Auditorium that revealed his love of the organization. “I told them, ‘Matt, I got one more year left in me. Just get me in one show because at Freelance,’” he said, voice breaking, “’you guys make us feel fucking alive.’”

FW was founded in 2014 by Nick Almendarez (who wrestles under the name Matt Knicks) and serves as both a proving ground for Chicago’s rising wrestling talent and a stop for traveling wrestlers from major companies.The organization celebrates their tenth anniversary with a sold-out event scheduled for Logan Square Auditorium on June 28. Almendarez never predicted this kind of longevity and success.

a wrestling match at Logan Square Auditorium, two wrestlers are airborne as a ref looks on
Dramatic vistas are part and parcel of the wrestling experience. Credit: Alejandro Hernandez

“I never wanted to be the promoter. I never wanted to be the boss. I just wanted to be a wrestler,” Almendarez told the Reader. “And it kind of grew into this community more than I had intended and, you know, I’m happy and blessed to be a part of something like that.”

Attending a FW show offers a unique and welcoming experience for Chicago’s wrestling fans, particularly those of marginalized backgrounds. Despite its popularity across different cultures, mainstream professional wrestling has historically included problematic and distasteful representations of racial and gender stereotypes, as well as homophobia. FW is an organization that actively addresses those issues. Almendarez said this wasn’t a part of the company’s original mission, but manifested naturally.

The Voice
A Freelance Wrestling event to raise funds for wrestling announcer Kirby Alexander to help offset medical costs after a heart transplant
Sat 7/27, 8 PM, Logan Square Auditorium, 2539 N. Kedzie, $25
More at freelancewrestling.com

“The only real instructions that I give people [who work] on our show is don’t say anything racist, homophobic, or any kind of derogatory remarks like that,” he explained. “It’s not very hard to not do that kind of stuff. We call it ‘cheap heat,’ where you just call someone bad words that you wouldn’t say regularly. You’re able to get your character across in a more organic way, so I think a lot of the talent we book kind of bring that flair with them, and it grows into the atmosphere we have today.”

For April’s “In Freelance We Trust,” one of the night’s most exciting bouts featured a surprise appearance from Sonny Kiss, a Black genderfluid wrestler who gained notoriety for their tenure in All Elite Wrestling (AEW) from 2019 to 2023. Competing in the triple threat match alongside Kiss was Freelance regular Effy, a gay wrestler who wore fishnet stockings and trunks that had “Daddy” written in pink script across the rear. Several of the matches also featured women holding their own against male opponents.

Nick Almendarez poses in front of a wall that holds a framed copy of the Chicago Reader, a 2019 issue with an article on Freelance Wrestling written by Brianna Wellen
Almendarez poses in front of a wall that holds a framed copy of a 2019 issue of the Reader with an article on Freelance Wrestling written by Brianna Wellen Credit: Alejandro Hernandez

Many people’s first impressions of professional wrestling are the televised productions put on by companies like WWE, AEW, and TNA. However, professional wrestling—like music or other creative industries—thrives on the independent scene where talents like Ali first learn the ropes of the wrestling business.

Almendarez takes immense pride in FW being an intermediary space for aspiring wrestlers. He describes the energy transferred from fans as an ebb and flow that the wrestlers feed from. On nights when alumni such as Ali come back and remind the audiences just how important this energy is to them, Almendarez says it helps add perspective.

“In most entertainment fields, it’s very easy to become jaded and lose focus on a lot of things that are important. . . . It makes me feel accomplished,” Almendarez told the Reader. “Ultimately—I’ve told this to our kids at the wrestling school and wrestlers we book—I don’t want to book you forever. I want you to get signed and achieve your dreams and it makes me happy to see that. Then to have them come back and give that love back to us as well—because they don’t have to do that either—it’s awesome and humbling.”


Yes, the Reader likes sports (and sports entertainment)! More from our archives . . .

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